(6aS,8R,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-1,8-diol

Details

• Internal ID: 542ebcd7-b347-4fca-b8ce-89a4bfb725f5
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > 2,2-dimethyl-1-benzopyrans
• IUPAC Name: (6aS,8R,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-1,8-diol
• SMILES (Canonical): CCCCCC1=CC(=C2C3C=C(C(CC3C(OC2=C1)(C)C)O)C)O
• SMILES (Isomeric): CCCCCC1=CC(=C2[C@@H]3C=C([C@@H](C[C@@H]3C(OC2=C1)(C)C)O)C)O
• InChI: InChI=1S/C21H30O3/c1-5-6-7-8-14-10-18(23)20-15-9-13(2)17(22)12-16(15)21(3,4)24-19(20)11-14/h9-11,15-17,22-23H,5-8,12H2,1-4H3/t15-,16+,17-/m1/s1
• InChI Key: INKUWBOHCFHXTJ-IXDOHACOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₃
• Molecular Weight: 330.50 g/mol
• Exact Mass: 330.21949481 g/mol
• Topological Polar Surface Area (TPSA): 49.70 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 4.71
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9945	99.45%
Caco-2	+	0.7137	71.37%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5974	59.74%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.8372	83.72%
OATP1B3 inhibitior	+	0.9795	97.95%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.4727	47.27%
P-glycoprotein inhibitior	-	0.6200	62.00%
P-glycoprotein substrate	+	0.5160	51.60%
CYP3A4 substrate	+	0.6995	69.95%
CYP2C9 substrate	-	0.7786	77.86%
CYP2D6 substrate	+	0.5000	50.00%
CYP3A4 inhibition	+	0.5077	50.77%
CYP2C9 inhibition	-	0.6747	67.47%
CYP2C19 inhibition	+	0.5102	51.02%
CYP2D6 inhibition	-	0.8054	80.54%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	+	0.7100	71.00%
CYP inhibitory promiscuity	+	0.7345	73.45%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6520	65.20%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.9390	93.90%
Skin irritation	-	0.6679	66.79%
Skin corrosion	-	0.9315	93.15%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4061	40.61%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.6545	65.45%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.7703	77.03%
Acute Oral Toxicity (c)	III	0.6284	62.84%
Estrogen receptor binding	+	0.7161	71.61%
Androgen receptor binding	+	0.6904	69.04%
Thyroid receptor binding	+	0.6226	62.26%
Glucocorticoid receptor binding	+	0.7667	76.67%
Aromatase binding	+	0.7339	73.39%
PPAR gamma	+	0.7777	77.77%
Honey bee toxicity	-	0.8890	88.90%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.7047	70.47%
Fish aquatic toxicity	+	0.9861	98.61%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL218	P21554	Cannabinoid CB1 receptor	65 nM	Ki	via Super-PRED
CHEMBL253	P34972	Cannabinoid CB2 receptor	88 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL230	P35354	Cyclooxygenase-2	98.66%	89.63%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.89%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	94.68%	97.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.60%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	93.25%	96.95%
CHEMBL2581	P07339	Cathepsin D	92.20%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.66%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.79%	86.33%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	89.32%	92.68%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	87.67%	92.08%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.32%	92.94%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	86.95%	92.86%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.38%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.18%	99.17%
CHEMBL5805	Q9NR97	Toll-like receptor 8	84.92%	96.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.89%	89.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	84.74%	82.38%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.64%	90.71%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.18%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	83.74%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.05%	95.89%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	82.45%	95.58%
CHEMBL240	Q12809	HERG	82.02%	89.76%
CHEMBL233	P35372	Mu opioid receptor	81.82%	97.93%

Plants that contains it

• Cannabis sativa

Cross-Links

• PubChem: 131707153
• LOTUS: LTS0061560
• wikiData: Q103813397