Cannabis Compound Database: Showing Compound Card for Cannabidiolic acid (CDB000010)

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Created at

2020-03-19 00:35:12 UTC

Updated at

2020-11-18 16:35:09 UTC

CannabisDB ID

CDB000010

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Cannabidiolic acid

Description

Cannabidiolic 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
3-p-Mentha-1,8-dien-3-yl-6-pentyl-beta-resorcylic acid	ChEBI
CBDA	ChEBI
Cannabidiolate	Kegg
3-p-Mentha-1,8-dien-3-yl-6-pentyl-b-resorcylate	Generator
3-p-Mentha-1,8-dien-3-yl-6-pentyl-b-resorcylic acid	Generator
3-p-Mentha-1,8-dien-3-yl-6-pentyl-beta-resorcylate	Generator
3-p-Mentha-1,8-dien-3-yl-6-pentyl-β-resorcylate	Generator
3-p-Mentha-1,8-dien-3-yl-6-pentyl-β-resorcylic acid	Generator
Cannabidiol acid	PhytoBank
Cannabidiolcarboxylic acid	PhytoBank

Chemical Formula

C₂₂H₃₀O₄

Average Molecular Weight

358.48

Monoisotopic Molecular Weight

358.2144

IUPAC Name

2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-6-pentylbenzoic acid

Traditional Name

cannabidiolic acid

CAS Registry Number

1244-58-2

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 Key

WVOLTBSCXRRQFR-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hydroxybenzoic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

resorcinols (CHEBI:3359 )
polyketide (CHEBI:3359 )
dihydroxybenzoic acid (CHEBI:3359 )
phytocannabinoid (CHEBI:3359 )
Other aromatic polyketides (C10784 )
Other aromatic polyketides (LMPK13120003 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.55	ALOGPS
logP	6.63	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	2.91	ChemAxon
pKa (Strongest Basic)	-5.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	105.79 m³·mol⁻¹	ChemAxon
Polarizability	41.05 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Cannabidiolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cannabidiolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cannabidiolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cannabidiolic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cannabidiolic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cannabidiolic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cannabidiolic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Orbitrap 12V, negative	splash10-0a4i-0009000000-85bc59490a6724ad6b5b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 15V, negative	splash10-0a4i-0009000000-3f08ee6746c6933c362c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 17V, negative	splash10-0bti-0019000000-5d252d757f08c36645da	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 22V, negative	splash10-01rb-0397000000-08a98630744837dd563d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 27V, negative	splash10-0002-0491000000-b0c84ead0d9ea8cde70d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 32V, negative	splash10-05bb-0980000000-e377126d1ba8670954b6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 37V, negative	splash10-0adi-1930000000-7cb6f6d0bf7a04c631f5	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 42V, negative	splash10-0a6r-2920000000-a24d607a773a9d56202c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 48V, negative	splash10-056r-4910000000-335a34b8820de0c788ac	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 55V, negative	splash10-004i-6900000000-f3ddeca1410b8aa95721	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 63V, negative	splash10-004i-7900000000-bc5a32bbce246697232c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 71V, negative	splash10-056r-8900000000-a2203d0c0829995493e9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 25V, negative	splash10-000i-0009000000-7e6c3e82e722c9c1eee3	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 25V, negative	splash10-00di-0911000000-587f1106864f63e619e0	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 25V, negative	splash10-0a4i-0900000000-916d6c97a14f3d3f65e4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 25V, negative	splash10-03xr-0090000000-852772798aa442e49b04	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 25V, negative	splash10-00fr-0930000000-b92ffa51c5d1acf8e9a9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 25V, negative	splash10-00dj-0092000000-81253f7d3a539b78d271	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 25V, negative	splash10-004i-0090000000-bb0f4f587a0f85d94994	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-0a4i-0009000000-0a16e264b3d907315ed9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-052f-0009000000-b0c16f95db60a3f04108	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, positive	splash10-0006-0009000000-2d0a62a2029919226f84	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 12V, positive	splash10-0006-0009000000-6ef122f741afb0d57992	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 15V, positive	splash10-0006-0019000000-4510020e2286bf9de8dc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 17V, positive	splash10-0006-0039000000-84a21832b7c257b9827e	2020-07-22	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
cAMP-dependent protein kinase catalytic subunit alpha	PRKACA	19p13.1	P17612	details
cAMP-dependent protein kinase catalytic subunit beta	PRKACB	1p36.1	P22694	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.0728 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.0733 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.0688 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.071 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.0778 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.0643 mg/g dry wt	David S. Wishart,...	details

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002642

Chemspider ID

Not Available

KEGG Compound ID

C10784

BioCyc ID

CPD-7170

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

160570

PDB ID

Not Available

ChEBI ID

3359

References

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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

Showing Compound Card for Cannabidiolic acid (CDB000010)

Structure for CDB000010 (Cannabidiolic acid)

Enzymes