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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2D Structure
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Physico-chemical Properties
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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
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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
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-6-pentylbenzoic acid
Synonyms Click here for help
cannabidiol acid [1] | CBDA
Database Links Click here for help
BindingDB Ligand 50318485
ChEMBL Ligand CHEMBL498672
GtoPdb PubChem SID 404859047
PubChem CID 160570
Search Google for chemical match using the InChIKey WVOLTBSCXRRQFR-DLBZAZTESA-N
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UniChem Compound Search for chemical match using the InChIKey WVOLTBSCXRRQFR-DLBZAZTESA-N
UniChem Connectivity Search for chemical match using the InChIKey WVOLTBSCXRRQFR-DLBZAZTESA-N