Cannabidiol

Details

• Internal ID: a86f8b9d-4398-469e-bc5d-d16587933b62
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Aromatic monoterpenoids
• IUPAC Name: 2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol
• InChI: InChI=1S/C21H30O2/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3/h11-13,17-18,22-23H,2,5-10H2,1,3-4H3/t17-,18+/m0/s1
• InChI Key: QHMBSVQNZZTUGM-ZWKOTPCHSA-N
• Popularity: 7,512 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₂
• Molecular Weight: 314.50 g/mol
• Exact Mass: 314.224580195 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 6.50
• Atomic LogP (AlogP): 5.85
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 13956-29-1
• (-)-Cannabidiol
• (-)-trans-Cannabidiol
• Epidiolex
• GWP42003-P
• CARDIOLRX
• delta1(2)-trans-Cannabidiol
• cannabidiolum
• (-)-trans-2-p-Mentha-1,8-dien-3-yl-5-pentylresorcinol
• 19GBJ60SN5
• CHEBI:69478
• DTXSID00871959
• BTX-1204
• BTX-1503
• GWP42003
• GWP-42003-P
• GWP-42003
• (1'R,2'R)-5'-methyl-4-pentyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydrobiphenyl-2,6-diol
• 1,3-Benzenediol, 2-(3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl)-5-pentyl-, (1R-trans)-
• 1,3-BENZENEDIOL, 2-((1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL)-5-PENTYL-
• 2-((1R,6R)-3-METHYL-6-(PROP-1-EN-2-YL)CYCLOHEX-2-EN-1-YL)-5-PENTYLBENZENE-1,3-DIOL
• NanoCDB
• 1,3-benzenediol, 2-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-
• 2-((1R,6R)-3-methyl-6-prop-1-en-2-yl-1-cyclohex-2-enyl)-5-pentylbenzene-1,3-diol
• 2-[(1R,6R)-3-methyl-6-prop-1-en-2-yl-1-cyclohex-2-enyl]-5-pentylbenzene-1,3-diol
• Melody Cloverstrip
• 1,3-Benzenediol, 2-[3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-, (1R-trans)-
• CBD Oil
• Cannabidiol Hemp Oil
• RefChem:6403
• leafPro CBDmed Oil FS QP 3%
• leafPro CBDmed Oil FS QP 5%
• N03AX24
• leafPro CBDmed Oil FS QP 20%
• DTXCID401436151
• leafPro CBDmed Oil T-FS QD 3%
• leafPro CBDmed Oil T-FS QD 5%
• leafPro CBDmed Oil T-FS QD 20%
• leafPro CBDmed Softgels FS QP 20
• leafPro CBDmed Softgels T-FS QD 20
• CBD
• (-)-CBD
• Cannabidiol [USAN]
• 3556-78-3
• 2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol
• CHEMBL190461
• .delta.1(2)-trans-Cannabidiol
• Resorcinol, 2-p-mentha-1,8-dien-3-yl-5-pentyl-, (-)-(E)-
• 2-[1R-3-methyl-6R-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-1,3-benzenediol
• Resorcinol, 2-p-mentha-1,8-dien-3-yl-5-pentyl-, (+-)-
• (+/-)-Cannabidiol
• 1,3-Benzenediol, 2-(4-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl)-5-pentyl-, trans-
• 2-((1R,6R)-6-Isopropenyl-3-methyl-cyclohex-2-enyl)-5-pentyl-benzene-1,3-diol
• 2-(4-Methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol trans-
• (-)-Cannabidiol (CBD)
• UNII-19GBJ60SN5
• Epidiolex (TN)
• P0T
• Cannabidiol (7CI)
• (A+/-)-Cannabidiol
• CANNABIDIOL [MI]
• CANNABIDIOL [INN]
• Cannabidiol, (+/-)-
• D1(2)-trans-Cannabidiol
• AC1LD8G2
• CANNABIDIOL [MART.]
• QJ36T2J3TS
• CANNABIDIOL [USP-RS]
• CANNABIDIOL [WHO-DD]
• (-)-Cannabidiol (Synthetic)
• SCHEMBL119679
• Cannabidiol (JAN/USAN/INN)
• GTPL4150
• orb2299258
• ZYN002
• 2-(6-Isopropenyl-3-methyl-2-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol #
• 2-(6-Isopropenyl-3-methyl-cyclohex-2-enyl)-5-pentyl-benzene-1,3-diol
• Delta(1(2))-trans-cannabidiol
• Cannabidiol, 1mg/ml in Methanol
• 16 - Cannabidiol in supplements
• CANNABIDIOL [ORANGE BOOK]
• DTXSID301038839
• 849 - Cannabidiol (CBD) in food
• BDBM50121429
• BDBM50318484
• HB2785
• AKOS032948358
• DB09061
• FC19666
• NCGC00386518-01
• (-)-Cannabidiol 1.0 mg/ml in Methanol
• AC-34022
• FS-10329
• DB-093531
• Sativex (CBD + THC, fixed-dose oral spray)
• C07578
• D10915
• nabiximols (CBD + THC, fixed-dose oral spray)
• Q422917
• (-)-Cannabidiol (CBD) 100 microg/mL in Methanol
• (-)-Cannabidiol (CBD) 1000 microg/mL in Methanol
• (-)-Cannabidiol (CBD) 250 microg/mL in Acetonitrile
• (3R,4R)-2-p-mentha-1,8-dien-3-yl-5-pentylresorcinol
• Resorcinol, 2-p-mentha-1,8-dien-3-yl-5-pentyl-, (+/-)-
• Resorcinol, 2-p-mentha-1,8-dien-3-yl-5-pentyl-, trans-(-)- (8CI)
• 1,3-Benzenediol, 2-[3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-, trans-
• 2-((1R,6R)-3-METHYL-6-(1-METHYLETHENYL)CYCLOHEX-2-ENYL)-5-PENTYLBENZENE-1,3-DIOL
• 2-(3-methyl-6-prop-1-en-2-yl-1-cyclohex-2-enyl)-5-pentyl-benzene-1,3-diol
• 2-(6-Isopropenyl-3-methyl-cyclohex-2-enyl)-5-pentyl-benzene-1,3-diol (Cannabidiol)
• 2-[(1R,6R)-3-Methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-1,3-benzenediol;CBD
• 2-[(1R,6R)-6-isopropenyl-3-methyl-cyclohex-2-en-1-yl]-5-pentyl-benzene-1,3-diol
• 2-[3-Methyl-6-(methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-1,3-benzenediol
• rel-2-[(1R,6R)-3-Methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-1,3-benzenediol
• (1'R,2'R)-5'-methyl-4-pentyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol
• (1'R,2'R)-5'-methyl-4-pentyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydro[1,1'-biphenyl]-2,6-diol
• 1,3-Benzenediol, 2-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-, rel-
• 1,3-Benzenediol, 2-[3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-, trans-(+/-)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9925	99.25%
Caco-2	+	0.8053	80.53%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6845	68.45%
OATP2B1 inhibitior	-	0.7135	71.35%
OATP1B1 inhibitior	+	0.8882	88.82%
OATP1B3 inhibitior	+	0.9292	92.92%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6021	60.21%
P-glycoprotein inhibitior	+	0.7304	73.04%
P-glycoprotein substrate	-	0.5467	54.67%
CYP3A4 substrate	+	0.6032	60.32%
CYP2C9 substrate	+	0.5892	58.92%
CYP2D6 substrate	+	0.3780	37.80%
CYP3A4 inhibition	+	0.6562	65.62%
CYP2C9 inhibition	+	0.5679	56.79%
CYP2C19 inhibition	+	0.6990	69.90%
CYP2D6 inhibition	-	0.7333	73.33%
CYP1A2 inhibition	+	0.8010	80.10%
CYP2C8 inhibition	+	0.5940	59.40%
CYP inhibitory promiscuity	+	0.9613	96.13%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7411	74.11%
Carcinogenicity (trinary)	Non-required	0.5806	58.06%
Eye corrosion	-	0.9629	96.29%
Eye irritation	-	0.8467	84.67%
Skin irritation	-	0.6798	67.98%
Skin corrosion	-	0.7156	71.56%
Ames mutagenesis	-	0.7591	75.91%
Human Ether-a-go-go-Related Gene inhibition	+	0.7134	71.34%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.7301	73.01%
skin sensitisation	+	0.5383	53.83%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.8000	80.00%
Acute Oral Toxicity (c)	III	0.5953	59.53%
Estrogen receptor binding	+	0.7368	73.68%
Androgen receptor binding	+	0.6853	68.53%
Thyroid receptor binding	+	0.7857	78.57%
Glucocorticoid receptor binding	+	0.6274	62.74%
Aromatase binding	+	0.7494	74.94%
PPAR gamma	+	0.9284	92.84%
Honey bee toxicity	-	0.9385	93.85%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5897	58.97%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL218	P21554	Cannabinoid CB1 receptor	2400 nM; 4350 nM	Ki; Ki	PMID: 20218623; PMID: 23865723
CHEMBL253	P34972	Cannabinoid CB2 receptor	10000 nM; 2860 nM; 372 nM	Ki; Ki; Ki	PMID: 20218623; PMID: 23865723; via Super-PRED
CHEMBL1075322	Q9Y2T6	G-protein coupled receptor 55	445 nM	EC50	PMID: 20218623

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.73%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.34%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.67%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.67%	92.94%
CHEMBL5805	Q9NR97	Toll-like receptor 8	89.39%	96.25%
CHEMBL1951	P21397	Monoamine oxidase A	89.30%	91.49%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.04%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	88.98%	100.00%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	88.95%	92.68%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.25%	96.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.29%	99.17%
CHEMBL5203	P33316	dUTP pyrophosphatase	84.46%	99.18%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.47%	95.89%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	82.82%	92.08%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	82.12%	95.17%
CHEMBL3202	P48147	Prolyl endopeptidase	81.23%	90.65%

Plants that contains it

• Cannabis sativa

Cross-Links

• PubChem: 644019
• NPASS: NPC299568
• ChEMBL: CHEMBL190461
• LOTUS: LTS0229114
• wikiData: Q422917