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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:38:04 UTC
Update Date2019-07-23 06:16:50 UTC
HMDB IDHMDB0034732
Secondary Accession Numbers
  • HMDB34732
Metabolite Identification
Common NameThymoquinone
DescriptionThymoquinone, also known as thymoil, belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively. It has been classified as a pan-assay interference compound, which binds indiscriminately to many proteins. Thymoquinone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Thymoquinone is found, on average, in the highest concentration within winter savories. Thymoquinone has also been detected, but not quantified in, herbs and spices. This could make thymoquinone a potential biomarker for the consumption of these foods. Thymoquinone is a phytochemical compound found in the plant Nigella sativa. In laboratory experiments in cells and in animals, it has shown antiinflammatory and antioxidant effects, and has been studied in models of cardiovascular diseases and diabetes, neurodegenerative diseases and stroke, and cancer. It is also found in select cultivated Monarda fistulosa plants grown in the U.S. and steam distilled producing an essential oil. A 2016 study suggests thymoquinone may have opioid tolerance-reduction effects.
Structure
Data?1563862610
Synonyms
ValueSource
2-Isopropyl-5-methyl-1,4-benzoquinoneHMDB
2-Isopropyl-5-methyl-p-benzoquinoneHMDB
2-Isopropyl-5-methylbenzo-1,4-quinoneHMDB
2-Isopropyl-5-methylbenzoquinoneHMDB
2-Methyl-5-(1-methylethyl)-2,5-cyclohexadiene-1,4-dioneHMDB
2-Methyl-5-(1-methylethyl)-2,5-cyclohexadiene-1,4-dione, 9ciHMDB
2-Methyl-5-isopropyl-1,4-benzoquinoneHMDB
2-Methyl-5-isopropyl-p-benzoquinoneHMDB
5-Isopropyl-2-methyl-1,4-benzoquinoneHMDB
5-Isopropyl-2-methyl-2,5-cyclohexadiene-1,4-dioneHMDB
5-Isopropyl-2-methyl-p-benzoquinoneHMDB
p-Cymene-2,5-dioneHMDB
p-Mentha-3,6-diene-2,5-dione (8ci)HMDB
PolythymoquinoneHMDB
ThymoilHMDB
ThymolquinoneHMDB
ThymoquinonHMDB
DihydrothymoquinoneHMDB
ThymoquinoneMeSH
Chemical FormulaC10H12O2
Average Molecular Weight164.2011
Monoisotopic Molecular Weight164.083729628
IUPAC Name2-methyl-5-(propan-2-yl)cyclohexa-2,5-diene-1,4-dione
Traditional Namethymoquinone
CAS Registry Number490-91-5
SMILES
CC(C)C1=CC(=O)C(C)=CC1=O
InChI Identifier
InChI=1S/C10H12O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h4-6H,1-3H3
InChI KeyKEQHJBNSCLWCAE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentP-benzoquinones
Alternative Parents
Substituents
  • P-benzoquinone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point44 - 45 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.20Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.83 g/LALOGPS
logP2ALOGPS
logP2.55ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)-7.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.89 m³·mol⁻¹ChemAxon
Polarizability17.84 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xr-6900000000-764f3b8a1150b1cac052Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-96f0c8e4e4f4a8455abeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-5900000000-441064ba80ff42a70cfeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9200000000-c6d527c2a9a79f901029Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-d9e63c8d82efebaf41b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-98b2dccaab2bbdb236feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-9500000000-19dae31b3a18d5f7735cSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013274
KNApSAcK IDC00010876
Chemspider ID9861
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThymoquinone
METLIN IDNot Available
PubChem Compound10281
PDB IDIMW
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Reindl W, Yuan J, Kramer A, Strebhardt K, Berg T: Inhibition of polo-like kinase 1 by blocking polo-box domain-dependent protein-protein interactions. Chem Biol. 2008 May;15(5):459-66. doi: 10.1016/j.chembiol.2008.03.013. [PubMed:18482698 ]
  2. Fararh KM, Shimizu Y, Shiina T, Nikami H, Ghanem MM, Takewaki T: Thymoquinone reduces hepatic glucose production in diabetic hamsters. Res Vet Sci. 2005 Dec;79(3):219-23. Epub 2005 Apr 1. [PubMed:16054891 ]
  3. Abdel-Fattah AM, Matsumoto K, Watanabe H: Antinociceptive effects of Nigella sativa oil and its major component, thymoquinone, in mice. Eur J Pharmacol. 2000 Jul 14;400(1):89-97. [PubMed:10913589 ]
  4. Hosseinzadeh H, Parvardeh S: Anticonvulsant effects of thymoquinone, the major constituent of Nigella sativa seeds, in mice. Phytomedicine. 2004 Jan;11(1):56-64. [PubMed:14971722 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .