Showing Compound Card for Cannabichromenic acid (CDB000398)

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Record Information
Version1.0
Created at2020-03-19 00:34:58 UTC
Updated at2020-11-18 16:35:09 UTC
CannabisDB IDCDB000398
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabichromenic acid
DescriptionCannabichromenic acid (CBCA) is a biosynthetic derivative of cannabigerolic acid (CBGA). It is a non-psychoactive component of cannabis and is one of the more than 100 cannabinoids found in Cannabis sativa plants. As its precursor, cannabigerolic acid, CBCA is a phytocannabinoid that belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Cannabichromenic acid is characterized by the presence of a chromene moiety in the center of the structure. This chromene arrangement results from the cyclization of the isoprenoid sidechain on to the hydroxyl group in position four of cannabigerolic acid, yielding a pyrane type ring. Cannabichromenic acid 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, cannabichromenic acid can be considered a polyketide, a monoterpenoid and a resorcinol, due to the meta arrangement of its two hydroxyl groups on the benzene ring. CBC is not active at the  cannabinoid-1 (CB1) and cannabinoid-2 (CB2) receptors, but is an agonist of  transient receptor potential ankyrin 1 TRPA1 and less potently, an agonist of  transient receptor potential cation channel, subfamily V, member 3 and 4 (TRPV3;  TRPV4;  PMID 28120231 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5-Hydroxy-2-methyl-2-(4-methylpent-3-enyl)-7-pentylchromene-6-carboxylateGenerator
Chemical FormulaC22H30O4
Average Molecular Weight358.48
Monoisotopic Molecular Weight358.2144
IUPAC Name(2S)-5-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-7-pentyl-2H-chromene-6-carboxylic acid
Traditional Name(2S)-5-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-7-pentylchromene-6-carboxylic acid
CAS Registry Number20408-52-0
SMILES
CCCCCC1=CC2=C(C=C[C@](C)(CCC=C(C)C)O2)C(O)=C1C(O)=O
InChI Identifier
InChI=1S/C22H30O4/c1-5-6-7-10-16-14-18-17(20(23)19(16)21(24)25)11-13-22(4,26-18)12-8-9-15(2)3/h9,11,13-14,23H,5-8,10,12H2,1-4H3,(H,24,25)/t22-/m0/s1
InChI KeyHRHJHXJQMNWQTF-QFIPXVFZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentSalicylic acid and derivatives
Alternative Parents
Substituents
  • Benzopyran
  • Salicylic acid or derivatives
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Vinylogous acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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
logP5.69ALOGPS
logP6.91ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)2.87ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity106.86 m³·mol⁻¹ChemAxon
Polarizability41.69 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCannabichromenic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabichromenic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabichromenic acid, 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 Compound92448135
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turner SE, Williams CM, Iversen L, Whalley BJ: Molecular Pharmacology of Phytocannabinoids. Prog Chem Org Nat Prod. 2017;103:61-101. doi: 10.1007/978-3-319-45541-9_3. [PubMed:28120231 ]