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
1-(Phenylamino)-8-naphthalenesulfonic acidChEBI
1-ANILINO-8-naphthalene sulfonATEChEBI
1-Anilino-8-naphthalenesulfonateChEBI
1-Anilino-8-naphthalenesulfonic acidChEBI
8-Anilino-1-naphthalene sulfonic acidChEBI
8-Anilinonaphthalene-1-sulphonic acidChEBI
ANSChEBI
1-(Phenylamino)-8-naphthalenesulfonateGenerator
1-(Phenylamino)-8-naphthalenesulphonateGenerator
1-(Phenylamino)-8-naphthalenesulphonic acidGenerator
1-ANILINO-8-naphthalene sulfonic acidGenerator
1-ANILINO-8-naphthalene sulphonateGenerator
1-ANILINO-8-naphthalene sulphonic acidGenerator
1-Anilino-8-naphthalenesulphonateGenerator
1-Anilino-8-naphthalenesulphonic acidGenerator
8-Anilino-1-naphthalene sulphonateGenerator
8-Anilino-1-naphthalene sulphonic acidGenerator
8-Anilinonaphthalene-1-sulfonateGenerator
8-Anilinonaphthalene-1-sulfonic acidGenerator
8-Anilinonaphthalene-1-sulphonateGenerator
1-Anilino-8-naphthalenesulfonate, monoammonium salt, hemihydrateHMDB
1-Anilino-8-naphthalenesulfonate, monosodium saltHMDB
1-Anilinonaphthalene-8-sulfonic acidHMDB
1-Anilino-8-naphthalenesulfonate, magnesium (2:1)HMDB
1,8-ANSHMDB
1-Anilino-8-naphthalenesulfonate, 3H-labeledHMDB
1-Anilino-8-naphthalenesulfonate, ion(1-)HMDB
1-Anilino-8-naphthalenesulfonate, monoammonium saltHMDB
(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 Weight204.36
Monoisotopic Molecular Weight204.1878
IUPAC Name(1S,6S,7S,8S)-1,3-dimethyl-8-(propan-2-yl)tricyclo[4.4.0.0^{2,7}]dec-3-ene
Traditional Name(1S,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 1-naphthalene sulfonates. These are organic aromatic compounds that contain a naphthalene moiety that carries a sulfonic acid group at the 1-position. Naphthalene is a bicyclic compound that is made up of two fused benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthalene sulfonic acids and derivatives
Direct Parent1-naphthalene sulfonates
Alternative Parents
Substituents
  • 1-naphthalene sulfonate
  • 1-naphthalene sulfonic acid or derivatives
  • Arylsulfonic acid or derivatives
  • 1-sulfo,2-unsubstituted aromatic compound
  • Aniline or substituted anilines
  • Monocyclic benzene moiety
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Organosulfonic acid
  • Secondary amine
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
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
Polarizability16.34 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 IDHMDB0061854
DrugBank IDDB04474
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC11326
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link8-Anilinonaphthalene-1-sulfonic_acid
METLIN IDNot Available
PubChem Compound1369
PDB IDNot Available
ChEBI ID39708
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 ]