Showing Compound Card for Cannabigerol monomethylether (CDB000004)

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Record Information
Version1.0
Created at2020-03-19 00:34:46 UTC
Updated at2020-11-18 16:35:09 UTC
CannabisDB IDCDB000004
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabigerol monomethylether
DescriptionCannabigerol monomethylether is a methoxylated derivative of cannabigerol, which is a phytocannabinoid. Cannabigerol is a resorcinol, due to the meta arrangement of its two hydroxyl groups on the benzene ring. It is biosynthetically derived from olivetolic acid on which the hydrogen at position 3 is substituted by a geranyl group. It is a molecule of mixed biosynthetic origin, in which its aromatic moiety (derived from olivetolic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). Thus, cannabigerol monomethylether can be considered a polyketide, a monoterpenoid and a resorcinol. Cannabigerol is a minor constituent of cannabis (approximately 1 % of dry weight). During growth, most of the cannabigerol present in the plant’s tissues is converted into other cannabinoids, primarily tetrahydrocannabinol (THC) or cannabidiol (CBD) (PMID: 26836472 ). Cannabigerol monomethylether was first reported to be isolated from the japanese “Minamioshihara No.1” domestic variety in 1968 (PMID: 5706840 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC22H34O2
Average Molecular Weight330.51
Monoisotopic Molecular Weight330.2559
IUPAC Name2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-methoxy-5-pentylphenol
Traditional Name2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-methoxy-5-pentylphenol
CAS Registry NumberNot Available
SMILES
CCCCCC1=CC(OC)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1
InChI Identifier
InChI=1S/C22H34O2/c1-6-7-8-12-19-15-21(23)20(22(16-19)24-5)14-13-18(4)11-9-10-17(2)3/h10,13,15-16,23H,6-9,11-12,14H2,1-5H3/b18-13+
InChI KeyKASVLYINZPAMNS-QGOAFFKASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • Aromatic monoterpenoid
  • Methoxyphenol
  • Monocyclic monoterpenoid
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP7.21ALOGPS
logP7.19ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)9.39ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity105.99 m³·mol⁻¹ChemAxon
Polarizability41.56 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCannabigerol monomethylether, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
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
Not Available
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 Compound13864080
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Aizpurua-Olaizola O, Soydaner U, Ozturk E, Schibano D, Simsir Y, Navarro P, Etxebarria N, Usobiaga A: Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes. J Nat Prod. 2016 Feb 26;79(2):324-31. doi: 10.1021/acs.jnatprod.5b00949. Epub 2016 Feb 2. [PubMed:26836472 ]
  2. Yamauchi T, Shoyama Y, Matsuo Y, Nishioka I: Cannabigerol monomethyl ether, a new component of hemp. Chem Pharm Bull (Tokyo). 1968 Jun;16(6):1164-5. doi: 10.1248/cpb.16.1164. [PubMed:5706840 ]