Showing Compound Card for Cannabidiolic acid (CDB000010)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Show more...
Record Information
Version1.0
Created at2020-03-19 00:35:12 UTC
Updated at2020-11-18 16:35:09 UTC
CannabisDB IDCDB000010
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabidiolic acid
DescriptionCannabidiolic acid (CBDA) belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and, at least, one hydroxyl group. CBDA also belongs to the class of cannabis compounds known as cannabidiol. The biosynthesis of CBDA occurs through the cyclization of the isoprenoid side chain of cannabigerolic acid (CBGA) to yield a cyclohexene moiety, common to all cannabidiol-type cannabinoids. CBDA is one of the major cannabinoid compounds found in cannabis plants, particularly in the fiber-type varieties. Even though CBDA is a non-psychoactive component of Cannabis sativa, it has been proven to inhibit the migration of the highly invasive human breast cancer cell line MDA-MB-231. The apparent mechanism of action involves the inhibition of cAMP-dependent protein kinase A and the activation of Ras homolog family member A (RhoA; PMID: 22963825 ). Studies on mice have also shown that CBDA has a potential anticonvulsant activity (PMID: 31686510 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3-p-Mentha-1,8-dien-3-yl-6-pentyl-beta-resorcylic acidChEBI
CBDAChEBI
CannabidiolateKegg
3-p-Mentha-1,8-dien-3-yl-6-pentyl-b-resorcylateGenerator
3-p-Mentha-1,8-dien-3-yl-6-pentyl-b-resorcylic acidGenerator
3-p-Mentha-1,8-dien-3-yl-6-pentyl-beta-resorcylateGenerator
3-p-Mentha-1,8-dien-3-yl-6-pentyl-β-resorcylateGenerator
3-p-Mentha-1,8-dien-3-yl-6-pentyl-β-resorcylic acidGenerator
Cannabidiol acidPhytoBank
Cannabidiolcarboxylic acidPhytoBank
Chemical FormulaC22H30O4
Average Molecular Weight358.48
Monoisotopic Molecular Weight358.2144
IUPAC Name2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-6-pentylbenzoic acid
Traditional Namecannabidiolic acid
CAS Registry Number1244-58-2
SMILES
CCCCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(O)=C1C(O)=O
InChI Identifier
InChI=1S/C22H30O4/c1-5-6-7-8-15-12-18(23)20(21(24)19(15)22(25)26)17-11-14(4)9-10-16(17)13(2)3/h11-12,16-17,23-24H,2,5-10H2,1,3-4H3,(H,25,26)/t16-,17+/m0/s1
InChI KeyWVOLTBSCXRRQFR-DLBZAZTESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Dihydroxybenzoic acid
  • Aromatic monoterpenoid
  • P-menthane monoterpenoid
  • Salicylic acid
  • Salicylic acid or derivatives
  • Hydroxybenzoic acid
  • Monoterpenoid
  • Monocyclic monoterpenoid
  • Benzoic acid
  • Benzoyl
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
logP4.55ALOGPS
logP6.63ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)2.91ChemAxon
pKa (Strongest Basic)-5.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity105.79 m³·mol⁻¹ChemAxon
Polarizability41.05 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-MSCannabidiolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabidiolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabidiolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabidiolic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabidiolic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabidiolic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabidiolic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
cAMP-dependent protein kinase catalytic subunit alphaPRKACA19p13.1P17612 details
cAMP-dependent protein kinase catalytic subunit betaPRKACB1p36.1P22694 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.0728 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.0733 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.0688 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.071 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.0778 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.0643 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002642
Chemspider IDNot Available
KEGG Compound IDC10784
BioCyc IDCPD-7170
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound160570
PDB IDNot Available
ChEBI ID3359
References
General References
  1. Takeda S, Okajima S, Miyoshi H, Yoshida K, Okamoto Y, Okada T, Amamoto T, Watanabe K, Omiecinski CJ, Aramaki H: Cannabidiolic acid, a major cannabinoid in fiber-type cannabis, is an inhibitor of MDA-MB-231 breast cancer cell migration. Toxicol Lett. 2012 Nov 15;214(3):314-9. doi: 10.1016/j.toxlet.2012.08.029. Epub 2012 Sep 8. [PubMed:22963825 ]
  2. Anderson LL, Low IK, Banister SD, McGregor IS, Arnold JC: Pharmacokinetics of Phytocannabinoid Acids and Anticonvulsant Effect of Cannabidiolic Acid in a Mouse Model of Dravet Syndrome. J Nat Prod. 2019 Nov 22;82(11):3047-3055. doi: 10.1021/acs.jnatprod.9b00600. Epub 2019 Nov 5. [PubMed:31686510 ]
  3. Xiao S, Yu PH: A fluorometric high-performance liquid chromatography procedure for simultaneous determination of methylamine and aminoacetone in blood and tissues. Anal Biochem. 2009 Jan 1;384(1):20-6. doi: 10.1016/j.ab.2008.09.029. Epub 2008 Sep 25. [PubMed:18845121 ]
  4. Pirisino R, Ghelardini C, De Siena G, Malmberg P, Galeotti N, Cioni L, Banchelli G, Raimondi L: Methylamine: a new endogenous modulator of neuron firing? Med Sci Monit. 2005 Aug;11(8):RA257-61. Epub 2005 Jul 25. [PubMed:16049393 ]
  5. Dunkel P, Gelain A, Barlocco D, Haider N, Gyires K, Sperlagh B, Magyar K, Maccioni E, Fadda A, Matyus P: Semicarbazide-sensitive amine oxidase/vascular adhesion protein 1: recent developments concerning substrates and inhibitors of a promising therapeutic target. Curr Med Chem. 2008;15(18):1827-39. doi: 10.2174/092986708785133022. [PubMed:18691041 ]
  6. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]

Enzymes

Enzyme Details
1. cAMP-dependent protein kinase catalytic subunit alpha
General function:
Involved in protein serine/threonine kinase activity
Specific function:
Phosphorylates a large number of substrates in the cytoplasm and the nucleus
Gene Name:
PRKACA
Uniprot ID:
P17612
Molecular weight:
40589.4
Enzyme Details
2. cAMP-dependent protein kinase catalytic subunit beta
General function:
Involved in protein serine/threonine kinase activity
Specific function:
Mediates cAMP-dependent signaling triggered by receptor binding to GPCRs. PKA activation regulates diverse cellular processes such as cell proliferation, the cell cycle, differentiation and regulation of microtubule dynamics, chromatin condensation and decondensation, nuclear envelope disassembly and reassembly, as well as regulation of intracellular transport mechanisms and ion flux
Gene Name:
PRKACB
Uniprot ID:
P22694
Molecular weight:
40622.4