(6aS,10aS)-9-(acetyloxymethyl)-1-hydroxy-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-2-carboxylic acid

Details

• Internal ID: f9434786-02fa-4d7f-a83a-b45c1e3b914b
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > 2,2-dimethyl-1-benzopyrans
• IUPAC Name: (6aS,10aS)-9-(acetyloxymethyl)-1-hydroxy-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-2-carboxylic acid
• InChI: InChI=1S/C24H32O6/c1-5-6-7-8-16-12-19-21(22(26)20(16)23(27)28)17-11-15(13-29-14(2)25)9-10-18(17)24(3,4)30-19/h11-12,17-18,26H,5-10,13H2,1-4H3,(H,27,28)/t17-,18-/m0/s1
• InChI Key: VVGKJYWKBQPUEW-ROUUACIJSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₂O₆
• Molecular Weight: 416.50 g/mol
• Exact Mass: 416.21988874 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 6.40
• Atomic LogP (AlogP): 4.98
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9579	95.79%
Caco-2	+	0.5338	53.38%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8339	83.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8084	80.84%
OATP1B3 inhibitior	+	0.8901	89.01%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7794	77.94%
P-glycoprotein inhibitior	+	0.6460	64.60%
P-glycoprotein substrate	-	0.5644	56.44%
CYP3A4 substrate	+	0.6949	69.49%
CYP2C9 substrate	+	0.8004	80.04%
CYP2D6 substrate	-	0.8736	87.36%
CYP3A4 inhibition	-	0.5384	53.84%
CYP2C9 inhibition	+	0.6562	65.62%
CYP2C19 inhibition	+	0.6544	65.44%
CYP2D6 inhibition	-	0.7879	78.79%
CYP1A2 inhibition	+	0.7896	78.96%
CYP2C8 inhibition	+	0.8712	87.12%
CYP inhibitory promiscuity	+	0.7658	76.58%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7081	70.81%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9275	92.75%
Skin irritation	-	0.7084	70.84%
Skin corrosion	-	0.9485	94.85%
Ames mutagenesis	-	0.6991	69.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.5188	51.88%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.7166	71.66%
skin sensitisation	-	0.7930	79.30%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.4811	48.11%
Acute Oral Toxicity (c)	III	0.6796	67.96%
Estrogen receptor binding	+	0.7865	78.65%
Androgen receptor binding	+	0.7518	75.18%
Thyroid receptor binding	-	0.5098	50.98%
Glucocorticoid receptor binding	+	0.8527	85.27%
Aromatase binding	+	0.6708	67.08%
PPAR gamma	+	0.6784	67.84%
Honey bee toxicity	-	0.8807	88.07%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5076	50.76%
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	47 nM	Ki	via Super-PRED
CHEMBL253	P34972	Cannabinoid CB2 receptor	912 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	99.64%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.92%	96.09%
CHEMBL230	P35354	Cyclooxygenase-2	96.81%	89.63%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.27%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.96%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.06%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.94%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.54%	94.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.99%	97.09%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	86.46%	96.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.32%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.24%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.50%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.30%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.97%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.55%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.50%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.69%	93.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.67%	92.50%
CHEMBL340	P08684	Cytochrome P450 3A4	81.50%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.43%	94.33%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	80.80%	95.17%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.73%	94.42%

Plants that contains it

• Cannabis sativa

Cross-Links

• PubChem: 163097650
• LOTUS: LTS0000115
• wikiData: Q103815810