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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:55:52 UTC
Update Date2020-04-03 19:27:24 UTC
HMDB IDHMDB0061851
Secondary Accession Numbers
  • HMDB61851
Metabolite Identification
Common Namealpha-Copaene
Descriptionalpha-Copaene, also known as aglaiene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. alpha-Copaene is possibly neutral. alpha-Copaene is a spice and woody tasting compound that can be found in several food items such as lime, mandarin orange (clementine, tangerine), safflower, and summer savoury, which makes alpha-copaene a potential biomarker for the consumption of these food products. alpha-Copaene can be found in feces and saliva.
Structure
Data?1585942043
Synonyms
ValueSource
(-)-CopaeneHMDB
(-)-alpha-CopaeneHMDB
(-)-α-CopaeneHMDB
(1R,2S,6S,7S,8S)-(-)-8-Isopropyl-1,3-dimethyltricyclo[4.4.0.02,7]dec-3-eneHMDB
(1R,2S,6S,7S,8S)-1,3-Dimethyl-8-(1-methylethyl)tricyclo[4.4.0.02,7]dec-3-eneHMDB
AglaieneHMDB
CopaeneHMDB
alpha-CopaeneHMDB
α-CopaeneHMDB
Chemical FormulaC15H24
Average Molecular Weight204.357
Monoisotopic Molecular Weight204.187800773
IUPAC Name(1R,2S,6S,7S,8S)-1,3-dimethyl-8-(propan-2-yl)tricyclo[4.4.0.0^{2,7}]dec-3-ene
Traditional Name(1R,2S,6S,7S,8S)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0^{2,7}]dec-3-ene
CAS Registry Number3856-25-5
SMILES
CC(C)[C@@H]1CC[C@]2(C)[C@H]3CC=C(C)[C@@H]2[C@@H]13
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-BTFPBAQTSA-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
  • 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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring 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
Polarizability26.17 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Diarrhoea predominant irritable bowel syndrome
  1. Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Crohn's disease
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Ulcerative colitis
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001522
KNApSAcK IDC00003118
Chemspider ID10231594
KEGG Compound IDC09639
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCopaene
METLIN IDNot Available
PubChem Compound12303902
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  10. Wikipedia [Link]
  11. UniProt B9S9Z3 : Alpha-copaene synthase [Link]
  12. UniProt Q4U3F6 : Alpha-copaene synthase [Link]