Showing Compound Card for alpha-Ylangene (CDB000468)

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Record Information
Version1.0
Created at2020-03-19 00:38:33 UTC
Updated at2020-11-18 16:35:11 UTC
CannabisDB IDCDB000468
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namealpha-Ylangene
DescriptionAlpha-Ylangene also known as Ylangene, belongs to the class of organic compounds known as sesquiterpenoids. Sesquiterpenes 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. Alpha-Ylangene is a pale-yellow clear liquid. Alpha-Ylangene is a naturally occurring sesquiterpene found in the leaves of cashew tree (DOI:10.12691/wjac-3-1-2), in grapes (PMID: 17580875 ), and in Cannabis sativa (PMID: 30596146 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC15H24
Average Molecular Weight204.36
Monoisotopic Molecular Weight204.1878
IUPAC Name(1S,2R,6R,7R,8S)-1,3-dimethyl-8-(propan-2-yl)tricyclo[4.4.0.0^{2,7}]dec-3-ene
Traditional Name(1S,2R,6R,7R,8S)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0^{2,7}]dec-3-ene
CAS Registry Number14912-44-8
SMILES
CC(C)[C@@H]1CC[C@@]2(C)[C@@H]3CC=C(C)[C@H]2[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-QRTUWBSPSA-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
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
logP3.75ALOGPS
logP4.09ChemAxon
logS-5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity65.77 m³·mol⁻¹ChemAxon
Polarizability26.11 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View 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 Quantified0.07 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.06 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.06 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.05 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound20055075
PDB IDNot Available
ChEBI IDNot Available
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. Parker M, Pollnitz AP, Cozzolino D, Francis IL, Herderich MJ: Identification and quantification of a marker compound for 'pepper' aroma and flavor in shiraz grape berries by combination of chemometrics and gas chromatography-mass spectrometry. J Agric Food Chem. 2007 Jul 25;55(15):5948-55. doi: 10.1021/jf0705320. Epub 2007 Jun 20. [PubMed:17580875 ]
  4. Gallily R, Yekhtin Z, Hanus LO: The Anti-Inflammatory Properties of Terpenoids from Cannabis. Cannabis Cannabinoid Res. 2018 Dec 26;3(1):282-290. doi: 10.1089/can.2018.0014. eCollection 2018. [PubMed:30596146 ]