cannabidiolic acid   Click here for help

GtoPdb Ligand ID: 10600

Synonyms: cannabidiol acid [1] | CBDA
Compound class: Synthetic organic
Comment: Cannabidiolic acid (CBDA) is a phytocannabinoid that is present at a significant concentration in Cannabis sativa [3]. It slowly decarboxylates to cannabidiol within the plant tissue. The decarboxylation process is accelerated by heat. To overcome its inherent instability, the more stable analogue cannabidiolic acid methyl ester (HU-580) was synthesised [4]. In in vivo models CBDA has been shown to produce anti-nausea [2,6-7] and anxiolytic‐like effects [5].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 77.76
Molecular weight 358.21
XLogP 6.85
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCCCCc1cc(O)c(c(c1C(=O)O)O)C1C=C(C)CCC1C(=C)C
Isomeric SMILES CCCCCc1cc(O)c(c(c1C(=O)O)O)[C@@H]1C=C(C)CC[C@H]1C(=C)C
InChI 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Baraldi PG, Preti D, Materazzi S, Geppetti P. (2010)
Transient receptor potential ankyrin 1 (TRPA1) channel as emerging target for novel analgesics and anti-inflammatory agents.
J Med Chem, 53 (14): 5085-107. [PMID:20356305]
2. Bolognini D, Rock EM, Cluny NL, Cascio MG, Limebeer CL, Duncan M, Stott CG, Javid FA, Parker LA, Pertwee RG. (2013)
Cannabidiolic acid prevents vomiting in Suncus murinus and nausea-induced behaviour in rats by enhancing 5-HT1A receptor activation.
Br J Pharmacol, 168 (6): 1456-70. [PMID:23121618]
3. Mechoulam R, Gaoni Y. (1965)
Hashish. IV. The isolation and structure of cannabinolic cannabidiolic and cannabigerolic acids.
Tetrahedron, 21 (5): 1223-9. [PMID:5879350]
4. Pertwee RG, Rock EM, Guenther K, Limebeer CL, Stevenson LA, Haj C, Smoum R, Parker LA, Mechoulam R. (2018)
Cannabidiolic acid methyl ester, a stable synthetic analogue of cannabidiolic acid, can produce 5-HT1A receptor-mediated suppression of nausea and anxiety in rats.
Br J Pharmacol, 175 (1): 100-112. [PMID:29057454]
5. Rock EM, Limebeer CL, Petrie GN, Williams LA, Mechoulam R, Parker LA. (2017)
Effect of prior foot shock stress and Δ9-tetrahydrocannabinol, cannabidiolic acid, and cannabidiol on anxiety-like responding in the light-dark emergence test in rats.
Psychopharmacology (Berl.), 234 (14): 2207-2217. [PMID:28424834]
6. Rock EM, Parker LA. (2013)
Effect of low doses of cannabidiolic acid and ondansetron on LiCl-induced conditioned gaping (a model of nausea-induced behaviour) in rats.
Br J Pharmacol, 169 (3): 685-92. [PMID:23488964]
7. Rock EM, Parker LA. (2015)
Synergy between cannabidiol, cannabidiolic acid, and Δ⁹-tetrahydrocannabinol in the regulation of emesis in the Suncus murinus (house musk shrew).
Behav Neurosci, 129 (3): 368-70. [PMID:26030435]