Showing Compound Card for Valencene (CDB000674)

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Record Information
Version1.0
Created at2020-03-19 00:50:29 UTC
Updated at2020-12-07 19:07:39 UTC
CannabisDB IDCDB000674
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameValencene
DescriptionValencene belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. Sesquiterpenoids 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), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ). 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. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group from the C-10 to the C-5 position. It is an aroma component of citrus fruits and citrus-derived odorants. It is obtained inexpensively from Valencia oranges. Valencene has also been detected as a volatile compound from cannabis samples (PMID: 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1R-(1alpha,7beta,8alpha))-1,2,3,5,6,7,8,8a-Octahydro-1,8a-dimethyl-7-(1-methylvinyl)naphthaleneChEBI
ent-7BetaH-eremophila-10(1),11-dieneChEBI
(1R-(1a,7b,8a))-1,2,3,5,6,7,8,8a-Octahydro-1,8a-dimethyl-7-(1-methylvinyl)naphthaleneGenerator
(1R-(1Α,7β,8α))-1,2,3,5,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylvinyl)naphthaleneGenerator
ValenceneChEBI
4betaH,5alpha-Eremophila-1(10),11-dienePhytoBank
4βH,5α-Eremophila-1(10),11-dienePhytoBank
(1R,7R,8aS)-1,2,3,5,6,7,8,8a-Octahydro-1,8a-dimethyl-7-(1-methylethenyl)naphthalenePhytoBank
(+)-ValencenePhytoBank
ValencenPhytoBank
Chemical FormulaC15H24
Average Molecular Weight204.36
Monoisotopic Molecular Weight204.1878
IUPAC Name(3R,4aS,5R)-4a,5-dimethyl-3-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene
Traditional Namevalencene
CAS Registry Number4630-07-3
SMILES
C[C@@H]1CCC=C2CC[C@H](C[C@@]12C)C(C)=C
InChI Identifier
InChI=1S/C15H24/c1-11(2)13-8-9-14-7-5-6-12(3)15(14,4)10-13/h7,12-13H,1,5-6,8-10H2,2-4H3/t12-,13-,15+/m1/s1
InChI KeyQEBNYNLSCGVZOH-NFAWXSAZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentEremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
Alternative Parents
Substituents
  • Eremophilane 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
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point123 °C at 11 mmHgWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.86ALOGPS
logP4.52ChemAxon
logS-4.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.45 m³·mol⁻¹ChemAxon
Polarizability26.09 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSValencene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-1900000000-246fdfcf18f46ecfc827Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1490000000-64b1f2c7f108e8d251ee2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0cdr-3920000000-6ec0f8bff5e08c3188eb2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-6900000000-de9b8430cbefd1ff8a232017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-dceadc1eb356d16afae62017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-2e9a22282b05ad9143292017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1910000000-25622133ba47e98f5e5d2017-06-28View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014405
KNApSAcK IDC00034741
Chemspider IDNot Available
KEGG Compound IDC17277
BioCyc IDCPD-7989
BiGG IDNot Available
Wikipedia LinkValencene
METLIN IDNot Available
PubChem Compound9855795
PDB IDNot Available
ChEBI ID61700
References
General References
  1. Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. [PubMed:19932496 ]
  2. Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. [PubMed:17710406 ]
  3. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]