NAV

Thymoquinone

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

Identification

Generic Name
Thymoquinone
DrugBank Accession Number
DB16447
Background

Thymoquinone is a natural compound with widespread protective effects, including anti-oxidative, anti-inflammatory, immunomodulatory, anti-cancer, and anti-microbial.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 164.204
Monoisotopic: 164.083729626
Chemical Formula
C10H12O2
Synonyms
  • 2-Isopropyl-5-methyl-p-benzoquinone
  • p-Cymene-2,5-dione
  • p-Mentha-3,6-diene-2,5-dione
  • Thymoquinon
External IDs
  • NSC-2228
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action

Thymoquinone is a natural compound with widespread protective effects, including anti-oxidative, anti-inflammatory, immunomodulatory, anti-cancer, and anti-microbial. It is able to induce apoptosis, regulate pro- and anti- apopotitic genes, and inhibit cancer metastasis through JNK and p38 activation. Its anti-inflammatory effects are attributed to its inhibition of inflammatory cytokines and processes, including pathways associated with 5-LO, COX, and PGD2.

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
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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

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
O60IE26NUF
CAS number
490-91-5
InChI Key
KEQHJBNSCLWCAE-UHFFFAOYSA-N
InChI
InChI=1S/C10H12O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h4-6H,1-3H3
IUPAC Name
2-methyl-5-(propan-2-yl)cyclohexa-2,5-diene-1,4-dione
SMILES
CC(C)C1=CC(=O)C(C)=CC1=O

References

General References
  1. Shaterzadeh-Yazdi H, Noorbakhsh MF, Hayati F, Samarghandian S, Farkhondeh T: Immunomodulatory and Anti-inflammatory Effects of Thymoquinone. Cardiovasc Hematol Disord Drug Targets. 2018;18(1):52-60. doi: 10.2174/1871529X18666180212114816. [Article]
  2. Imran M, Rauf A, Khan IA, Shahbaz M, Qaisrani TB, Fatmawati S, Abu-Izneid T, Imran A, Rahman KU, Gondal TA: Thymoquinone: A novel strategy to combat cancer: A review. Biomed Pharmacother. 2018 Oct;106:390-402. doi: 10.1016/j.biopha.2018.06.159. Epub 2018 Jul 11. [Article]
  3. Darakhshan S, Bidmeshki Pour A, Hosseinzadeh Colagar A, Sisakhtnezhad S: Thymoquinone and its therapeutic potentials. Pharmacol Res. 2015 May-Jun;95-96:138-58. doi: 10.1016/j.phrs.2015.03.011. Epub 2015 Mar 28. [Article]
  4. Velagapudi R, El-Bakoush A, Lepiarz I, Ogunrinade F, Olajide OA: AMPK and SIRT1 activation contribute to inhibition of neuroinflammation by thymoquinone in BV2 microglia. Mol Cell Biochem. 2017 Nov;435(1-2):149-162. doi: 10.1007/s11010-017-3064-3. Epub 2017 May 27. [Article]
  5. Gholamnezhad Z, Havakhah S, Boskabady MH: Preclinical and clinical effects of Nigella sativa and its constituent, thymoquinone: A review. J Ethnopharmacol. 2016 Aug 22;190:372-86. doi: 10.1016/j.jep.2016.06.061. Epub 2016 Jun 27. [Article]
Human Metabolome Database
HMDB0034732
ChemSpider
9861
BindingDB
166686
ChEBI
113532
ChEMBL
CHEMBL1672002
ZINC
ZINC000000164367
PDBe Ligand
IMW
Wikipedia
Thymoquinone
PDB Entries
4hco

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentPremalignant Lesion1
2, 3CompletedTreatmentCoronavirus Disease 2019 (COVID‑19) / Immunodeficiencies1
2, 3CompletedTreatmentPolycystic Ovarian Syndrome (PCOS)1
0Not Yet RecruitingTreatmentGingivitis1
Not AvailableNot Yet RecruitingTreatmentChronic Sinusitis / Nasal Polyps1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
logP2.55Chemaxon
pKa (Strongest Basic)-7.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area34.14 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity48.89 m3·mol-1Chemaxon
Polarizability17.84 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ba-0900000000-977b85d2f66fb318a4db
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-ddba2c838c050b3e0f49
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-2900000000-95a143f9792d9e670458
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00r2-7900000000-04c513494ac077a520f1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01dm-9300000000-7c8d3d66f7773d1f080a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-9400000000-005bc2ebaf635085e447
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]-140.9844102
predicted
DarkChem Lite v0.1.0
[M-H]-141.6936102
predicted
DarkChem Lite v0.1.0
[M-H]-141.2028102
predicted
DarkChem Lite v0.1.0
[M-H]-134.61276
predicted
DeepCCS 1.0 (2019)
[M+H]+141.4795102
predicted
DarkChem Lite v0.1.0
[M+H]+142.2827102
predicted
DarkChem Lite v0.1.0
[M+H]+142.0733102
predicted
DarkChem Lite v0.1.0
[M+H]+138.44011
predicted
DeepCCS 1.0 (2019)
[M+Na]+141.4639102
predicted
DarkChem Lite v0.1.0
[M+Na]+142.2544102
predicted
DarkChem Lite v0.1.0
[M+Na]+147.64471
predicted
DeepCCS 1.0 (2019)

Drug created at January 21, 2021 01:31 / Updated at January 24, 2021 06:04