Showing Compound Card for alpha-Copaene (CDB000063)

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Record Information
Version1.0
Created at2020-03-18 23:23:25 UTC
Updated at2020-11-18 16:34:43 UTC
CannabisDB IDCDB000063
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namealpha-Copaene
DescriptionAlpha-copaene is formally classified as a homocyclic organic compound although it is biochemically a sesquiterpenoid synthesized from isoprene units. Alpha-copaene is an oily liquid hydrocarbon that is found in a number of essential oil-producing plants and whose name is derived from the resin-producing tropical copaiba tree. Alpha-copaene was detected in the essential oils from the inner bark of the plant Kielmeyera coriacea Mart. & Zucc. (PMID: 25960759 ), the bark from Annona reticulate (PMID: 22007723 ) and was found in the leaves of Cedrelopsis grevei (PMID: 23459148 ), and Xylopia laevigata (PMID: 23307235 ). It is found in traces amount in cannabis plants (PMID: 6991645 ). Alpha-copaene is a colorless clear viscous liquid with a spicy and woody taste. It 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. Copaene has been found to increase the antioxidant capacity in human lymphocytes in vitro (PMID: 24287609 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
a-CopaeneGenerator
Α-copaeneGenerator
(-)-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-CopaneneHMDB
Α-copaneneHMDB
alpha-CopaeneHMDB
Chemical FormulaC15H24
Average Molecular Weight204.36
Monoisotopic Molecular Weight204.1878
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)C2[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-XIQJJJERSA-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
Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-c084f3d998cc56a199d62021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-3c4675614578d86c565d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0btd-6920000000-b4a877b11b4c0fff34602021-09-23View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.05 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0061851
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. Martins Cde M, do Nascimento EA, de Morais SA, de Oliveira A, Chang R, Cunha LC, Martins MM, Martins CH, Moraes Tda S, Rodrigues PV, da Silva CV, de Aquino FJ: Chemical Constituents and Evaluation of Antimicrobial and Cytotoxic Activities of Kielmeyera coriacea Mart. & Zucc. Essential Oils. Evid Based Complement Alternat Med. 2015;2015:842047. doi: 10.1155/2015/842047. Epub 2015 Apr 16. [PubMed:25960759 ]
  2. Afoulous S, Ferhout H, Raoelison EG, Valentin A, Moukarzel B, Couderc F, Bouajila J: Chemical composition and anticancer, antiinflammatory, antioxidant and antimalarial activities of leaves essential oil of Cedrelopsis grevei. Food Chem Toxicol. 2013 Jun;56:352-62. doi: 10.1016/j.fct.2013.02.008. Epub 2013 Feb 28. [PubMed:23459148 ]
  3. Quintans Jde S, Soares BM, Ferraz RP, Oliveira AC, da Silva TB, Menezes LR, Sampaio MF, Prata AP, Moraes MO, Pessoa C, Antoniolli AR, Costa EV, Bezerra DP: Chemical constituents and anticancer effects of the essential oil from leaves of Xylopia laevigata. Planta Med. 2013 Jan;79(2):123-30. doi: 10.1055/s-0032-1328091. Epub 2013 Jan 10. [PubMed:23307235 ]
  4. Chavan MJ, Wakte PS, Shinde DB: Analgesic and anti-inflammatory activities of the sesquiterpene fraction from Annona reticulata L. bark. Nat Prod Res. 2012;26(16):1515-8. doi: 10.1080/14786419.2011.564583. Epub 2011 Oct 19. [PubMed:22007723 ]
  5. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  6. Turkez H, Celik K, Togar B: Effects of copaene, a tricyclic sesquiterpene, on human lymphocytes cells in vitro. Cytotechnology. 2014 Aug;66(4):597-603. doi: 10.1007/s10616-013-9611-1. Epub 2013 Nov 28. [PubMed:24287609 ]