Quercetin

Identification

Summary

Quercetin is a natural flavonoid found in foods and natural supplement products.

Generic Name
Quercetin
DrugBank Accession Number
DB04216
Background

Quercetin is a flavonol widely distributed in plants. It is an antioxidant, like many other phenolic heterocyclic compounds. Glycosylated forms include RUTIN and quercetrin.

Type
Small Molecule
Groups
Experimental, Investigational
Structure
Weight
Average: 302.2357
Monoisotopic: 302.042652674
Chemical Formula
C15H10O7
Synonyms
  • 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one
  • 3,3',4',5,7-pentahydroxyflavone
  • 3,5,7,3',4'-Pentahydroxyflavone
  • 3'-HYDROXYKAEMPFEROL
  • FLAVONE, 3,3',4',5,7-PENTAHYDROXY-
  • poly (lactide-co-glycolide)-polyethylene glycol nanoparticles encapsulating quercetin
  • Sophoretin
  • Xanthaurine
External IDs
  • LDN-0052529
  • NSC-57655
  • NSC-9219

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action

Quercetin is a specific quinone reductase 2 (QR2) inhibitor, an enzyme (along with the human QR1 homolog) which catalyzes metabolism of toxic quinolines. Inhibition of QR2 in plasmodium may potentially cause lethal oxidative stress. The inhibition of antioxidant activity in plasmodium may contribute to killing the malaria causing parasites.

TargetActionsOrganism
UPhosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoformNot AvailableHumans
UUDP-glucuronosyltransferase 3A1Not AvailableHumans
UATP synthase subunit alpha, mitochondrialNot AvailableHumans
UATP synthase subunit beta, mitochondrialNot AvailableHumans
UATP synthase subunit gamma, mitochondrialNot AvailableHumans
USerine/threonine-protein kinase pim-1Not AvailableHumans
UHTH-type transcriptional regulator TtgRNot AvailablePseudomonas putida (strain DOT-T1E)
U3-hydroxyisobutyryl-CoA hydrolase, mitochondrialNot AvailableHumans
U3-hydroxyacyl-[acyl-carrier-protein] dehydratase FabZNot AvailableHelicobacter pylori
USerine/threonine-protein kinase 17BNot AvailableHumans
UEstrogen receptor alphaNot AvailableHumans
UEstrogen receptor betaNot AvailableHumans
URibosyldihydronicotinamide dehydrogenase [quinone]
inhibitor
Humans
UAryl hydrocarbon receptorNot AvailableHumans
UCytochrome P450 1B1Not AvailableHumans
UActin, cytoplasmic 1Not AvailableHumans
UCasein kinase II subunit alphaNot AvailableHumans
UCasein kinase II subunit betaNot AvailableHumans
UEukaryotic translation initiation factor 3 subunit FNot AvailableHumans
UHeat shock protein HSP 90-alphaNot AvailableHumans
UHeat shock-related 70 kDa protein 2Not AvailableHumans
URuvB-like 2Not AvailableHumans
USplicing factor 3B subunit 3Not AvailableHumans
UUbiquitin-like modifier-activating enzyme 1Not AvailableHumans
USex hormone-binding globulinNot AvailableHumans
UCarbonyl reductase [NADPH] 1Not AvailableHumans
UCCAAT/enhancer-binding protein beta
inhibitor
Humans
UNuclear receptor subfamily 1 group I member 2
activator
Humans
UTyrosine-protein kinase HCKNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbemaciclibQuercetin may decrease the excretion rate of Abemaciclib which could result in a higher serum level.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Quercetin.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Quercetin.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Quercetin.
AcetohexamideThe metabolism of Acetohexamide can be decreased when combined with Quercetin.
Food Interactions
Not Available

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as flavonols. These are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Flavonoids
Sub Class
Flavones
Direct Parent
Flavonols
Alternative Parents
3'-hydroxyflavonoids / 3-hydroxyflavonoids / 4'-hydroxyflavonoids / 5-hydroxyflavonoids / 7-hydroxyflavonoids / Chromones / Catechols / 1-hydroxy-2-unsubstituted benzenoids / Pyranones and derivatives / 1-hydroxy-4-unsubstituted benzenoids
show 7 more
Substituents
1-benzopyran / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 3'-hydroxyflavonoid / 3-hydroxyflavone / 3-hydroxyflavonoid / 4'-hydroxyflavonoid / 5-hydroxyflavonoid / 7-hydroxyflavonoid / Aromatic heteropolycyclic compound
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
pentahydroxyflavone, 7-hydroxyflavonol (CHEBI:16243) / flavonols, Flavones and Flavonols (C00389) / Flavones and Flavonols (LMPK12110004)
Affected organisms
Not Available

Chemical Identifiers

UNII
9IKM0I5T1E
CAS number
117-39-5
InChI Key
REFJWTPEDVJJIY-UHFFFAOYSA-N
InChI
InChI=1S/C15H10O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,16-19,21H
IUPAC Name
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one
SMILES
OC1=CC2=C(C(O)=C1)C(=O)C(O)=C(O2)C1=CC=C(O)C(O)=C1

References

Synthesis Reference

Miguel M. Taya, Dionisio M. Aedo, Rene Ricard, "Quercetin pentamethyl carbamate and a process for its preparation." U.S. Patent US4202825, issued October, 1975.

US4202825
General References
Not Available
Human Metabolome Database
HMDB0005794
KEGG Compound
C00389
PubChem Compound
5280343
PubChem Substance
46506533
ChemSpider
4444051
BindingDB
7460
RxNav
9060
ChEBI
16243
ChEMBL
CHEMBL50
ZINC
ZINC000003869685
Therapeutic Targets Database
DAP001419
PDBe Ligand
QUE
Wikipedia
Quercetin
PDB Entries
1e8w / 1gp6 / 1h1i / 2c9z / 2hck / 2jj2 / 2ms6 / 2n6c / 2o3p / 2uxh
show 23 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Unknown StatusTreatmentCoronavirus Disease 2019 (COVID‑19)1
4WithdrawnPreventionMenopause related conditions1
3Unknown StatusTreatmentCoronary Artery Disease Progression1
2Active Not RecruitingPreventionFanconi's Anemia / Squamous Cell Carcinoma (SCC)1
2Active Not RecruitingSupportive CareHealthy Volunteers (HV)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • V Sab Medical Labs Inc.
Dosage Forms
FormRouteStrength
TabletOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)316.5 °CPhysProp
water solubility60 mg/L (at 16 °C)SEIDELL,A (1941)
Predicted Properties
PropertyValueSource
Water Solubility0.261 mg/mLALOGPS
logP1.81ALOGPS
logP2.16Chemaxon
logS-3.1ALOGPS
pKa (Strongest Acidic)6.38Chemaxon
pKa (Strongest Basic)-4Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area127.45 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity76.86 m3·mol-1Chemaxon
Polarizability28.54 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.965
Blood Brain Barrier-0.5711
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.5629
P-glycoprotein inhibitor INon-inhibitor0.9297
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterNon-inhibitor0.931
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.653
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.5823
CYP450 2D6 inhibitorNon-inhibitor0.9287
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorInhibitor0.6951
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5822
Ames testNon AMES toxic0.722
CarcinogenicityNon-carcinogens0.945
BiodegradationNot ready biodegradable0.8672
Rat acute toxicity3.0200 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9781
hERG inhibition (predictor II)Non-inhibitor0.8161
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (5 TMS)GC-MSsplash10-0bt9-2611390000-f8e98c928a7ed82acda4
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0079-0591000000-2a146657da898ec9322e
GC-MS Spectrum - GC-MSGC-MSsplash10-0bt9-2611390000-f8e98c928a7ed82acda4
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-0udi-0009000000-d4689b76f41c73487399
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-0udi-0967000000-613e61ec0c69ed0ee630
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0uy0-5910000000-ee816015eec26c8621b1
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, PositiveLC-MS/MSsplash10-0udi-0009000000-ec1cab852ed9f9f78fa4
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0udi-1907000000-6f36df2733dadae380c2
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0udi-0309000000-976a99c106ceca16d73b
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0pi0-1900000000-b2e286366d41e47dd8fc
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0udi-0209000000-e891863ec110aeb660b0
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0udi-0940000000-aa52db00c1defe3ccf75
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0udi-0219000000-5ef285c4b6bfd220b8b1
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0udi-0219000000-547c83bb70e7da007d6c
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0udi-1907000000-a59602c09f66e9656068
LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , PositiveLC-MS/MSsplash10-0udi-0009000000-4416f39adf6c9b919bfa
LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , NegativeLC-MS/MSsplash10-0udi-0019000000-eb14ec62fc2fb2f1da88
LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , NegativeLC-MS/MSsplash10-0ufr-0910000000-0730bca525c17aac75c5
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-004i-0030290000-06238e4a98a4daad3265
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSsplash10-0udi-0039008002-9df3edfb34deb15f8474
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-0udi-0039008002-9df3edfb34deb15f8474
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-0uka-0193000000-3325ca1a080730a9c0bf
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSsplash10-00di-0690000000-fc73e696aa7dda4ed068
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-00di-0690000000-fc73e696aa7dda4ed068
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSsplash10-00di-0690000000-fc73e696aa7dda4ed068
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSsplash10-00di-0690000000-fc73e696aa7dda4ed068
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-00di-0690000000-fc73e696aa7dda4ed068
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSsplash10-00di-0690000000-fc73e696aa7dda4ed068
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSsplash10-0kmi-0920000000-2cd49ad40f2f08fee3ab
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-00di-0090000000-6e7d9bd766aeac1e8423
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSsplash10-0udi-0039008002-9df3edfb34deb15f8474
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-0f6t-0095000000-263e67f066235717bced
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-0uka-0193000000-3325ca1a080730a9c0bf
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSsplash10-00di-0690000000-fc73e696aa7dda4ed068
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-0uk9-0930000000-363b1bf4e9a6499fb535
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSsplash10-014i-0900000000-845f3e731d2cccac16f9
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSsplash10-014i-0900000000-9b75e80bd57dc444dda7
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSsplash10-014i-0900000000-3d57664b65937f1fdbe8
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-0udj-0059000000-4569f9771af75819d4ff
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSsplash10-0f6t-0096000000-8e3b5b434e0a7ac4a6f2
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSsplash10-0kmi-0920000000-2cd49ad40f2f08fee3ab
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0009000000-72d3757130f6362ef16d
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0409000000-a4dcf8e7bf7fc06c6095
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0911000000-26d2681925e713dea7c4
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0uk9-0900000000-5be8620fbd47ec2d1052
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0fk9-0900000000-8ac4420cd3971f9601a6
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0009000000-fb7dfb09272d435ea607
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0903000000-fd4be6f2614be7172a35
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0zmi-1900000000-9b0554a80fe8e8b94408
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0829-8900000000-d5a528d6e21b618ea2b1
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0udi-0915000000-7a3fb3aa5f4be69956d8
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0udi-0910000000-350f78e2382f3fecc61a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0udi-0910000000-ddd05c50a7b3c03051a4
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-1907000000-5aa9a239adad90fab984
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0309000000-976a99c106ceca16d73b
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0pi0-1900000000-272962af7f0845810af5
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0209000000-e891863ec110aeb660b0
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-1907000000-a59602c09f66e9656068
LC-MS/MS Spectrum - LC-ESI-ITTOF , negativeLC-MS/MSsplash10-0ufr-0910000000-0730bca525c17aac75c5
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0912000000-7266f09b33299900ac8e
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0109000000-b493a0a82085432cebf6
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udi-0019000000-c0d60f99f3eee7a22cd0
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udi-1149000000-3599b5960dcb4fc954ce
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udi-0924000000-366e21015025ab5b67e3
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0ufr-0924000000-fc5bd30ed53f393e6bc1
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0fb9-0923000000-fe0fe51fc455246b02f1
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0ufr-0924000000-7ce36c0fa7ed55a80faa
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0fb9-0920000000-924a81fa0a3ac1416373
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0fb9-0920000000-5e828a169697753324ed
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udi-0009000000-4250e78673758d7495f7
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udi-0009000000-c01afcb240931742dcf0
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-00di-0090000000-6e7d9bd766aeac1e8423
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0uka-0193000000-3325ca1a080730a9c0bf
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-00di-0690000000-fc73e696aa7dda4ed068
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0uk9-0930000000-363b1bf4e9a6499fb535
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-014i-0900000000-845f3e731d2cccac16f9
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-014i-0900000000-9b75e80bd57dc444dda7
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-014i-0900000000-3d57664b65937f1fdbe8
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0udj-0059000000-4569f9771af75819d4ff
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0kmi-0920000000-2cd49ad40f2f08fee3ab
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0009000000-928c8675170aaec9b91b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0009000000-d6fa322373b1a4fa5481
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0119000000-240815bff9a5d73c6d37
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0972000000-4c22f12734e1fc833e7a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0930000000-fc811aa14c3f21dd2d87
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0009000000-8653f7bcf5d38cee7445
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0009000000-f3f724fc952cbc28c800
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0ufr-0961000000-fb42c6414c6952f1e4b0
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0zi0-1910000000-86be3c6959d182874340
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0459000000-0d9988aa4ad6d4f3877f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0972000000-03a26fc17df5ae92e2bc
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0ug0-0940000000-eab382a0773efbd9b2fe
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0009000000-05f27218845a61a2bfe0
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0009000000-6db00d86c62d1532dd1f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0029000000-1e32d3a4d88d86d283a2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0229000000-c4a54f710dfb4852d57d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0139000000-4ec0ac744a93b064c5d4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0397000000-617019adfc8fd573e507
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0zi0-0393000000-acd8c0ff694dd2729721
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0940000000-08108f5a3b41c8cbfaa4
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0319000000-5ef285c4b6bfd220b8b1
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0219000000-547c83bb70e7da007d6c
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0ar9-0490000000-0d329f4c9007747360e0
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0ar9-0390000000-0c50e68e5a690203126b
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0as0-0390000000-6f746310e7a6571c58e5
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0009000000-73921279033638fe4d62
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0zg0-0393000000-c537b515119597ee9ce8
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-102i-0392000000-fc41fbc6d925de8102d1
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0as0-0290000000-4158af53d0ebb09e774f
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0ar9-0390000000-161921c02329eabfc797
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0bw9-0490000000-e5bf1722511e153aff65
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0bvr-0390000000-197d114a9278c0e2612a
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00di-0069000000-6dd55093362f957e659e
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00di-0069000000-b8c19af3c8a71771daf8
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0032-0001972000-01954ed9f56878d69e84
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0095-0002972000-7e43cd97850471788609
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-0009000000-d5a15ff9735e3c526282
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-0009000000-de714935daaf0eeba0ce
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a4i-0390000000-87d30204432f9e209880
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a6r-0390000000-5fe461c56b458083044f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-0129000000-7ce37e7933aa2c84cd6f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-0639000000-c7898f09f3583402c20c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-a58be846dd894fbc7daf
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-6d6d59e95fc86145b33f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-46ca5fd25b1d9e1b8629
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0289000000-cc9a7dac81ebf0d02b96
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pb9-0690000000-8a7c96f3f88ddfae2de3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000l-0960000000-2976c9656498a1e9ef6c
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-180.9728845
predicted
DarkChem Lite v0.1.0
[M-H]-162.8392822
predicted
DarkChem Standard v0.1.0
[M-H]-167.7951469
predicted
DarkChem Lite v0.1.0
[M-H]-181.5542845
predicted
DarkChem Lite v0.1.0
[M-H]-181.3557845
predicted
DarkChem Lite v0.1.0
[M-H]-169.74606
predicted
DeepCCS 1.0 (2019)
[M+H]+179.2740845
predicted
DarkChem Lite v0.1.0
[M+H]+164.904221
predicted
DarkChem Standard v0.1.0
[M+H]+170.223561
predicted
DarkChem Lite v0.1.0
[M+H]+182.5602845
predicted
DarkChem Lite v0.1.0
[M+H]+177.2410845
predicted
DarkChem Lite v0.1.0
[M+H]+172.10406
predicted
DeepCCS 1.0 (2019)
[M+Na]+176.4729845
predicted
DarkChem Lite v0.1.0
[M+Na]+176.7530845
predicted
DarkChem Lite v0.1.0
[M+Na]+173.9441599
predicted
DarkChem Lite v0.1.0
[M+Na]+182.1622845
predicted
DarkChem Lite v0.1.0
[M+Na]+176.6825845
predicted
DarkChem Lite v0.1.0
[M+Na]+178.69855
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein serine/threonine kinase activity
Specific Function
Phosphoinositide-3-kinase (PI3K) that phosphorylates PtdIns(4,5)P2 (Phosphatidylinositol 4,5-bisphosphate) to generate phosphatidylinositol 3,4,5-trisphosphate (PIP3). PIP3 plays a key role by recr...
Gene Name
PIK3CG
Uniprot ID
P48736
Uniprot Name
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform
Molecular Weight
126452.625 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Udp-glycosyltransferase activity
Specific Function
UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. The...
Gene Name
UGT3A1
Uniprot ID
Q6NUS8
Uniprot Name
UDP-glucuronosyltransferase 3A1
Molecular Weight
59150.34 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transmembrane transporter activity
Specific Function
Mitochondrial membrane ATP synthase (F(1)F(0) ATP synthase or Complex V) produces ATP from ADP in the presence of a proton gradient across the membrane which is generated by electron transport comp...
Gene Name
ATP5A1
Uniprot ID
P25705
Uniprot Name
ATP synthase subunit alpha, mitochondrial
Molecular Weight
59750.06 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
Mitochondrial membrane ATP synthase (F(1)F(0) ATP synthase or Complex V) produces ATP from ADP in the presence of a proton gradient across the membrane which is generated by electron transport comp...
Gene Name
ATP5B
Uniprot ID
P06576
Uniprot Name
ATP synthase subunit beta, mitochondrial
Molecular Weight
56559.42 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transmembrane transporter activity
Specific Function
Mitochondrial membrane ATP synthase (F(1)F(0) ATP synthase or Complex V) produces ATP from ADP in the presence of a proton gradient across the membrane which is generated by electron transport comp...
Gene Name
ATP5C1
Uniprot ID
P36542
Uniprot Name
ATP synthase subunit gamma, mitochondrial
Molecular Weight
32995.665 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcription factor binding
Specific Function
Proto-oncogene with serine/threonine kinase activity involved in cell survival and cell proliferation and thus providing a selective advantage in tumorigenesis. Exerts its oncogenic activity throug...
Gene Name
PIM1
Uniprot ID
P11309
Uniprot Name
Serine/threonine-protein kinase pim-1
Molecular Weight
45411.905 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Pseudomonas putida (strain DOT-T1E)
Pharmacological action
Unknown
General Function
Dna binding
Specific Function
Represses expression from the ttgABC operon promoter and its own expression. Binds to a promoter region between the divergently transcribed ttgR and ttgABC genes/operons; in the presence of chloram...
Gene Name
ttgR
Uniprot ID
Q9AIU0
Uniprot Name
HTH-type transcriptional regulator TtgR
Molecular Weight
23854.075 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Hydro-lyase activity
Specific Function
Hydrolyzes 3-hydroxyisobutyryl-CoA (HIBYL-CoA), a saline catabolite. Has high activity toward isobutyryl-CoA. Could be an isobutyryl-CoA dehydrogenase that functions in valine catabolism. Also hydr...
Gene Name
HIBCH
Uniprot ID
Q6NVY1
Uniprot Name
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial
Molecular Weight
43481.935 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Helicobacter pylori
Pharmacological action
Unknown
General Function
3-hydroxyoctanoyl-[acyl-carrier-protein] dehydratase activity
Specific Function
Involved in unsaturated fatty acids biosynthesis. Catalyzes the dehydration of short chain beta-hydroxyacyl-ACPs and long chain saturated and unsaturated beta-hydroxyacyl-ACPs.Involved in unsaturat...
Gene Name
fabZ
Uniprot ID
Q5G940
Uniprot Name
3-hydroxyacyl-[acyl-carrier-protein] dehydratase FabZ
Molecular Weight
18184.08 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein serine/threonine kinase activity
Specific Function
Phosphorylates myosin light chains (By similarity). Acts as a positive regulator of apoptosis.
Gene Name
STK17B
Uniprot ID
O94768
Uniprot Name
Serine/threonine-protein kinase 17B
Molecular Weight
42343.595 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Maggiolini M, Bonofiglio D, Marsico S, Panno ML, Cenni B, Picard D, Ando S: Estrogen receptor alpha mediates the proliferative but not the cytotoxic dose-dependent effects of two major phytoestrogens on human breast cancer cells. Mol Pharmacol. 2001 Sep;60(3):595-602. [Article]
  2. Leung LK, Po LS, Lau TY, Yuen YM: Effect of dietary flavonols on oestrogen receptor transactivation and cell death induction. Br J Nutr. 2004 Jun;91(6):831-9. [Article]
  3. van der Woude H, Ter Veld MG, Jacobs N, van der Saag PT, Murk AJ, Rietjens IM: The stimulation of cell proliferation by quercetin is mediated by the estrogen receptor. Mol Nutr Food Res. 2005 Aug;49(8):763-71. [Article]
  4. Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, van der Burg B, Gustafsson JA: Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology. 1998 Oct;139(10):4252-63. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent m...
Gene Name
ESR2
Uniprot ID
Q92731
Uniprot Name
Estrogen receptor beta
Molecular Weight
59215.765 Da
References
  1. Maggiolini M, Bonofiglio D, Marsico S, Panno ML, Cenni B, Picard D, Ando S: Estrogen receptor alpha mediates the proliferative but not the cytotoxic dose-dependent effects of two major phytoestrogens on human breast cancer cells. Mol Pharmacol. 2001 Sep;60(3):595-602. [Article]
  2. Leung LK, Po LS, Lau TY, Yuen YM: Effect of dietary flavonols on oestrogen receptor transactivation and cell death induction. Br J Nutr. 2004 Jun;91(6):831-9. [Article]
  3. van der Woude H, Ter Veld MG, Jacobs N, van der Saag PT, Murk AJ, Rietjens IM: The stimulation of cell proliferation by quercetin is mediated by the estrogen receptor. Mol Nutr Food Res. 2005 Aug;49(8):763-71. [Article]
  4. Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, van der Burg B, Gustafsson JA: Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology. 1998 Oct;139(10):4252-63. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Nadph dehydrogenase (quinone) activity
Specific Function
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vi...
Gene Name
NQO2
Uniprot ID
P16083
Uniprot Name
Ribosyldihydronicotinamide dehydrogenase [quinone]
Molecular Weight
25918.4 Da
References
  1. Buryanovskyy L, Fu Y, Boyd M, Ma Y, Hsieh TC, Wu JM, Zhang Z: Crystal structure of quinone reductase 2 in complex with resveratrol. Biochemistry. 2004 Sep 14;43(36):11417-26. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcription regulatory region dna binding
Specific Function
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes...
Gene Name
AHR
Uniprot ID
P35869
Uniprot Name
Aryl hydrocarbon receptor
Molecular Weight
96146.705 Da
References
  1. Flaveny CA, Murray IA, Chiaro CR, Perdew GH: Ligand selectivity and gene regulation by the human aryl hydrocarbon receptor in transgenic mice. Mol Pharmacol. 2009 Jun;75(6):1412-20. doi: 10.1124/mol.109.054825. Epub 2009 Mar 19. [Article]
Details
15. Cytochrome P450 1B1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Shimada T, Tanaka K, Takenaka S, Murayama N, Martin MV, Foroozesh MK, Yamazaki H, Guengerich FP, Komori M: Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives. Chem Res Toxicol. 2010 Dec 20;23(12):1921-35. doi: 10.1021/tx100286d. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tat protein binding
Specific Function
Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.
Gene Name
ACTB
Uniprot ID
P60709
Uniprot Name
Actin, cytoplasmic 1
Molecular Weight
41736.37 Da
References
  1. Wang RE, Hunt CR, Chen J, Taylor JS: Biotinylated quercetin as an intrinsic photoaffinity proteomics probe for the identification of quercetin target proteins. Bioorg Med Chem. 2011 Aug 15;19(16):4710-20. doi: 10.1016/j.bmc.2011.07.005. Epub 2011 Jul 13. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein serine/threonine kinase activity
Specific Function
Catalytic subunit of a constitutively active serine/threonine-protein kinase complex that phosphorylates a large number of substrates containing acidic residues C-terminal to the phosphorylated ser...
Gene Name
CSNK2A1
Uniprot ID
P68400
Uniprot Name
Casein kinase II subunit alpha
Molecular Weight
45143.25 Da
References
  1. Wang RE, Hunt CR, Chen J, Taylor JS: Biotinylated quercetin as an intrinsic photoaffinity proteomics probe for the identification of quercetin target proteins. Bioorg Med Chem. 2011 Aug 15;19(16):4710-20. doi: 10.1016/j.bmc.2011.07.005. Epub 2011 Jul 13. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcription factor binding
Specific Function
Participates in Wnt signaling (By similarity). Plays a complex role in regulating the basal catalytic activity of the alpha subunit.
Gene Name
CSNK2B
Uniprot ID
P67870
Uniprot Name
Casein kinase II subunit beta
Molecular Weight
24942.25 Da
References
  1. Wang RE, Hunt CR, Chen J, Taylor JS: Biotinylated quercetin as an intrinsic photoaffinity proteomics probe for the identification of quercetin target proteins. Bioorg Med Chem. 2011 Aug 15;19(16):4710-20. doi: 10.1016/j.bmc.2011.07.005. Epub 2011 Jul 13. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Component of the eukaryotic translation initiation factor 3 (eIF-3) complex, which is required for several steps in the initiation of protein synthesis (PubMed:17581632, PubMed:25849773, PubMed:27462815). The eIF-3 complex associates with the 40S ribosome and facilitates the recruitment of eIF-1, eIF-1A, eIF-2:GTP:methionyl-tRNAi and eIF-5 to form the 43S pre-initiation complex (43S PIC). The eIF-3 complex stimulates mRNA recruitment to the 43S PIC and scanning of the mRNA for AUG recognition. The eIF-3 complex is also required for disassembly and recycling of post-termination ribosomal complexes and subsequently prevents premature joining of the 40S and 60S ribosomal subunits prior to initiation (PubMed:17581632). The eIF-3 complex specifically targets and initiates translation of a subset of mRNAs involved in cell proliferation, including cell cycling, differentiation and apoptosis, and uses different modes of RNA stem-loop binding to exert either translational activation or repression (PubMed:25849773).
Specific Function
Thiol-dependent ubiquitin-specific protease activity
Gene Name
EIF3F
Uniprot ID
O00303
Uniprot Name
Eukaryotic translation initiation factor 3 subunit F
Molecular Weight
37563.48 Da
References
  1. Wang RE, Hunt CR, Chen J, Taylor JS: Biotinylated quercetin as an intrinsic photoaffinity proteomics probe for the identification of quercetin target proteins. Bioorg Med Chem. 2011 Aug 15;19(16):4710-20. doi: 10.1016/j.bmc.2011.07.005. Epub 2011 Jul 13. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tpr domain binding
Specific Function
Molecular chaperone that promotes the maturation, structural maintenance and proper regulation of specific target proteins involved for instance in cell cycle control and signal transduction. Under...
Gene Name
HSP90AA1
Uniprot ID
P07900
Uniprot Name
Heat shock protein HSP 90-alpha
Molecular Weight
84659.015 Da
References
  1. Wang RE, Hunt CR, Chen J, Taylor JS: Biotinylated quercetin as an intrinsic photoaffinity proteomics probe for the identification of quercetin target proteins. Bioorg Med Chem. 2011 Aug 15;19(16):4710-20. doi: 10.1016/j.bmc.2011.07.005. Epub 2011 Jul 13. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Molecular chaperone implicated in a wide variety of cellular processes, including protection of the proteome from stress, folding and transport of newly synthesized polypeptides, activation of proteolysis of misfolded proteins and the formation and dissociation of protein complexes. Plays a pivotal role in the protein quality control system, ensuring the correct folding of proteins, the re-folding of misfolded proteins and controlling the targeting of proteins for subsequent degradation. This is achieved through cycles of ATP binding, ATP hydrolysis and ADP release, mediated by co-chaperones. The affinity for polypeptides is regulated by its nucleotide bound state. In the ATP-bound form, it has a low affinity for substrate proteins. However, upon hydrolysis of the ATP to ADP, it undergoes a conformational change that increases its affinity for substrate proteins. It goes through repeated cycles of ATP hydrolysis and nucleotide exchange, which permits cycles of substrate binding and release (PubMed:26865365). Plays a role in spermatogenesis. In association with SHCBP1L may participate in the maintenance of spindle integrity during meiosis in male germ cells (By similarity).
Specific Function
Atp binding
Gene Name
HSPA2
Uniprot ID
P54652
Uniprot Name
Heat shock-related 70 kDa protein 2
Molecular Weight
70020.43 Da
References
  1. Wang RE, Hunt CR, Chen J, Taylor JS: Biotinylated quercetin as an intrinsic photoaffinity proteomics probe for the identification of quercetin target proteins. Bioorg Med Chem. 2011 Aug 15;19(16):4710-20. doi: 10.1016/j.bmc.2011.07.005. Epub 2011 Jul 13. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Possesses single-stranded DNA-stimulated ATPase and ATP-dependent DNA helicase (5' to 3') activity; hexamerization is thought to be critical for ATP hydrolysis and adjacent subunits in the ring-like structure contribute to the ATPase activity.
Specific Function
Adp binding
Gene Name
RUVBL2
Uniprot ID
Q9Y230
Uniprot Name
RuvB-like 2
Molecular Weight
51156.08 Da
References
  1. Wang RE, Hunt CR, Chen J, Taylor JS: Biotinylated quercetin as an intrinsic photoaffinity proteomics probe for the identification of quercetin target proteins. Bioorg Med Chem. 2011 Aug 15;19(16):4710-20. doi: 10.1016/j.bmc.2011.07.005. Epub 2011 Jul 13. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Subunit of the splicing factor SF3B required for 'A' complex assembly formed by the stable binding of U2 snRNP to the branchpoint sequence (BPS) in pre-mRNA. Sequence independent binding of SF3A/SF3B complex upstream of the branch site is essential, it may anchor U2 snRNP to the pre-mRNA. May also be involved in the assembly of the 'E' complex. Belongs also to the minor U12-dependent spliceosome, which is involved in the splicing of rare class of nuclear pre-mRNA intron.
Specific Function
Protein complex binding
Gene Name
SF3B3
Uniprot ID
Q15393
Uniprot Name
Splicing factor 3B subunit 3
Molecular Weight
135576.25 Da
References
  1. Wang RE, Hunt CR, Chen J, Taylor JS: Biotinylated quercetin as an intrinsic photoaffinity proteomics probe for the identification of quercetin target proteins. Bioorg Med Chem. 2011 Aug 15;19(16):4710-20. doi: 10.1016/j.bmc.2011.07.005. Epub 2011 Jul 13. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ubiquitin-protein transferase activity
Specific Function
Catalyzes the first step in ubiquitin conjugation to mark cellular proteins for degradation through the ubiquitin-proteasome system (PubMed:1606621, PubMed:1447181). Activates ubiquitin by first ad...
Gene Name
UBA1
Uniprot ID
P22314
Uniprot Name
Ubiquitin-like modifier-activating enzyme 1
Molecular Weight
117848.075 Da
References
  1. Wang RE, Hunt CR, Chen J, Taylor JS: Biotinylated quercetin as an intrinsic photoaffinity proteomics probe for the identification of quercetin target proteins. Bioorg Med Chem. 2011 Aug 15;19(16):4710-20. doi: 10.1016/j.bmc.2011.07.005. Epub 2011 Jul 13. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. Hong H, Branham WS, Ng HW, Moland CL, Dial SL, Fang H, Perkins R, Sheehan D, Tong W: Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and alpha-fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Curator comments
Non-competitive inhibitor
General Function
Prostaglandin-e2 9-reductase activity
Specific Function
NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. ...
Gene Name
CBR1
Uniprot ID
P16152
Uniprot Name
Carbonyl reductase [NADPH] 1
Molecular Weight
30374.73 Da
References
  1. Hintzpeter J, Hornung J, Ebert B, Martin HJ, Maser E: Curcumin is a tight-binding inhibitor of the most efficient human daunorubicin reductase--Carbonyl reductase 1. Chem Biol Interact. 2015 Jun 5;234:162-8. doi: 10.1016/j.cbi.2014.12.019. Epub 2014 Dec 22. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transcriptional activator activity, rna polymerase ii core promoter proximal region sequence-specific binding
Specific Function
Important transcription factor regulating the expression of genes involved in immune and inflammatory responses (PubMed:9374525, PubMed:12048245, PubMed:18647749). Plays also a significant role in ...
Gene Name
CEBPB
Uniprot ID
P17676
Uniprot Name
CCAAT/enhancer-binding protein beta
Molecular Weight
36105.36 Da
References
  1. Shimizu M, Li J, Inoue J, Sato R: Quercetin represses apolipoprotein B expression by inhibiting the transcriptional activity of C/EBPbeta. PLoS One. 2015 Apr 15;10(4):e0121784. doi: 10.1371/journal.pone.0121784. eCollection 2015. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Lau AJ, Chang TK: 3-Hydroxyflavone and structural analogues differentially activate pregnane X receptor: Implication for inflammatory bowel disease. Pharmacol Res. 2015 Oct;100:64-72. doi: 10.1016/j.phrs.2015.07.031. Epub 2015 Jul 31. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Receptor binding
Specific Function
Non-receptor tyrosine-protein kinase found in hematopoietic cells that transmits signals from cell surface receptors and plays an important role in the regulation of innate immune responses, includ...
Gene Name
HCK
Uniprot ID
P08631
Uniprot Name
Tyrosine-protein kinase HCK
Molecular Weight
59599.355 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [Article]
  2. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Elbarbry F, Ung A, Abdelkawy K: Studying the Inhibitory Effect of Quercetin and Thymoquinone on Human Cytochrome P450 Enzyme Activities. Pharmacogn Mag. 2018 Jan;13(Suppl 4):S895-S899. doi: 10.4103/0973-1296.224342. Epub 2018 Jan 31. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Bedada SK, Neerati P: Evaluation of the effect of quercetin treatment on CYP2C9 enzyme activity of diclofenac in healthy human volunteers. Phytother Res. 2018 Feb;32(2):305-311. doi: 10.1002/ptr.5978. Epub 2017 Nov 23. [Article]
  2. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Bedada SK, Neerati P: The effect of quercetin on the pharmacokinetics of chlorzoxazone, a CYP2E1 substrate, in healthy subjects. Eur J Clin Pharmacol. 2018 Jan;74(1):91-97. doi: 10.1007/s00228-017-2345-9. Epub 2017 Oct 5. [Article]
  2. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Elbarbry F, Ung A, Abdelkawy K: Studying the Inhibitory Effect of Quercetin and Thymoquinone on Human Cytochrome P450 Enzyme Activities. Pharmacogn Mag. 2018 Jan;13(Suppl 4):S895-S899. doi: 10.4103/0973-1296.224342. Epub 2018 Jan 31. [Article]
  2. Flockhart Table of Drug Interactions [Link]
Kind
Protein group
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...

Components:
References
  1. Flockhart Table of Drug Interactions [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Kaldas MI, Walle UK, van der Woude H, McMillan JM, Walle T: Covalent binding of the flavonoid quercetin to human serum albumin. J Agric Food Chem. 2005 May 18;53(10):4194-7. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Kauffmann HM, Pfannschmidt S, Zoller H, Benz A, Vorderstemann B, Webster JI, Schrenk D: Influence of redox-active compounds and PXR-activators on human MRP1 and MRP2 gene expression. Toxicology. 2002 Feb 28;171(2-3):137-46. [Article]
  2. Leslie EM, Mao Q, Oleschuk CJ, Deeley RG, Cole SP: Modulation of multidrug resistance protein 1 (MRP1/ABCC1) transport and atpase activities by interaction with dietary flavonoids. Mol Pharmacol. 2001 May;59(5):1171-80. [Article]
  3. Nguyen H, Zhang S, Morris ME: Effect of flavonoids on MRP1-mediated transport in Panc-1 cells. J Pharm Sci. 2003 Feb;92(2):250-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Bock KW, Eckle T, Ouzzine M, Fournel-Gigleux S: Coordinate induction by antioxidants of UDP-glucuronosyltransferase UGT1A6 and the apical conjugate export pump MRP2 (multidrug resistance protein 2) in Caco-2 cells. Biochem Pharmacol. 2000 Mar 1;59(5):467-70. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucin...
Gene Name
SLC16A7
Uniprot ID
O60669
Uniprot Name
Monocarboxylate transporter 2
Molecular Weight
52199.745 Da
References
  1. Broer S, Broer A, Schneider HP, Stegen C, Halestrap AP, Deitmer JW: Characterization of the high-affinity monocarboxylate transporter MCT2 in Xenopus laevis oocytes. Biochem J. 1999 Aug 1;341 ( Pt 3):529-35. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76709.98 Da
References
  1. Satoh H, Yamashita F, Tsujimoto M, Murakami H, Koyabu N, Ohtani H, Sawada Y: Citrus juices inhibit the function of human organic anion-transporting polypeptide OATP-B. Drug Metab Dispos. 2005 Apr;33(4):518-23. Epub 2005 Jan 7. [Article]
Details
5. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Shapiro AB, Ling V: Effect of quercetin on Hoechst 33342 transport by purified and reconstituted P-glycoprotein. Biochem Pharmacol. 1997 Feb 21;53(4):587-96. [Article]
  2. Eagling VA, Profit L, Back DJ: Inhibition of the CYP3A4-mediated metabolism and P-glycoprotein-mediated transport of the HIV-1 protease inhibitor saquinavir by grapefruit juice components. Br J Clin Pharmacol. 1999 Oct;48(4):543-52. [Article]
  3. Choi CH, Kim JH, Kim SH: Reversal of P-glycoprotein-mediated MDR by 5,7,3',4',5'-pentamethoxyflavone and SAR. Biochem Biophys Res Commun. 2004 Jul 30;320(3):672-9. [Article]
  4. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [Article]
  5. Youdim KA, Qaiser MZ, Begley DJ, Rice-Evans CA, Abbott NJ: Flavonoid permeability across an in situ model of the blood-brain barrier. Free Radic Biol Med. 2004 Mar 1;36(5):592-604. [Article]
  6. Borska S, Sopel M, Chmielewska M, Zabel M, Dziegiel P: Quercetin as a potential modulator of P-glycoprotein expression and function in cells of human pancreatic carcinoma line resistant to daunorubicin. Molecules. 2010 Feb 9;15(2):857-70. doi: 10.3390/molecules15020857. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucin...
Gene Name
SLC16A1
Uniprot ID
P53985
Uniprot Name
Monocarboxylate transporter 1
Molecular Weight
53943.685 Da
References
  1. Broer S, Broer A, Schneider HP, Stegen C, Halestrap AP, Deitmer JW: Characterization of the high-affinity monocarboxylate transporter MCT2 in Xenopus laevis oocytes. Biochem J. 1999 Aug 1;341 ( Pt 3):529-35. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Zhang S, Yang X, Morris ME: Flavonoids are inhibitors of breast cancer resistance protein (ABCG2)-mediated transport. Mol Pharmacol. 2004 May;65(5):1208-16. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Karlgren M, Ahlin G, Bergstrom CA, Svensson R, Palm J, Artursson P: In vitro and in silico strategies to identify OATP1B1 inhibitors and predict clinical drug-drug interactions. Pharm Res. 2012 Feb;29(2):411-26. doi: 10.1007/s11095-011-0564-9. Epub 2011 Aug 23. [Article]

Drug created at June 13, 2005 13:24 / Updated at July 18, 2023 22:56