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alpha-Copaene (FDB001522)

Record Information
Version1.0
Creation date2010-04-08 22:05:00 UTC
Update date2020-09-17 15:30:07 UTC
Primary IDFDB001522
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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). 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).
CAS Number3856-25-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not 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
Polarizability16.34 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H24
IUPAC name(1S,6S,7S,8S)-1,3-dimethyl-8-(propan-2-yl)tricyclo[4.4.0.0^{2,7}]dec-3-ene
InChI IdentifierInChI=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
Isomeric SMILES[H][C@@]12C3C(C)=CC[C@]1([H])[C@]3(C)CC[C@H]2C(C)C
Average Molecular Weight204.357
Monoisotopic Molecular Weight204.187800773
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointBoiling Pt : 248.5 oC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSalpha-Copaene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dl-6910000000-819571f4000f4ce2f677Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0190000000-a9c75307ad9fa7e5726b2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0390000000-12dc458834cb96e2536d2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059i-0920000000-4d0945c6547417b0848d2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-5fefaad65bd188e67a4e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-2342a92a86b61876ef462016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-0950000000-518835a78468ff13b3a12016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09639
Pubchem Compound ID442355
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJVC18-E:KGX47-X
EAFUS IDNot Available
Dr. Duke IDCOPAENE|ALPHA-COPAENE|ALPHA-COPACENE
BIGG IDNot Available
KNApSAcK IDC00003118
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID3856-25-5
GoodScent IDrw1053841
SuperScent IDNot Available
Wikipedia IDCopaene
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
carminativeDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
wood
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
spice
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.