[(1S,3R,4S,5S,5aS,9aS)-4-hydroxy-1,3-dimethoxy-6,6,9a-trimethyl-1,3,4,5,5a,7,8,9-octahydrobenzo[e][2]benzofuran-5-yl] acetate

Details

• Internal ID: 39eb4169-ec4f-402e-925c-f8f10e9538f9
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: [(1S,3R,4S,5S,5aS,9aS)-4-hydroxy-1,3-dimethoxy-6,6,9a-trimethyl-1,3,4,5,5a,7,8,9-octahydrobenzo[e][2]benzofuran-5-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(C2=C(C(OC2OC)OC)C3(C1C(CCC3)(C)C)C)O
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@H](C2=C([C@H](O[C@H]2OC)OC)[C@@]3([C@@H]1C(CCC3)(C)C)C)O
• InChI: InChI=1S/C19H30O6/c1-10(20)24-14-13(21)11-12(17(23-6)25-16(11)22-5)19(4)9-7-8-18(2,3)15(14)19/h13-17,21H,7-9H2,1-6H3/t13-,14+,15-,16+,17-,19+/m0/s1
• InChI Key: ZEDMMLGFFDFHCX-OUWVOHMFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₃₀O₆
• Molecular Weight: 354.40 g/mol
• Exact Mass: 354.20423867 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.40
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9921	99.21%
Caco-2	+	0.6939	69.39%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6473	64.73%
OATP2B1 inhibitior	-	0.8577	85.77%
OATP1B1 inhibitior	+	0.8676	86.76%
OATP1B3 inhibitior	+	0.8988	89.88%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.7351	73.51%
P-glycoprotein inhibitior	-	0.5682	56.82%
P-glycoprotein substrate	-	0.8779	87.79%
CYP3A4 substrate	+	0.6371	63.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8713	87.13%
CYP3A4 inhibition	-	0.7091	70.91%
CYP2C9 inhibition	-	0.7365	73.65%
CYP2C19 inhibition	-	0.7796	77.96%
CYP2D6 inhibition	-	0.9039	90.39%
CYP1A2 inhibition	+	0.5269	52.69%
CYP2C8 inhibition	-	0.7245	72.45%
CYP inhibitory promiscuity	-	0.8001	80.01%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4560	45.60%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.8857	88.57%
Skin irritation	-	0.5618	56.18%
Skin corrosion	-	0.9305	93.05%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5999	59.99%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.5841	58.41%
skin sensitisation	-	0.7405	74.05%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.6079	60.79%
Acute Oral Toxicity (c)	III	0.4634	46.34%
Estrogen receptor binding	+	0.7776	77.76%
Androgen receptor binding	+	0.6545	65.45%
Thyroid receptor binding	+	0.6615	66.15%
Glucocorticoid receptor binding	+	0.6481	64.81%
Aromatase binding	-	0.5619	56.19%
PPAR gamma	+	0.5397	53.97%
Honey bee toxicity	-	0.7182	71.82%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6055	60.55%
Fish aquatic toxicity	+	0.9847	98.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.29%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.36%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.03%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.62%	97.25%
CHEMBL2581	P07339	Cathepsin D	84.01%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	83.40%	91.19%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.39%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.10%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.53%	86.33%
CHEMBL5028	O14672	ADAM10	80.04%	97.50%

Plants that contains it

• Cinnamosma madagascariensis

Cross-Links

• PubChem: 163106843
• LOTUS: LTS0113767
• wikiData: Q105373111