Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 23:24:23 UTC
Update Date2022-09-22 18:34:26 UTC
HMDB IDHMDB0038122
Secondary Accession Numbers
  • HMDB38122
Metabolite Identification
Common NameCurcumol
Description5-Methyl-5-hexen-2-one, also known as 4-acetyl-2-methyl-1-butene or fema 3365, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. 5-Methyl-5-hexen-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Methyl-5-hexen-2-one is a foliage, green, and vegetable tasting compound. Outside of the human body,.
Structure
Data?1563863143
Synonyms
ValueSource
4-Acetyl-2-methyl-1-buteneHMDB
FEMA 3365HMDB
MethallylacetoneHMDB
5,8-Epoxy-10(14)-guaien-8-olHMDB
CurcumolMeSH
Chemical FormulaC15H24O2
Average Molecular Weight236.3499
Monoisotopic Molecular Weight236.177630012
IUPAC Name2-methyl-6-methylidene-9-(propan-2-yl)-11-oxatricyclo[6.2.1.0¹,⁵]undecan-8-ol
Traditional Name9-isopropyl-2-methyl-6-methylidene-11-oxatricyclo[6.2.1.0¹,⁵]undecan-8-ol
CAS Registry Number4871-97-0
SMILES
CC(C)C1CC23OC1(O)CC(=C)C2CCC3C
InChI Identifier
InChI=1S/C15H24O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h9,11-13,16H,3,5-8H2,1-2,4H3
InChI KeyQRMPRVXWPCLVNI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point141 - 142 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP2.63ALOGPS
logP3.07ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)11.75ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.92 m³·mol⁻¹ChemAxon
Polarizability27.59 ųChemAxon
Number of Rings3ChemAxon
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]+153.2131661259
DarkChem[M-H]-150.47131661259
DeepCCS[M-2H]-190.94730932474
DeepCCS[M+Na]+166.07530932474
AllCCS[M+H]+156.132859911
AllCCS[M+H-H2O]+152.432859911
AllCCS[M+NH4]+159.532859911
AllCCS[M+Na]+160.532859911
AllCCS[M-H]-163.032859911
AllCCS[M+Na-2H]-163.232859911
AllCCS[M+HCOO]-163.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CurcumolCC(C)C1CC23OC1(O)CC(=C)C2CCC3C2259.7Standard polar33892256
CurcumolCC(C)C1CC23OC1(O)CC(=C)C2CCC3C1650.6Standard non polar33892256
CurcumolCC(C)C1CC23OC1(O)CC(=C)C2CCC3C1713.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Curcumol,1TMS,isomer #1C=C1CC2(O[Si](C)(C)C)OC3(CC2C(C)C)C(C)CCC131730.0Semi standard non polar33892256
Curcumol,1TBDMS,isomer #1C=C1CC2(O[Si](C)(C)C(C)(C)C)OC3(CC2C(C)C)C(C)CCC131996.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Curcumol GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9430000000-e1674cb346da569a2fb62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Curcumol GC-MS (1 TMS) - 70eV, Positivesplash10-000l-9030000000-399b7159ca48b41b17f72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Curcumol 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 - Curcumol 10V, Positive-QTOFsplash10-000i-2090000000-873dc9ce8ca841c2c3852015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumol 20V, Positive-QTOFsplash10-05n0-9250000000-2aec5e80266e381c8d6f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumol 40V, Positive-QTOFsplash10-0a4i-9000000000-077b489b17b45ea88ce32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumol 10V, Negative-QTOFsplash10-000i-0090000000-d47490971e8b0274931d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumol 20V, Negative-QTOFsplash10-000i-0290000000-80d9c57bbfa557fabffe2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumol 40V, Negative-QTOFsplash10-066r-6910000000-3ba867119318826e533b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumol 10V, Negative-QTOFsplash10-000i-0090000000-c0031dc201eac6b6350a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumol 20V, Negative-QTOFsplash10-000i-0090000000-c0031dc201eac6b6350a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumol 40V, Negative-QTOFsplash10-00kr-0690000000-06dfb3057102cc0a96172021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumol 10V, Positive-QTOFsplash10-000i-0090000000-8472a524647920e2eae72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumol 20V, Positive-QTOFsplash10-000i-0090000000-a35b1ee8d04c470734022021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumol 40V, Positive-QTOFsplash10-0a4s-7950000000-d30c841ef7a06a60bed92021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008163
KNApSAcK IDNot Available
Chemspider ID198976
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound228604
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. Zhang W, Wang Z, Chen T: Curcumol induces apoptosis via caspases-independent mitochondrial pathway in human lung adenocarcinoma ASTC-a-1 cells. Med Oncol. 2011 Mar;28(1):307-14. doi: 10.1007/s12032-010-9431-5. Epub 2010 Feb 3. [PubMed:20127426 ]
  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.