Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-03-07 21:34:33 UTC
Update Date2022-03-07 03:17:37 UTC
HMDB IDHMDB0059878
Secondary Accession Numbers
  • HMDB59878
Metabolite Identification
Common Namealpha-Curcumene
Descriptionalpha-Curcumene, also known as ar-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?1563865986
Synonyms
ValueSource
1-(1,5-Dimethyl-4-hexenyl)-4-methylbenzeneChEBI
2-Methyl-6-p-tolyl-2-hepteneChEBI
Ar-curcumeneChEBI
Aromatic curcumeneChEBI
Aryl-curcumeneChEBI
CurcumeneChEBI
a-CurcumeneGenerator
Α-curcumeneGenerator
(S)-Isomer OF alpha-curcumeneHMDB
(R)-Isomer OF alpha-curcumeneHMDB
Chemical FormulaC15H22
Average Molecular Weight202.341
Monoisotopic Molecular Weight202.172150708
IUPAC Name1-methyl-4-(6-methylhept-5-en-2-yl)benzene
Traditional Namecurcumene
CAS Registry NumberNot Available
SMILES
CC(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
InChI KeyVMYXUZSZMNBRCN-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
  • 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
Not AvailableNot Available
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
Polarizability26.17 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]+151.02131661259
DarkChem[M-H]-147.64831661259
DeepCCS[M+H]+153.3330932474
DeepCCS[M-H]-150.97230932474
DeepCCS[M-2H]-185.81630932474
DeepCCS[M+Na]+160.830932474
AllCCS[M+H]+146.332859911
AllCCS[M+H-H2O]+142.232859911
AllCCS[M+NH4]+150.132859911
AllCCS[M+Na]+151.232859911
AllCCS[M-H]-152.232859911
AllCCS[M+Na-2H]-152.732859911
AllCCS[M+HCOO]-153.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-CurcumeneCC(CCC=C(C)C)C1=CC=C(C)C=C11889.7Standard polar33892256
alpha-CurcumeneCC(CCC=C(C)C)C1=CC=C(C)C=C11471.5Standard non polar33892256
alpha-CurcumeneCC(CCC=C(C)C)C1=CC=C(C)C=C11466.5Semi 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-4900000000-02de9aa588ac8b9539322016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Curcumene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Curcumene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-067l-6900000000-5adc5ed56d3450aebc612015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Curcumene 10V, Positive-QTOFsplash10-0udi-1390000000-266c956bab292ff3d48f2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Curcumene 20V, Positive-QTOFsplash10-0uyi-5940000000-13708122d7e2946ab5892016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Curcumene 40V, Positive-QTOFsplash10-014i-9600000000-8069c29cdaa20b53c0572016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Curcumene 10V, Negative-QTOFsplash10-0udi-0090000000-705074079b3b227e81792016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Curcumene 20V, Negative-QTOFsplash10-0udi-0190000000-189af3990d1c9d3163cc2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Curcumene 40V, Negative-QTOFsplash10-0ldr-4910000000-7bf2915fe0383c8edf0d2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Curcumene 10V, Positive-QTOFsplash10-014l-8910000000-59d05b6be264b168f53f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Curcumene 20V, Positive-QTOFsplash10-00kf-9300000000-d00dad7d95d26e8476aa2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Curcumene 40V, Positive-QTOFsplash10-00kf-9400000000-fea80cf888f289c0c3632021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Curcumene 10V, Negative-QTOFsplash10-0udi-0090000000-0b1ac00c3b3c6c0a73b92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Curcumene 20V, Negative-QTOFsplash10-0udi-0290000000-77743b81a0809cd739782021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Curcumene 40V, Negative-QTOFsplash10-00kf-9700000000-dcc11611bd47e375b87a2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-11391
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92139
PDB IDNot Available
ChEBI ID62757
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. Haider SZ, Andola HC, Mohan M: Constituents of Artemisia gmelinii Weber ex Stechm. from Uttarakhand Himalaya: A Source of Artemisia Ketone. Indian J Pharm Sci. 2012 May;74(3):265-7. doi: 10.4103/0250-474X.106074. [PubMed:23439844 ]
  2. Sato T, Hoshino H, Yoshida S, Nakajima M, Hoshino T: Bifunctional triterpene/sesquarterpene cyclase: tetraprenyl-beta-curcumene cyclase is also squalene cyclase in Bacillus megaterium. J Am Chem Soc. 2011 Nov 9;133(44):17540-3. doi: 10.1021/ja2060319. Epub 2011 Oct 13. [PubMed:21981578 ]
  3. Afoulous S, Ferhout H, Raoelison EG, Valentin A, Moukarzel B, Couderc F, Bouajila J: Helichrysum gymnocephalum essential oil: chemical composition and cytotoxic, antimalarial and antioxidant activities, attribution of the activity origin by correlations. Molecules. 2011 Sep 29;16(10):8273-91. doi: 10.3390/molecules16108273. [PubMed:21959299 ]
  4. Chu SS, Liu ZL, Du SS, Deng ZW: Chemical composition and insecticidal activity against Sitophilus zeamais of the essential oils derived from Artemisia giraldii and Artemisia subdigitata. Molecules. 2012 Jun 13;17(6):7255-65. doi: 10.3390/molecules17067255. [PubMed:22695231 ]
  5. Du ZT, Zheng S, Chen G, Lv D: A short synthesis of bisabolane sesquiterpenes. Molecules. 2011 Sep 19;16(9):8053-61. doi: 10.3390/molecules16098053. [PubMed:21931286 ]
  6. Sato T, Yoshida S, Hoshino H, Tanno M, Nakajima M, Hoshino T: Sesquarterpenes (C35 terpenes) biosynthesized via the cyclization of a linear C35 isoprenoid by a tetraprenyl-beta-curcumene synthase and a tetraprenyl-beta-curcumene cyclase: identification of a new terpene cyclase. J Am Chem Soc. 2011 Jun 29;133(25):9734-7. doi: 10.1021/ja203779h. Epub 2011 Jun 7. [PubMed:21627333 ]
  7. Podlogar JA, Verspohl EJ: Antiinflammatory effects of ginger and some of its components in human bronchial epithelial (BEAS-2B) cells. Phytother Res. 2012 Mar;26(3):333-6. doi: 10.1002/ptr.3558. Epub 2011 Jun 23. [PubMed:21698672 ]
  8. Caroprese Araque JF, Parra Garces MI, Arrieta Prieto D, Stashenko E: [Microscopic anatomy and volatile secondary metabolites at three stages of development of the inflorescences of Lantana camara (Verbenaceae)]. Rev Biol Trop. 2011 Mar;59(1):473-86. [PubMed:21516661 ]
  9. Weston RJ, Smith GJ: Sesquiterpenes from the inner bark of the silver birch and the paper birch. Nat Prod Commun. 2012 Feb;7(2):145-8. [PubMed:22474938 ]
  10. Bleeker PM, Diergaarde PJ, Ament K, Schutz S, Johne B, Dijkink J, Hiemstra H, de Gelder R, de Both MT, Sabelis MW, Haring MA, Schuurink RC: Tomato-produced 7-epizingiberene and R-curcumene act as repellents to whiteflies. Phytochemistry. 2011 Jan;72(1):68-73. doi: 10.1016/j.phytochem.2010.10.014. Epub 2010 Nov 11. [PubMed:21074818 ]
  11. Liu ZL, He Q, Chu SS, Wang CF, Du SS, Deng ZW: Essential oil composition and larvicidal activity of Saussurea lappa roots against the mosquito Aedes albopictus (Diptera: Culicidae). Parasitol Res. 2012 Jun;110(6):2125-30. doi: 10.1007/s00436-011-2738-0. Epub 2011 Dec 14. [PubMed:22167373 ]
  12. Lin J, Dou J, Xu J, Aisa HA: Chemical composition, antimicrobial and antitumor activities of the essential oils and crude extracts of Euphorbia macrorrhiza. Molecules. 2012 May 3;17(5):5030-9. doi: 10.3390/molecules17055030. [PubMed:22555293 ]
  13. Afewerki S, Breistein P, Pirttila K, Deiana L, Dziedzic P, Ibrahem I, Cordova A: Catalytic enantioselective beta-alkylation of alpha,beta-unsaturated aldehydes by combination of transition-metal- and aminocatalysis: total synthesis of bisabolane sesquiterpenes. Chemistry. 2011 Aug 1;17(32):8784-8. doi: 10.1002/chem.201100756. Epub 2011 Jul 5. [PubMed:21732445 ]
  14. Fujiwara M, Marumoto S, Yagi N, Miyazawa M: Biotransformation of turmerones by Aspergillus niger. J Nat Prod. 2011 Jan 28;74(1):86-9. doi: 10.1021/np100416v. Epub 2010 Dec 28. [PubMed:21189039 ]
  15. Ali NA, Wursterb M, Denkert A, Arnold N, Fadail I, Al-Didamony G, Lindequist U, Wessjohann L, Setzer WN: Chemical composition, antimicrobial, antioxidant and cytotoxic activity of essential oils of Plectranthus cylindraceus and Meriandra benghalensis from Yemen. Nat Prod Commun. 2012 Aug;7(8):1099-102. [PubMed:22978239 ]
  16. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  17. 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 ]
  18. 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 ]
  19. 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 ]
  20. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.