Thymoquinone (CHEM028748)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:40:07 UTC
Update Date2016-11-09 01:18:45 UTC
Accession NumberCHEM028748
Identification
Common NameThymoquinone
ClassSmall Molecule
DescriptionA member of the class of 1,4-benzoquinones that is 1,4-bezoquinone in which the hydrogens at positions 2 and 5 are replaced by methyl and isopropyl groups, respectively. It is a natural compound isolated from Nigella sativa which has demonstrated promising chemotherapeutic activity.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass164.201 g/mol
Monoisotopic Mass164.084 g/mol
CAS Registry Number490-91-5
IUPAC Name2-methyl-5-(propan-2-yl)cyclohexa-2,5-diene-1,4-dione
Traditional Namethymoquinone
SMILESCC(C)C1=CC(=O)C(C)=CC1=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xr-6900000000-764f3b8a1150b1cac052Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-8db47caa9667c101bd0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-5a485fdf30f3fb6eef66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9500000000-e6c8bd2fffd875c29cffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-7a4cd3c2c5dcf8576412Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xr-3900000000-c1e3ac1b0edf80cd5e27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9100000000-897472ebb650188b991dSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0034732
FooDB IDFDB013274
Phenol Explorer IDNot Available
KNApSAcK IDC00010876
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDIMW
Wikipedia LinkThymoquinone
Chemspider ID9861
ChEBI ID113532
PubChem Compound ID10281
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23135290
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=29519737
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=30422744
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=32074066
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=32133061
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=32560283
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=32588453
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=32596711
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=32608003
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=32610056
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=32618005
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=32620860
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=32637881
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=32652915
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=32767958
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=32774669
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=32774804
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=32793594
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=32843585
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=32860490
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=32867015
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=32901987
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=32920292
24. 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.
25. 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.
26. 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.
27. Hosseinzadeh H, Parvardeh S: Anticonvulsant effects of thymoquinone, the major constituent of Nigella sativa seeds, in mice. Phytomedicine. 2004 Jan;11(1):56-64.
28. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.