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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:14:34 UTC
Update Date2022-03-07 02:55:09 UTC
HMDB IDHMDB0037000
Secondary Accession Numbers
  • HMDB37000
Metabolite Identification
Common Namealpha-Turmerone
Descriptionalpha-Turmerone, also known as α-turmerone, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on alpha-Turmerone.
Structure
Data?1563862962
Synonyms
ValueSource
a-TurmeroneGenerator
Α-turmeroneGenerator
2-Methyl-6-(4-methyl-2,4-cyclohexadien-1-yl)-2-hepten-4-ene, 9ciHMDB
(1'r,6S)-2-Methyl-6-(4-methylcyclohexa-2,4-dienyl)hept-2-en-4-oneMeSH, HMDB
alpha-TurmeroneMeSH
Chemical FormulaC15H22O
Average Molecular Weight218.3346
Monoisotopic Molecular Weight218.167065326
IUPAC Name2-methyl-6-(4-methylcyclohexa-2,4-dien-1-yl)hept-2-en-4-one
Traditional Name2-methyl-6-(4-methylcyclohexa-2,4-dien-1-yl)hept-2-en-4-one
CAS Registry Number82508-15-4
SMILES
CC(CC(=O)C=C(C)C)C1CC=C(C)C=C1
InChI Identifier
InChI=1S/C15H22O/c1-11(2)9-15(16)10-13(4)14-7-5-12(3)6-8-14/h5-7,9,13-14H,8,10H2,1-4H3
InChI KeyXOCANRBEOZQNAQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Bisabolane sesquiterpenoid
  • Sesquiterpenoid
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.047 g/LALOGPS
logP4.62ALOGPS
logP4.05ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.24 m³·mol⁻¹ChemAxon
Polarizability26.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+154.79831661259
DarkChem[M-H]-154.21531661259
DeepCCS[M+H]+157.98630932474
DeepCCS[M-H]-155.62930932474
DeepCCS[M-2H]-188.66130932474
DeepCCS[M+Na]+164.0830932474
AllCCS[M+H]+152.132859911
AllCCS[M+H-H2O]+148.232859911
AllCCS[M+NH4]+155.732859911
AllCCS[M+Na]+156.832859911
AllCCS[M-H]-158.932859911
AllCCS[M+Na-2H]-159.632859911
AllCCS[M+HCOO]-160.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-TurmeroneCC(CC(=O)C=C(C)C)C1CC=C(C)C=C12298.1Standard polar33892256
alpha-TurmeroneCC(CC(=O)C=C(C)C)C1CC=C(C)C=C11673.1Standard non polar33892256
alpha-TurmeroneCC(CC(=O)C=C(C)C)C1CC=C(C)C=C11659.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
alpha-Turmerone,1TMS,isomer #1CC(C)=CC(=CC(C)C1C=CC(C)=CC1)O[Si](C)(C)C1872.7Semi standard non polar33892256
alpha-Turmerone,1TMS,isomer #1CC(C)=CC(=CC(C)C1C=CC(C)=CC1)O[Si](C)(C)C1757.4Standard non polar33892256
alpha-Turmerone,1TBDMS,isomer #1CC(C)=CC(=CC(C)C1C=CC(C)=CC1)O[Si](C)(C)C(C)(C)C2085.3Semi standard non polar33892256
alpha-Turmerone,1TBDMS,isomer #1CC(C)=CC(=CC(C)C1C=CC(C)=CC1)O[Si](C)(C)C(C)(C)C2007.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Turmerone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9110000000-0719057b71d2427087012017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Turmerone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Turmerone 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 - alpha-Turmerone 10V, Positive-QTOFsplash10-014i-1390000000-42a2de594e130d4858cf2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Turmerone 20V, Positive-QTOFsplash10-00m0-8930000000-122b5ff283afad8039702015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Turmerone 40V, Positive-QTOFsplash10-1030-9300000000-d84d9e294494025768892015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Turmerone 10V, Negative-QTOFsplash10-014i-1190000000-60e30bb938450f3e76dc2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Turmerone 20V, Negative-QTOFsplash10-066r-9570000000-090591c1136c0965ddf22015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Turmerone 40V, Negative-QTOFsplash10-0a4i-9400000000-d366e8b20b7c3f2288652015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Turmerone 10V, Negative-QTOFsplash10-014i-0090000000-868e2fb00a2cfbf6c5292021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Turmerone 20V, Negative-QTOFsplash10-0159-4940000000-1579e12ec4d2ec2b6e9d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Turmerone 40V, Negative-QTOFsplash10-014i-9700000000-923d8b5c4b917f72744f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Turmerone 10V, Positive-QTOFsplash10-00di-6900000000-c27bbcc30ab609fee8132021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Turmerone 20V, Positive-QTOFsplash10-000x-9500000000-b9efb0b2450c6c097fe42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Turmerone 40V, Positive-QTOFsplash10-0006-9100000000-160460a0ad4f1daa47362021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB015975
KNApSAcK IDC00011639
Chemspider ID16737078
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14632996
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yue GG, Chan BC, Hon PM, Lee MY, Fung KP, Leung PC, Lau CB: Evaluation of in vitro anti-proliferative and immunomodulatory activities of compounds isolated from Curcuma longa. Food Chem Toxicol. 2010 Aug-Sep;48(8-9):2011-20. doi: 10.1016/j.fct.2010.04.039. Epub 2010 May 9. [PubMed:20438793 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.