Cannabidiolic acid

Details

• Internal ID: 742086bf-163e-456c-9299-a25ceadc92f7
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Hydroxybenzoic acid derivatives
• IUPAC Name: 2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-6-pentylbenzoic acid
• 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
• Popularity: 124 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₄
• Molecular Weight: 358.50 g/mol
• Exact Mass: 358.21440943 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 6.60
• Atomic LogP (AlogP): 5.54
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

• 1244-58-2
• CBDA
• FJX8O3OJCD
• CHEBI:3359
• DTXSID80154318
• 3-p-Mentha-1,8-dien-3-yl-6-pentyl-beta-resorcylic acid
• 2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-6-pentylbenzoic acid
• 2,4-dihydroxy-3-((1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl)-6-pentylbenzoic acid
• RefChem:5641
• DTXCID8076809
• 423-050-9
• Cannabidiol Acid
• CHEMBL498672
• Cannabidiolic acid (CBDA)
• Benzoic acid, 2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-6-pentyl-
• UNII-FJX8O3OJCD
• nnabidiolic acid
• BENZOIC ACID, 2,4-DIHYDROXY-3-((1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL)-6-PENTYL-
• 2,4-dihydroxy-3-[(1r,6r)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-6-pentylbenzoic acid
• SCHEMBL141666
• CANNABIDIOLCARBOXYLIC ACID
• SCHEMBL29730444
• GTPL10600
• GLXC-16316
• BDBM50318485
• LMPK13120003
• CANNABIDIOLIC ACID [NFLIS-DRUG]
• FC61419
• FS-10258
• Cannabidiolic acid (CBDA), 1mg/ml in Acetonitrile
• Q27106043
• Cannabidiolic acid (CBDA) 250 microg/mL in Acetonitrile
• Cannabidiolic acid (CBDA) 100 microg/mL in Acetonitrile
• Cannabidiolic acid (CBDA) 1000 microg/mL in Acetonitrile
• 2,4-dihydroxy-3-((1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-enyl)-6-pentylbenzoic acid
• 2,4-dihydroxy-3-[(1R,6R)-6-isopropenyl-3-methyl-cyclohex-2-en-1-yl]-6-pentyl-benzoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9826	98.26%
Caco-2	+	0.6240	62.40%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7875	78.75%
OATP2B1 inhibitior	-	0.5748	57.48%
OATP1B1 inhibitior	+	0.8853	88.53%
OATP1B3 inhibitior	+	0.8989	89.89%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5476	54.76%
P-glycoprotein inhibitior	-	0.5301	53.01%
P-glycoprotein substrate	-	0.5740	57.40%
CYP3A4 substrate	+	0.5927	59.27%
CYP2C9 substrate	-	0.6035	60.35%
CYP2D6 substrate	-	0.8953	89.53%
CYP3A4 inhibition	+	0.5347	53.47%
CYP2C9 inhibition	+	0.5832	58.32%
CYP2C19 inhibition	+	0.6756	67.56%
CYP2D6 inhibition	-	0.7736	77.36%
CYP1A2 inhibition	+	0.6382	63.82%
CYP2C8 inhibition	+	0.6710	67.10%
CYP inhibitory promiscuity	+	0.8579	85.79%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7834	78.34%
Carcinogenicity (trinary)	Non-required	0.6692	66.92%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.7702	77.02%
Skin irritation	-	0.6929	69.29%
Skin corrosion	-	0.9060	90.60%
Ames mutagenesis	-	0.6937	69.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4711	47.11%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5351	53.51%
skin sensitisation	-	0.6000	60.00%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.7631	76.31%
Acute Oral Toxicity (c)	III	0.4465	44.65%
Estrogen receptor binding	+	0.6764	67.64%
Androgen receptor binding	+	0.6616	66.16%
Thyroid receptor binding	+	0.6681	66.81%
Glucocorticoid receptor binding	+	0.7705	77.05%
Aromatase binding	+	0.5416	54.16%
PPAR gamma	+	0.8805	88.05%
Honey bee toxicity	-	0.9515	95.15%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5776	57.76%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.42%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.98%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.61%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.21%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.30%	97.25%
CHEMBL5805	Q9NR97	Toll-like receptor 8	87.20%	96.25%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.98%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.24%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.41%	90.71%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.08%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.43%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.68%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.13%	89.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.34%	94.33%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.20%	95.17%

Plants that contains it

• Cannabis sativa

Cross-Links

• PubChem: 160570
• NPASS: NPC290803
• ChEMBL: CHEMBL498672
• LOTUS: LTS0148227
• wikiData: Q27106043