Diosmetin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Diosmetin
DrugBank Accession Number
DB11259
Background

Diosmetin is an O-methylated flavone and the aglycone part of the flavonoid glycosides diosmin that occurs naturally in citrus fruits 2. Pharmacologically, diosmetin is reported to exhibit anticancer, antimicrobial, antioxidant, oestrogenic and anti-inflamatory activities 2. It also acts as a weak TrkB receptor agonist 1.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 300.2629
Monoisotopic: 300.063388116
Chemical Formula
C16H12O6
Synonyms
  • 3',5,7-trihydroxy-4'-methoxyflavone
  • 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone
  • Luteolin 4'-methyl ether
  • Salinigricoflavonol

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
ACytochrome P450 1B1
inhibitor
Humans
ASignal transducer and activator of transcription 3
inhibitor
Humans
Absorption

Diosmin is hydrolyzed to its aglycone diosmetin by intestinal microflora enzymes before its absorption into the body 2.

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
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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.
Not Available
Food Interactions
Not Available

Products

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Gingjinhyang Seol WhiteningLotion0.1 mL/100mLTopicalLg Household & Health Care Ltd.2010-04-082011-06-01US flag
Gongjinhyang Seol WhiteningCream0.10 g/100gTopicalLg Household & Health Care Ltd.2010-03-24Not applicableUS flag
Gongjinhyang Seol Whitening EssenceCream0.1 mL/100mLTopicalLg Household & Health Care Ltd.2010-03-262011-06-01US flag
Isa Knox Wxii Plus Whitening Revolution SerumCream0.11 mL/100mLTopicalLg Household & Health Care Ltd.2010-04-23Not applicableUS flag
Isaknox X202 Whitening Secret EssenceCream0.055 mL/100mLTopicalLg Household & Health Care Ltd.2011-06-01Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Gingjinhyang Seol WhiteningDiosmetin (0.1 mL/100mL)LotionTopicalLg Household & Health Care Ltd.2010-04-082011-06-01US flag
Gongjinhyang Seol Whitening EssenceDiosmetin (0.1 mL/100mL)CreamTopicalLg Household & Health Care Ltd.2010-03-262011-06-01US flag
Isaknox X202 Whitening Secret EssenceDiosmetin (0.055 mL/100mL)CreamTopicalLg Household & Health Care Ltd.2011-06-01Not applicableUS flag
Whoo Gongjinhyang Seol Whitening Jin EssenceDiosmetin (0.055 mL/100mL)CreamTopicalLg Household & Health Care Ltd.2010-05-24Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Flavonoids
Sub Class
O-methylated flavonoids
Direct Parent
4'-O-methylated flavonoids
Alternative Parents
3'-hydroxyflavonoids / 5-hydroxyflavonoids / 7-hydroxyflavonoids / Flavones / Chromones / Methoxyphenols / Phenoxy compounds / Methoxybenzenes / Anisoles / 1-hydroxy-2-unsubstituted benzenoids
show 8 more
Substituents
1-benzopyran / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 3'-hydroxyflavonoid / 4p-methoxyflavonoid-skeleton / 5-hydroxyflavonoid / 7-hydroxyflavonoid / Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
monomethoxyflavone, trihydroxyflavone, 3'-hydroxyflavonoid (CHEBI:4630) / flavones, Flavones and Flavonols (C10038) / Flavones and Flavonols (LMPK12110824)
Affected organisms
Not Available

Chemical Identifiers

UNII
TWZ37241OT
CAS number
520-34-3
InChI Key
MBNGWHIJMBWFHU-UHFFFAOYSA-N
InChI
InChI=1S/C16H12O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-7,17-19H,1H3
IUPAC Name
5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
SMILES
COC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C=C2O

References

General References
  1. Jang SW, Liu X, Yepes M, Shepherd KR, Miller GW, Liu Y, Wilson WD, Xiao G, Blanchi B, Sun YE, Ye K: A selective TrkB agonist with potent neurotrophic activities by 7,8-dihydroxyflavone. Proc Natl Acad Sci U S A. 2010 Feb 9;107(6):2687-92. doi: 10.1073/pnas.0913572107. Epub 2010 Jan 25. [Article]
  2. Patel K, Gadewar M, Tahilyani V, Patel DK: A review on pharmacological and analytical aspects of diosmetin: a concise report. Chin J Integr Med. 2013 Oct;19(10):792-800. doi: 10.1007/s11655-013-1595-3. Epub 2013 Oct 4. [Article]
Human Metabolome Database
HMDB0029676
KEGG Compound
C10038
PubChem Compound
5281612
PubChem Substance
347827956
ChemSpider
4444931
BindingDB
23414
RxNav
1314347
ChEBI
4630
ChEMBL
CHEMBL90568
ZINC
ZINC000005733652
PDBe Ligand
J8D
Wikipedia
Diosmetin
PDB Entries
6m8d

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
LotionTopical0.1 mL/100mL
CreamTopical0.10 g/100g
CreamTopical0.1 mL/100mL
CreamTopical0.11 mL/100mL
CreamTopical0.055 mL/100mL
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0754 mg/mLALOGPS
logP3.06ALOGPS
logP2.55Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)6.58Chemaxon
pKa (Strongest Basic)-4.8Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area96.22 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity79.38 m3·mol-1Chemaxon
Polarizability29.84 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0kh9-0492000000-c9cb489c6e399645f54f
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-014u-0000700009-50048523dd30a3c69126
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-014u-0000700009-50048523dd30a3c69126
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSsplash10-057i-0490000000-9c04ed66f8f3ed9e2ed8
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSsplash10-001i-0190000000-77edda567cd76512c52d
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-001i-0090000000-675379707ad9e98244a9
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-0002-0091000000-188fb9f96e76251ce539
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSsplash10-057i-0490000000-9c04ed66f8f3ed9e2ed8
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSsplash10-001i-0190000000-77edda567cd76512c52d
LC-MS/MS Spectrum - LC-ESI-ITTOF , negativeLC-MS/MSsplash10-001i-0090000000-ae5188debe4910fab9c6
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-001i-0090000000-6e1198f4157cda4df0ac
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-001i-0090000000-b23157e3c53d703e88d1
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-001i-0090000000-675379707ad9e98244a9
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-057i-0490000000-9c04ed66f8f3ed9e2ed8
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-001i-0190000000-77edda567cd76512c52d
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0094000000-0b3f48256d5c0ee7fb1b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-05525e1ba993eeb291f5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-47d007256fa8e1d88376
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0290000000-f5c536fdb9391c3c4fa5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0059000000-008c14877809c60c3146
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-056r-0390000000-2b5fa2d9c3b17bb46caf
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-1029-1290000000-f03eaf1046f42811ba2a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-183.3338886
predicted
DarkChem Lite v0.1.0
[M-H]-183.3531886
predicted
DarkChem Lite v0.1.0
[M-H]-183.4594886
predicted
DarkChem Lite v0.1.0
[M-H]-169.99042
predicted
DeepCCS 1.0 (2019)
[M+H]+186.1046886
predicted
DarkChem Lite v0.1.0
[M+H]+186.9491886
predicted
DarkChem Lite v0.1.0
[M+H]+187.4137886
predicted
DarkChem Lite v0.1.0
[M+H]+172.34842
predicted
DeepCCS 1.0 (2019)
[M+Na]+184.0612886
predicted
DarkChem Lite v0.1.0
[M+Na]+184.9671886
predicted
DarkChem Lite v0.1.0
[M+Na]+183.7953886
predicted
DarkChem Lite v0.1.0
[M+Na]+178.85918
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Exhibits catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2- and 4-hydroxy E1 and E2. Displays a predominant hydroxylase activity toward E2 at the C-4 position (PubMed:11555828, PubMed:12865317). Metabolizes testosterone and progesterone to B or D ring hydroxylated metabolites (PubMed:10426814). May act as a major enzyme for all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376, PubMed:15258110). Catalyzes the epoxidation of double bonds of certain PUFA. Converts arachidonic acid toward epoxyeicosatrienoic acid (EpETrE) regioisomers, 8,9-, 11,12-, and 14,15- EpETrE, that function as lipid mediators in the vascular system (PubMed:20972997). Additionally, displays dehydratase activity toward oxygenated eicosanoids hydroperoxyeicosatetraenoates (HpETEs). This activity is independent of cytochrome P450 reductase, NADPH, and O2 (PubMed:21068195). Also involved in the oxidative metabolism of xenobiotics, particularly converting polycyclic aromatic hydrocarbons and heterocyclic aryl amines procarcinogens to DNA-damaging products (PubMed:10426814). Plays an important role in retinal vascular development. Under hyperoxic O2 conditions, promotes retinal angiogenesis and capillary morphogenesis, likely by metabolizing the oxygenated products generated during the oxidative stress. Also, contributes to oxidative homeostasis and ultrastructural organization and function of trabecular meshwork tissue through modulation of POSTN expression (By similarity)
Specific Function
aromatase activity
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Signal transducer and transcription activator that mediates cellular responses to interleukins, KITLG/SCF, LEP and other growth factors (PubMed:10688651, PubMed:12359225, PubMed:12873986, PubMed:15194700, PubMed:15653507, PubMed:16285960, PubMed:17344214, PubMed:18242580, PubMed:18782771, PubMed:22306293, PubMed:23084476, PubMed:28262505, PubMed:32929201). Once activated, recruits coactivators, such as NCOA1 or MED1, to the promoter region of the target gene (PubMed:15653507, PubMed:16285960, PubMed:17344214, PubMed:18782771, PubMed:28262505, PubMed:32929201). May mediate cellular responses to activated FGFR1, FGFR2, FGFR3 and FGFR4 (PubMed:12873986). Upon activation of IL6ST/gp130 signaling by interleukin-6 (IL6), binds to the IL6-responsive elements identified in the promoters of various acute-phase protein genes (PubMed:12359225). Activated by IL31 through IL31RA (PubMed:15194700). Acts as a regulator of inflammatory response by regulating differentiation of naive CD4(+) T-cells into T-helper Th17 or regulatory T-cells (Treg): acetylation promotes its transcription activity and cell differentiation while deacetylation and oxidation of lysine residues by LOXL3 inhibits differentiation (PubMed:28065600, PubMed:28262505). Involved in cell cycle regulation by inducing the expression of key genes for the progression from G1 to S phase, such as CCND1 (PubMed:17344214). Mediates the effects of LEP on melanocortin production, body energy homeostasis and lactation (By similarity). May play an apoptotic role by transctivating BIRC5 expression under LEP activation (PubMed:18242580). Cytoplasmic STAT3 represses macroautophagy by inhibiting EIF2AK2/PKR activity (PubMed:23084476). Plays a crucial role in basal beta cell functions, such as regulation of insulin secretion (By similarity). Following JAK/STAT signaling activation and as part of a complex with NFATC3 and NFATC4, binds to the alpha-beta E4 promoter region of CRYAB and activates transcription in cardiomyocytes (By similarity)
Specific Function
chromatin DNA binding
Gene Name
STAT3
Uniprot ID
P40763
Uniprot Name
Signal transducer and activator of transcription 3
Molecular Weight
88067.215 Da
References
  1. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Drug created at December 03, 2015 16:51 / Updated at August 26, 2024 19:22