Cannabichromene

Details

• Internal ID: 85c7be5c-326b-4681-85c6-716fb9f4ac16
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans
• IUPAC Name: 2-methyl-2-(4-methylpent-3-enyl)-7-pentylchromen-5-ol
• SMILES (Canonical): CCCCCC1=CC(=C2C=CC(OC2=C1)(C)CCC=C(C)C)O
• SMILES (Isomeric): CCCCCC1=CC(=C2C=CC(OC2=C1)(C)CCC=C(C)C)O
• InChI: InChI=1S/C21H30O2/c1-5-6-7-10-17-14-19(22)18-11-13-21(4,23-20(18)15-17)12-8-9-16(2)3/h9,11,13-15,22H,5-8,10,12H2,1-4H3
• InChI Key: UVOLYTDXHDXWJU-UHFFFAOYSA-N
• Popularity: 76 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): 29.50 Ų
• XlogP: 6.90
• Atomic LogP (AlogP): 6.04
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

• Cannabichrome
• 20675-51-8
• Cannanbichromene
• Pentylcannabichromene
• Cannabinochromene
• (+/-)-Cannabichromene
• 2-methyl-2-(4-methylpent-3-enyl)-7-pentylchromen-5-ol
• Cannabichromene (CBC)
• CHEBI:3357
• CHEMBL422704
• UNII-K4497H250W
• 2-Methyl-2-(4-methyl-3-pentenyl)-7-pentyl-2H-1-benzopyran-5-ol
• 2H-1-Benzopyran-5-ol, 2-methyl-2-(4-methyl-3-pentenyl)-7-pentyl-
• K4497H250W
• NSC-291831
• CBC
• 2-Methyl-2-(4-methylpent-3-en-1-yl)-7-pentyl-2H-chromen-5-ol
• 2H-1-Benzopyran-5-ol, 2-methyl-2-(4-methyl-3-penten-1-yl)-7-pentyl-
• 2-methyl-2-(4-methylpent-3-enyl)-7-pentyl-chromen-5-ol
• Cannabichchromene
• (.+/-.)-Cannabichromene
• SCHEMBL144938
• (+/-)-Cannabichromene (CBC)
• GTPL11093
• DTXSID80942873
• BDBM50318486
• NSC291831
• AKOS032948832
• DB14735
• 2H-1-Benzopyran-5-ol, (.+-.)-
• LS-39404
• C08998
• Cannabichromene (CBC) 100 microg/mL in Methanol
• Q410949
• Cannabichromene (CBC) 1000 microg/mL in Methanol
• Cannabichromene (CBC) 250 microg/mL in Acetonitrile
• 2-Methyl-2-(4-methyl-3-pentenyl)-7-pentyl-2H-chromen-5-ol
• 2-METHYL-2-(4-METHYLPENT-3-ENYL)-7-PENTYL-5-CHROMENOL
• 2-methyl-2-(4-methyl-3-penten-1-yl)-7-pentyl-2H-1-benzopyran-5-ol
• 2-Methyl-2-(4-methyl-pent-3-enyl)-7-pentyl-2H-chromen-5-ol(cannabichromene)
• 2H-1-Benzopyran-5-ol, 2-methyl-2-(4-methyl-3-pentenyl)-7-pentyl-, (.+.)-
• 2H-1-Benzopyran-5-ol, 2-methyl-2-(4-methyl-3-pentenyl)-7-pentyl-, (.+/-.)-
• 18793-28-7

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9949	99.49%
Caco-2	+	0.9426	94.26%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5198	51.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7858	78.58%
OATP1B3 inhibitior	+	0.9665	96.65%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7976	79.76%
P-glycoprotein inhibitior	-	0.5175	51.75%
P-glycoprotein substrate	-	0.6152	61.52%
CYP3A4 substrate	+	0.5913	59.13%
CYP2C9 substrate	+	0.5981	59.81%
CYP2D6 substrate	+	0.4032	40.32%
CYP3A4 inhibition	-	0.6729	67.29%
CYP2C9 inhibition	-	0.6200	62.00%
CYP2C19 inhibition	+	0.6934	69.34%
CYP2D6 inhibition	-	0.7880	78.80%
CYP1A2 inhibition	+	0.5696	56.96%
CYP2C8 inhibition	+	0.5453	54.53%
CYP inhibitory promiscuity	+	0.7435	74.35%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6802	68.02%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.5419	54.19%
Skin irritation	-	0.7095	70.95%
Skin corrosion	-	0.9303	93.03%
Ames mutagenesis	-	0.8254	82.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7250	72.50%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.5699	56.99%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.6394	63.94%
Acute Oral Toxicity (c)	III	0.7899	78.99%
Estrogen receptor binding	+	0.7351	73.51%
Androgen receptor binding	+	0.5341	53.41%
Thyroid receptor binding	+	0.7866	78.66%
Glucocorticoid receptor binding	+	0.6377	63.77%
Aromatase binding	+	0.7396	73.96%
PPAR gamma	+	0.8055	80.55%
Honey bee toxicity	-	0.9209	92.09%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6597	65.97%
Fish aquatic toxicity	+	0.9740	97.40%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL218	P21554	Cannabinoid CB1 receptor	714 nM	Ki	via Super-PRED
CHEMBL253	P34972	Cannabinoid CB2 receptor	257 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.98%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.65%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.46%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	95.53%	94.73%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	95.47%	92.08%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.19%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.25%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	90.20%	91.49%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	89.32%	92.86%
CHEMBL240	Q12809	HERG	89.00%	89.76%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.93%	86.33%
CHEMBL230	P35354	Cyclooxygenase-2	85.34%	89.63%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.17%	96.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.04%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.70%	89.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.58%	100.00%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	81.26%	97.29%

Plants that contains it

• Cannabis sativa
• Tanacetum parthenium

Cross-Links

• PubChem: 30219
• NPASS: NPC218753
• ChEMBL: CHEMBL422704
• LOTUS: LTS0247793
• wikiData: Q410949