Showing Compound Card for alpha-Guaiene (CDB000453)

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Record Information
Version1.0
Created at2020-03-19 00:37:44 UTC
Updated at2020-12-07 19:07:26 UTC
CannabisDB IDCDB000453
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namealpha-Guaiene
Descriptionalpha-Guaiene (α-guaiene) belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. 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. α-Guaiene is one of three isomers of Guaiene (α-Guaiene, β-Guaiene, and δ-Guaiene). α-Guaiene is the most common member of this group and was first isolated from guaiac wood oil from Bulnesia sarmientoi. It has since been detected in several plant species, including Cannabis sativa (PMID: 31816756 ) The guaienes are used in the fragrance and flavoring industries to impart earthy, spicy aromas and tastes.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
a-GuaieneGenerator
Α-guaieneGenerator
Chemical FormulaC15H24
Average Molecular Weight204.36
Monoisotopic Molecular Weight204.1878
IUPAC Name(1S,4S,7R)-1,4-dimethyl-7-(prop-1-en-2-yl)-1,2,3,4,5,6,7,8-octahydroazulene
Traditional Nameguaiene
CAS Registry Number3691-12-1
SMILES
C[C@H]1CCC2=C1C[C@@H](CC[C@@H]2C)C(C)=C
InChI Identifier
InChI=1S/C15H24/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h11-13H,1,5-9H2,2-4H3/t11-,12-,13+/m0/s1
InChI KeyADIDQIZBYUABQK-RWMBFGLXSA-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
  • 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 PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.8ALOGPS
logP4.46ChemAxon
logS-3.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.26 m³·mol⁻¹ChemAxon
Polarizability26.22 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-MSalpha-Guaiene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ad-3900000000-e706463536eeae389282Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0390000000-ca6fe668203bbe8ab5fd2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-2950000000-1a2ba6895a66bed19ab92017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f9j-5900000000-2f78480fe60f51a83de92017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-85d9f5a453c9140a140c2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-49a48b52de1914c108cf2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2900000000-50b55803c93cfd4d7c3c2017-06-28View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien Dawg (Indica dominant)Detected and Quantified0.17 +/- 0.01 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.18 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.13 mg/g dry wt
    • David S. Wishart,...
 details
Sensi Star (Pure Indica)Detected and Quantified0.16 +/- 0.00 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine Dream (Sativa dominant)Detected and Quantified0.16 +/- 0.00 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00020377
Chemspider IDNot Available
KEGG Compound IDC20161
BioCyc IDCPD-8749
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5317844
PDB IDNot Available
ChEBI ID63443
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. Delgado-Povedano MM, Sanchez-Carnerero Callado C, Priego-Capote F, Ferreiro-Vera C: Untargeted characterization of extracts from Cannabis sativa L. cultivars by gas and liquid chromatography coupled to mass spectrometry in high resolution mode. Talanta. 2020 Feb 1;208:120384. doi: 10.1016/j.talanta.2019.120384. Epub 2019 Sep 25. [PubMed:31816756 ]