Showing Compound Card for Cannabidiol monomethylether (CDB000012)

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Record Information
Version1.0
Created at2020-03-19 00:35:20 UTC
Updated at2020-11-18 16:35:09 UTC
CannabisDB IDCDB000012
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabidiol monomethylether
DescriptionCannabidiol monomethyl ether (CBDM) is a methoxylated derivative of cannabidiol, which is a phytocannabinoid. Cannabidiol (CBD) is a resorcinol, which has a meta arrangement of its two hydroxyl groups on the benzene ring, one of which is methylated in cannabidiol monomethyl ether. Because of the mixed biosynthetic origins of CBD and CDBM they can also be considered as polyketides and monoterpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). Cannabidiol monomethylether is a neutral compound. In one study using mice, rabbits and rats, cannabidol monomethylether was used as a substrate and caused hypothermia in some rodents (PMID: 1806944 ).  Unlike CBD, research regarding the pharmacological properties of CBDM is scarce.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Cannabidiol monomethyl etherMeSH
Cannabidiol-3-monomethyl ether, trans(+-)-isomerMeSH
Cannabidiol-3-monomethyl etherMeSH
Chemical FormulaC22H32O2
Average Molecular Weight328.5
Monoisotopic Molecular Weight328.2402
IUPAC Name3-methoxy-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-pentylphenol
Traditional Name3-methoxy-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-pentylphenol
CAS Registry Number1972-05-0
SMILES
CCCCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(OC)=C1
InChI Identifier
InChI=1S/C22H32O2/c1-6-7-8-9-17-13-20(23)22(21(14-17)24-5)19-12-16(4)10-11-18(19)15(2)3/h12-14,18-19,23H,2,6-11H2,1,3-5H3/t18-,19+/m0/s1
InChI KeyIPGGELGANIXRSX-RBUKOAKNSA-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
  • P-menthane monoterpenoid
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • 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
logP6.42ALOGPS
logP6.47ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)9.36ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity103.01 m³·mol⁻¹ChemAxon
Polarizability40.3 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCannabidiol 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 Compound164905
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Yamamoto I, Gohda H, Narimatsu S, Watanabe K, Yoshimura H: Cannabielsoin as a new metabolite of cannabidiol in mammals. Pharmacol Biochem Behav. 1991 Nov;40(3):541-6. doi: 10.1016/0091-3057(91)90360-e. [PubMed:1806944 ]