Showing Compound Card for Cannabielsoic acid A (CDB000423)

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Record Information
Version1.0
Created at2020-03-19 00:36:14 UTC
Updated at2020-11-18 16:35:10 UTC
CannabisDB IDCDB000423
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabielsoic acid A
DescriptionCannabielsoic acid A, also known as cannabielsoate A or CBEA-C5 A, is a phytocannabinoid that belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Cannabielsoic acid A is a dihydroxybenzoic acid derived from cannabidiolic acid. As such, 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, cannabielsoic acid A can be considered a polyketide, a monoterpenoid and a resorcinol derivative, due to the meta arrangement of its two hydroxil groups on the bencene ring. Cannabielsoic acid A, also belongs to the class of cannabis compounds known as Cannabielsoins. There are two types of cannabielsoic acids, cannabielsoic acid A (CBEA-C5 A) and cannabielsoic acid B (CBEA-C5 B). The inclusion of cannabielsoic acids as Cannabis natural products is somewhat controversial because they have been isolated and identified infrequently and because they can be obtained by the photo-oxidation of CBD (cannabidiol). However, cannabielsoic acids have been repeatedly mentioned in the literature as natural cannabinoids and are considered as a part of the 120 cannabinoid compounds found in cannabis plants (PMID: 6991645 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Cannabielsoate aGenerator
Chemical FormulaC22H30O5
Average Molecular Weight374.48
Monoisotopic Molecular Weight374.2093
IUPAC Name(1R,9S,10S,13R)-3,10-dihydroxy-10-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-2(7),3,5-triene-4-carboxylic acid
Traditional Name(1R,9S,10S,13R)-3,10-dihydroxy-10-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-2(7),3,5-triene-4-carboxylic acid
CAS Registry NumberNot Available
SMILES
CCCCCC1=CC2=C([C@@H]3[C@H](O2)[C@@](C)(O)CC[C@H]3C(C)=C)C(O)=C1C(O)=O
InChI Identifier
InChI=1S/C22H30O5/c1-5-6-7-8-13-11-15-18(19(23)16(13)21(24)25)17-14(12(2)3)9-10-22(4,26)20(17)27-15/h11,14,17,20,23,26H,2,5-10H2,1,3-4H3,(H,24,25)/t14-,17+,20-,22-/m0/s1
InChI KeyOQCOBNKTUMOOHJ-RSGMMRJUSA-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
  • Hydroxybenzoic acid
  • Salicylic acid or derivatives
  • P-menthane monoterpenoid
  • Coumaran
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Cyclic alcohol
  • Vinylogous acid
  • Tertiary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP4.08ALOGPS
logP5.31ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)2.9ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity104.2 m³·mol⁻¹ChemAxon
Polarizability41.96 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCannabielsoic acid A, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabielsoic acid A, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabielsoic acid A, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabielsoic acid A, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabielsoic acid A, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabielsoic acid A, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabielsoic acid A, 3 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 Compound59444405
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 ]