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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:55:36 UTC
Update Date2022-03-07 03:17:47 UTC
HMDB IDHMDB0061838
Secondary Accession Numbers
  • HMDB61838
Metabolite Identification
Common Name(-)-alpha-Curcumene
Description(-)-alpha-Curcumene, also known as (R)-curcumene or L-α-curcumene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units (-)-alpha-Curcumene is possibly neutral.
Structure
Data?1563866237
Synonyms
ValueSource
(R)-(-)-alpha-CurcumeneChEBI
(R)-(-)-CurcumeneChEBI
(R)-CurcumeneChEBI
4-[(1R)-1,5-Dimethylhex-4-enyl]-1-methylbenzeneChEBI
L-alpha-CurcumeneChEBI
(R)-1-(1,5-Dimethyl-4-hexenyl)-4-methylbenzeneKegg
(R)-(-)-a-CurcumeneGenerator
(R)-(-)-Α-curcumeneGenerator
L-a-CurcumeneGenerator
L-Α-curcumeneGenerator
(-)-a-CurcumeneGenerator
(-)-Α-curcumeneGenerator
(R)-Isomer OF alpha-curcumeneHMDB
1-(1,5-Dimethyl-4-hexenyl)-4-methylbenzeneHMDB
2-Methyl-6-p-tolyl-2-hepteneHMDB
alpha-CurcumeneHMDB
(S)-Isomer OF alpha-curcumeneHMDB
Ar-curcumeneHMDB
Chemical FormulaC15H22
Average Molecular Weight202.3352
Monoisotopic Molecular Weight202.172150704
IUPAC Name1-methyl-4-[(2R)-6-methylhept-5-en-2-yl]benzene
Traditional Name(-)-α-curcumene
CAS Registry Number4176-17-4
SMILES
[H][C@@](C)(CCC=C(C)C)C1=CC=C(C)C=C1
InChI Identifier
InChI=1S/C15H22/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-11,14H,5,7H2,1-4H3/t14-/m1/s1
InChI KeyVMYXUZSZMNBRCN-CQSZACIVSA-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
  • P-cymene
  • Toluene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aromatic hydrocarbon
  • Branched unsaturated hydrocarbon
  • Cyclic olefin
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

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 Solubility0.00099 g/LALOGPS
logP6.15ALOGPS
logP5.39ChemAxon
logS-5.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity69.09 m³·mol⁻¹ChemAxon
Polarizability25.82 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+150.62931661259
DarkChem[M-H]-149.90731661259
DeepCCS[M+H]+160.33130932474
DeepCCS[M-H]-157.93530932474
DeepCCS[M-2H]-191.1630932474
DeepCCS[M+Na]+166.24330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(-)-alpha-Curcumene[H][C@@](C)(CCC=C(C)C)C1=CC=C(C)C=C11925.6Standard polar33892256
(-)-alpha-Curcumene[H][C@@](C)(CCC=C(C)C)C1=CC=C(C)C=C11487.0Standard non polar33892256
(-)-alpha-Curcumene[H][C@@](C)(CCC=C(C)C)C1=CC=C(C)C=C11498.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (-)-alpha-Curcumene GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-4900000000-75e61317c346feecec2e2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-alpha-Curcumene 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-Curcumene 10V, Positive-QTOFsplash10-0udi-0290000000-9e5665300d38ccc6c3802017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 20V, Positive-QTOFsplash10-100r-9840000000-d684318a257bbd05693f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 40V, Positive-QTOFsplash10-066r-9400000000-671ed7e91a8152a3dedd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 10V, Negative-QTOFsplash10-0udi-0090000000-49907b25f88bc4223ff52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 20V, Negative-QTOFsplash10-0udi-0090000000-78accdf5fb04e051742c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 40V, Negative-QTOFsplash10-0ldr-3910000000-0e04f561e347dce60ba22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 10V, Positive-QTOFsplash10-014l-7910000000-070594523adb5fcf25902021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 20V, Positive-QTOFsplash10-00kf-9300000000-875e64f2a9577f75db092021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 40V, Positive-QTOFsplash10-0006-9400000000-8fa08e9b4d33a2cfb93e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 10V, Negative-QTOFsplash10-0udi-0090000000-0b1ac00c3b3c6c0a73b92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 20V, Negative-QTOFsplash10-0udi-0290000000-a1f573a51214364e1f182021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 40V, Negative-QTOFsplash10-0007-6900000000-b097197b38fa1f21c6f12021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001674
KNApSAcK IDC00011617
Chemspider IDNot Available
KEGG Compound IDC09649
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442360
PDB IDNot Available
ChEBI ID10225
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. Lenfeld J, Motl O, Trka A: Anti-inflammatory activity of extracts from Conyza canadensis. Pharmazie. 1986 Apr;41(4):268-9. [PubMed:3725873 ]
  2. D'Armas HT, Mootoo BS, Reynolds WF: An unusual sesquiterpene derivative from the Caribbean gorgonian Pseudopterogorgia rigida. J Nat Prod. 2000 Nov;63(11):1593-5. [PubMed:11087620 ]
  3. Schwob I, Bessiere JM, Dherbomez M, Viano J: Composition and antimicrobial activity of the essential oil of Hypericum coris. Fitoterapia. 2002 Oct;73(6):511-3. [PubMed:12385876 ]
  4. Antonious GF, Kochhar TS: Zingiberene and curcumene in wild tomato. J Environ Sci Health B. 2003 Jul;38(4):489-500. [PubMed:12856930 ]
  5. Zhang A, RajanBabu TV: Chiral benzyl centers through asymmetric catalysis. a three-step synthesis of (R)-(-)-alpha-curcumene via asymmetric hydrovinylation. Org Lett. 2004 Sep 2;6(18):3159-61. [PubMed:15330612 ]
  6. Takigawa H, Kubota H, Sonohara H, Okuda M, Tanaka S, Fujikura Y, Ito S: Novel Allylic Oxidation of alpha-Cedrene to sec-Cedrenol by a Rhodococcus Strain. Appl Environ Microbiol. 1993 May;59(5):1336-41. [PubMed:16348930 ]
  7. Mathela CS, Padalia RC, Chanotiya CS: Kanokonyl acetate-rich Indian valerian from northwestern Himalaya. Nat Prod Commun. 2009 Sep;4(9):1253-6. [PubMed:19831039 ]
  8. Takigawa H, Sugiyama M, Shibuya Y: C(35)-terpenes from Bacillus subtilis KSM 6-10. J Nat Prod. 2010 Feb 26;73(2):204-7. doi: 10.1021/np900705q. [PubMed:20085287 ]
  9. Joshi RK: Chemical composition of the essential oil of Lepidagathis fasciculata from Bondla forest of Goa, India. Nat Prod Commun. 2013 Aug;8(8):1163-4. [PubMed:24079194 ]
  10. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.