LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG SVG

Common Name

Cannabidiolic acid

Systematic Name

Synonyms

LM ID

LMPK13120003

Formula

C₂₂H₃₀O₄

Exact Mass

Calculate m/z

358.214411

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Biological Context

Cannabidiolic acid (CRM) is a certified reference material categorized as a phytocannabinoid.^1,2 Cannabidiolic acid has anxiolytic-like and antinociceptive activities in mice.^2,3 Cannabidiolic acid (CRM) is registered as a Canada Test Kit. This product is intended for research and forensic applications.

This information has been provided by Cayman Chemical

References

1. Vigli, D., Cosentino, L., Pellas, M., et al. Chronic treatment with cannabidiolic scid (CBDA) reduces thermal pain sensitivity in male mice and rescues the hyperalgesia in a mouse model of Rett syndrome. Neuroscience 453, 113-123 (2021).

2. ZagZoog, A., Mohamed, K.A., Kim, H.J.J., et al. In vitro and in vivo pharmacological activity of minor cannabinoids isolated from Cannabis sativa. Sci. Rep. 10(1), 20405 (2020).

3. Taura, F., Morimoto, S., and Shoyama, Y. Purification and characterization of cannabidiolic-acid synthase from Cannabis sativa L.. Biochemical analysis of a novel enzyme that catalyzes the oxidocyclization of cannabigerolic acid to cannabidiolic acid. J. Biol. Chem. 271(29), 17411-17416 (1996).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Cannabis sativa (#3483)

Magnoliopsida (#3398)

Hashish. IV. The isolation and structure of cannabinolic cannabidiolic and cannabigerolic acids.,
Tetrahedron, 1965

Pubmed ID: 5879350

DOI: 10.1016/0040-4020(65)80064-3

String Representations

InChiKey (Click to copy)

WVOLTBSCXRRQFR-DLBZAZTESA-N

InChi (Click to copy)

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

SMILES (Click to copy)

[C@]1([H])([C@H](C(=C)C)CCC(C)=C1)C1C(O)=C(C(O)=O)C(CCCCC)=CC=1O