Showing Compound Card for Cannabigerolic acid monomethylether (CDB000011)

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Record Information
Version1.0
Created at2020-03-19 00:34:41 UTC
Updated at2020-11-18 16:35:09 UTC
CannabisDB IDCDB000011
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabigerolic acid monomethylether
DescriptionCannabigerolic acid monomethyl ether or CBGAM is the methylated derivative of cannabigerolic acid in position four of the aromatic ring. As such, it is a phytocannabinoid that belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. As a derivative of cannabigerolic acid, it is derived from olivetolic acid on which the hydrogen at position 3 is substituted by a geranyl group. CBGAM 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). As such, cannabigerolic acid monomethylether can be considered a polyketide and a monoterpenoid. In a study of the biosynthetic pathway of cannabinoid acids using four strains of Cannibus sativa L. (Mexican, Minamioshihara-1 and Domestic-l and 2; D-l and D2), 3 of the 4 strains produced THC as the major constituent but not the Domestic 2 strain, which only produced cannabigerolic acid. The Mexican strain also produced CBGAM as second major constituent ( Ref:DOI ). This suggested that all cannabis plants do not produce THC and some may accumulate other intermediates in the pathway to THC such as CBGAM.  
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC23H34O4
Average Molecular Weight374.52
Monoisotopic Molecular Weight374.2457
IUPAC Name3-(3,7-dimethylocta-2,6-dien-1-yl)-2-hydroxy-4-methoxy-6-pentylbenzoic acid
Traditional Name3-(3,7-dimethylocta-2,6-dien-1-yl)-2-hydroxy-4-methoxy-6-pentylbenzoic acid
CAS Registry Number29624-08-6
SMILES
CCCCCC1=CC(OC)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1C(O)=O
InChI Identifier
InChI=1S/C23H34O4/c1-6-7-8-12-18-15-20(27-5)19(22(24)21(18)23(25)26)14-13-17(4)11-9-10-16(2)3/h10,13,15,24H,6-9,11-12,14H2,1-5H3,(H,25,26)/b17-13+
InChI KeyVAFRUJRAAHLCFZ-GHRIWEEISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentP-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • P-methoxybenzoic acid or derivatives
  • Hydroxybenzoic acid
  • Methoxyphenol
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Salicylic acid or derivatives
  • Salicylic acid
  • Aromatic monoterpenoid
  • Benzoic acid
  • Benzoyl
  • Phenol ether
  • Methoxybenzene
  • Phenoxy compound
  • Anisole
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Vinylogous acid
  • Ether
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • 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
logP5.56ALOGPS
logP7.5ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)2.9ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity113.25 m³·mol⁻¹ChemAxon
Polarizability44.44 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCannabigerolic acid monomethylether, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabigerolic acid monomethylether, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabigerolic acid monomethylether, 2 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 Compound24739091
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Thakker C, Martinez I, San KY, Bennett GN: Succinate production in Escherichia coli. Biotechnol J. 2012 Feb;7(2):213-24. doi: 10.1002/biot.201100061. Epub 2011 Sep 20. [PubMed:21932253 ]
  3. Briere JJ, Favier J, El Ghouzzi V, Djouadi F, Benit P, Gimenez AP, Rustin P: Succinate dehydrogenase deficiency in human. Cell Mol Life Sci. 2005 Oct;62(19-20):2317-24. doi: 10.1007/s00018-005-5237-6. [PubMed:16143825 ]
  4. Rustin P, Rotig A: Inborn errors of complex II--unusual human mitochondrial diseases. Biochim Biophys Acta. 2002 Jan 17;1553(1-2):117-22. doi: 10.1016/s0005-2728(01)00228-6. [PubMed:11803021 ]
  5. Yang M, Soga T, Pollard PJ: Oncometabolites: linking altered metabolism with cancer. J Clin Invest. 2013 Sep;123(9):3652-8. doi: 10.1172/JCI67228. Epub 2013 Sep 3. [PubMed:23999438 ]
  6. Sciacovelli M, Frezza C: Oncometabolites: Unconventional triggers of oncogenic signalling cascades. Free Radic Biol Med. 2016 Nov;100:175-181. doi: 10.1016/j.freeradbiomed.2016.04.025. Epub 2016 Apr 23. [PubMed:27117029 ]
  7. Gupta A, Dwivedi M, Mahdi AA, Khetrapal CL, Bhandari M: Broad identification of bacterial type in urinary tract infection using (1)h NMR spectroscopy. J Proteome Res. 2012 Mar 2;11(3):1844-54. doi: 10.1021/pr2010692. Epub 2012 Jan 31. [PubMed:22292465 ]
  8. Sauer M, Porro D, Mattanovich D, Branduardi P: Microbial production of organic acids: expanding the markets. Trends Biotechnol. 2008 Feb;26(2):100-8. doi: 10.1016/j.tibtech.2007.11.006. Epub 2008 Jan 11. [PubMed:18191255 ]
  9. Becker J, Lange A, Fabarius J, Wittmann C: Top value platform chemicals: bio-based production of organic acids. Curr Opin Biotechnol. 2015 Dec;36:168-75. doi: 10.1016/j.copbio.2015.08.022. Epub 2015 Sep 8. [PubMed:26360870 ]
  10. Gunnarsson IB, Kuglarz M, Karakashev D, Angelidaki I: Thermochemical pretreatments for enhancing succinic acid production from industrial hemp (Cannabis sativa L.). Bioresour Technol. 2015 Apr;182:58-66. doi: 10.1016/j.biortech.2015.01.126. Epub 2015 Feb 4. [PubMed:25682224 ]