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Record Information
Version4.0
Creation Date2014-10-08 15:55:52 UTC
Update Date2017-09-27 08:44:15 UTC
HMDB IDHMDB0061851
Secondary Accession Numbers
  • HMDB61851
Metabolite Identification
Common Namealpha-Copaene
Descriptionalpha-Copaene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
Structure
Thumb
Synonyms
ValueSource
(1S,6S,7S,8S)-8-Isopropyl-1,3-dimethyltricyclo[4.4.0.0(2,7)]dec-3-eneChEBI
8-Isopropyl-1,3-dimethyltricyclo(4.4.0.02,7)dec-3-eneChEBI
CopaeneChEBI
a-CopaeneGenerator
α-copaeneGenerator
Chemical FormulaC15H24
Average Molecular Weight204.357
Monoisotopic Molecular Weight204.187800773
IUPAC Name(1S,6S,7S,8S)-1,3-dimethyl-8-(propan-2-yl)tricyclo[4.4.0.0²,⁷]dec-3-ene
Traditional Name(1S,6S,7S,8S)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene
CAS Registry Number3856-25-5
SMILES
[H][C@@]12C3C(C)=CC[C@]1([H])[C@]3(C)CC[C@H]2C(C)C
InChI Identifier
InChI=1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)14(15)13(11)12/h5,9,11-14H,6-8H2,1-4H3/t11-,12-,13-,14?,15-/m0/s1
InChI KeyVLXDPFLIRFYIME-XIQJJJERSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Copaane sesquiterpenoid
  • Sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0018 g/LALOGPS
logP3.75ALOGPS
logP4.09ChemAxon
logS-5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity65.77 m³·mol⁻¹ChemAxon
Polarizability0 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-6910000000-819571f4000f4ce2f677View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0190000000-a9c75307ad9fa7e5726bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0390000000-12dc458834cb96e2536dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059i-0920000000-4d0945c6547417b0848dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-5fefaad65bd188e67a4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-2342a92a86b61876ef46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-0950000000-518835a78468ff13b3a1View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Feces
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Children (1-13 years old)BothNormal details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothCrohns disease details
FecesDetected but not Quantified Adult (>18 years old)BothUlcerative colitis details
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not Quantified Adult (>18 years old)Both
Diarrhea-predominant IBS
details
FecesDetected but not Quantified Children (1-13 years old)BothAutism details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001522
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-8234
BiGG IDNot Available
Wikipedia LinkCopaene
METLIN IDNot Available
PubChem Compound70678558
PDB IDNot Available
ChEBI ID10221
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Schreier P, Drawert F, Junker A: [Sesquiterpene hydrocarbons from grapes (author's transl)]. Z Lebensm Unters Forsch. 1976;160(3):271-4. [PubMed:983335 ]
  2. Senatore F, Arnold NA, Piozzi F: Chemical composition of the essential oil of Salvia multicaulis Vahl. var. simplicifolia Boiss. growing wild in Lebanon. J Chromatogr A. 2004 Oct 15;1052(1-2):237-40. [PubMed:15527145 ]
  3. Estell RE, Fredrickson EL, Anderson DM, Remmenga MD: Effects of gamma-terpinene, terpinolene, alpha-copaene, and alpha-terpinene on consumption of alfalfa pellets by sheep. J Anim Sci. 2005 Aug;83(8):1967-71. [PubMed:16024718 ]
  4. Chaverri C, Ciccio JF: Essential oil of trees of the genus Ocotea (Lauraceae) in Costa Rica. I. Ocotea brenesii. Rev Biol Trop. 2005 Sep-Dec;53(3-4):431-6. [PubMed:17354452 ]
  5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. Wikipedia [Link]
  10. UniProt B9S9Z3 : Alpha-copaene synthase [Link]
  11. UniProt Q4U3F6 : Alpha-copaene synthase [Link]