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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:38:04 UTC
Update Date2021-10-13 06:43:22 UTC
HMDB IDHMDB0034732
Secondary Accession Numbers
  • HMDB34732
Metabolite Identification
Common NameThymoquinone
DescriptionThymoquinone, also known as TQ, 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. Thymoquinone is found, on average, in the highest concentration within winter savories (Satureja montana). 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 secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Thymoquinone.
Structure
Data?1563862610
Synonyms
ValueSource
2-Isopropyl-5-methyl-1,4-benzoquinoneChEBI
2-Isopropyl-5-methyl-p-benzoquinoneChEBI
2-Methyl-5-(1-methylethyl)-2,5-cyclohexadiene-1,4-dioneChEBI
5-Isopropyl-2-methyl-2,5-cyclohexadiene-1,4-dioneChEBI
p-Cymene-2,5-dioneChEBI
p-Mentha-3,6-diene-2,5-dioneChEBI
ThymoquinonChEBI
TQChEBI
2-Isopropyl-5-methylbenzo-1,4-quinoneHMDB
2-Isopropyl-5-methylbenzoquinoneHMDB, MeSH
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, MeSH
5-Isopropyl-2-methyl-1,4-benzoquinoneHMDB
5-Isopropyl-2-methyl-P-benzoquinoneHMDB
P-Mentha-3,6-diene-2,5-dione (8ci)HMDB
PolythymoquinoneHMDB
ThymoilHMDB
ThymolquinoneHMDB
DihydrothymoquinoneMeSH, HMDB
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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point44 - 45 °CNot Available
Boiling Point230.00 to 232.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility865.3 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.20Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.83 g/LALOGPS
logP10(2) g/LALOGPS
logP10(2.55) g/LChemAxon
logS10(-2) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.21631661259
DarkChem[M-H]-132.77331661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Thymoquinone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xr-6900000000-764f3b8a1150b1cac0522017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thymoquinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thymoquinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thymoquinone 10V, Positive-QTOFsplash10-014i-0900000000-96f0c8e4e4f4a8455abe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thymoquinone 20V, Positive-QTOFsplash10-014i-5900000000-441064ba80ff42a70cfe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thymoquinone 40V, Positive-QTOFsplash10-014i-9200000000-c6d527c2a9a79f9010292016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thymoquinone 10V, Negative-QTOFsplash10-03di-0900000000-d9e63c8d82efebaf41b12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thymoquinone 20V, Negative-QTOFsplash10-03di-0900000000-98b2dccaab2bbdb236fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thymoquinone 40V, Negative-QTOFsplash10-014r-9500000000-19dae31b3a18d5f7735c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thymoquinone 10V, Negative-QTOFsplash10-03di-0900000000-8db47caa9667c101bd0f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thymoquinone 20V, Negative-QTOFsplash10-03di-0900000000-5a485fdf30f3fb6eef662021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thymoquinone 40V, Negative-QTOFsplash10-014i-9500000000-e6c8bd2fffd875c29cff2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thymoquinone 10V, Positive-QTOFsplash10-014i-0900000000-7a4cd3c2c5dcf85764122021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thymoquinone 20V, Positive-QTOFsplash10-00xr-3900000000-c1e3ac1b0edf80cd5e272021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thymoquinone 40V, Positive-QTOFsplash10-00kf-9100000000-897472ebb650188b991d2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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 ID113532
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1289381
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.. .