Showing Compound Card for alpha-Cubebene (CDB000109)

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Record Information
Version1.0
Created at2020-03-18 23:25:06 UTC
Updated at2020-11-18 16:34:47 UTC
CannabisDB IDCDB000109
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namealpha-Cubebene
DescriptionAlpha-cubebene, also known as cubebene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA; PMID:17467679 ), in the cytoplasm. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the cytosol (PMID: 23746261 ). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements..Alpha-Cubebene is one of the two Cubebene isomers, α- and β-cubebene, both with the molecular formula C15H24, but differ only in the position of a double bond which is endocyclic (part of the five-membered ring) in α-cubebene and exocyclic in β-cubebene. It was first isolated from Piper cubeba berries, known as cubebs, from which the name was derived. The volatile oil distilled from cubebs is a pale green or blue-yellow viscous liquid with a warm woody, slightly camphoraceous odor (consisting of both α- and β-cubebene). In addition to cubeb berries, alpha-cubebene is also found in clove buds, fruit and seeds, cypress, lemon, lime, rosemary and tea tree oils and mandarins and oranges ( Ref:DOI ). Alpha-Cubebene is one of many terpenoids that are found in Cannabis plants (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-alpha-CubebeneChEBI
(1R,5S,6R,7S,10R)-4,10-Dimethyl-7-(propan-2-yl)tricyclo[4.4.0.0(1,5)]dec-3-eneChEBI
(-)-a-CubebeneGenerator
(-)-Α-cubebeneGenerator
a-CubebeneGenerator
Α-cubebeneGenerator
alpha-CubeneneHMDB
Α-cubeneneHMDB
alpha-CubebenePhytoBank
Chemical FormulaC15H24
Average Molecular Weight204.36
Monoisotopic Molecular Weight204.1878
IUPAC Name(1R,5S,6R,7S,10R)-4,10-dimethyl-7-(propan-2-yl)tricyclo[4.4.0.0^{1,5}]dec-3-ene
Traditional Name(1R,5S,6R,7S,10R)-7-isopropyl-4,10-dimethyltricyclo[4.4.0.0^{1,5}]dec-3-ene
CAS Registry Number17699-14-8
SMILES
CC(C)[C@@H]1CC[C@@H](C)[C@@]23CC=C(C)[C@@H]2[C@@H]13
InChI Identifier
InChI=1S/C15H24/c1-9(2)12-6-5-11(4)15-8-7-10(3)13(15)14(12)15/h7,9,11-14H,5-6,8H2,1-4H3/t11-,12+,13-,14-,15+/m1/s1
InChI KeyXUEHVOLRMXNRKQ-KHMAMNHCSA-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
  • Cubebane 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
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.88ALOGPS
logP4.09ChemAxon
logS-5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity65.77 m³·mol⁻¹ChemAxon
Polarizability26.16 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0cdl-6900000000-fc2c2b48c3130ca126082015-03-01View Spectrum
Predicted GC-MSalpha-Cubebene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004v-2900000000-cb9dd96728d976cfde1aSpectrum
Predicted GC-MSalpha-Cubebene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1390000000-5797472d9e7fa529c8bf2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-4930000000-0826dbd6d1b12cad2c7c2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pxr-9500000000-5bf76df99a765e29264d2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-90633cf80137394813422017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-551c8a4137523d4a08912017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fe1-1910000000-fb0a47d8a0a09504ee1b2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0avi-5950000000-2ef16aa9e7547e808fac2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9410000000-bd5a53349560ca7edaac2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9200000000-164aa0685a62957c46792021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0090000000-1bdf848163c08abe4e842021-09-24View Spectrum
NMR
TypeDescriptionView
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0036413
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00003120
Chemspider ID390811
KEGG Compound IDC09647
BioCyc IDCPD-8739
BiGG IDNot Available
Wikipedia LinkCubebene
METLIN IDNot Available
PubChem Compound442359
PDB IDNot Available
ChEBI ID10224
References
General References
  1. 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 ]
  2. Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. [PubMed:17467679 ]
  3. Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. [PubMed:23746261 ]