2'''-Episilvestrol

Details

• Internal ID: 91f643ff-243b-4447-9822-7863329ee25c
• Taxonomy: Organoheterocyclic compounds > Benzofurans > Flavaglines
• IUPAC Name: methyl (1R,2R,3S,3aR,8bS)-6-[[(2S,3S,6R)-6-[(1R)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylate
• SMILES (Canonical): COC1C(OC(CO1)C(CO)O)OC2=CC3=C(C(=C2)OC)C4(C(C(C(C4(O3)C5=CC=C(C=C5)OC)C6=CC=CC=C6)C(=O)OC)O)O
• SMILES (Isomeric): CO[C@@H]1[C@@H](O[C@H](CO1)[C@@H](CO)O)OC2=CC3=C(C(=C2)OC)[C@@]4([C@@H]([C@@H]([C@H]([C@@]4(O3)C5=CC=C(C=C5)OC)C6=CC=CC=C6)C(=O)OC)O)O
• InChI: InChI=1S/C34H38O13/c1-40-20-12-10-19(11-13-20)34-27(18-8-6-5-7-9-18)26(30(38)42-3)29(37)33(34,39)28-23(41-2)14-21(15-24(28)47-34)45-32-31(43-4)44-17-25(46-32)22(36)16-35/h5-15,22,25-27,29,31-32,35-37,39H,16-17H2,1-4H3/t22-,25-,26-,27-,29-,31+,32-,33+,34+/m1/s1
• InChI Key: GVKXFVCXBFGBCD-GTDORJALSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₃₈O₁₃
• Molecular Weight: 654.70 g/mol
• Exact Mass: 654.23124126 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.57
• H-Bond Acceptor: 13
• H-Bond Donor: 4
• Rotatable Bonds: 10

Synonyms

• CHEMBL1651030
• CHEBI:70455
• 5'-Episilvestrol
• 5''''''-episilvestrol
• BDBM50335578
• Q27138791
• methyl (1R,2R,3S,3aR,8bS)-6-[[(2S,3S,6R)-6-[(1R)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8140	81.40%
Caco-2	-	0.8298	82.98%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7340	73.40%
OATP2B1 inhibitior	-	0.7162	71.62%
OATP1B1 inhibitior	+	0.8657	86.57%
OATP1B3 inhibitior	+	0.9430	94.30%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9640	96.40%
P-glycoprotein inhibitior	+	0.7504	75.04%
P-glycoprotein substrate	+	0.6740	67.40%
CYP3A4 substrate	+	0.7273	72.73%
CYP2C9 substrate	-	0.6131	61.31%
CYP2D6 substrate	-	0.8245	82.45%
CYP3A4 inhibition	-	0.7214	72.14%
CYP2C9 inhibition	-	0.8594	85.94%
CYP2C19 inhibition	-	0.8178	81.78%
CYP2D6 inhibition	-	0.9424	94.24%
CYP1A2 inhibition	-	0.8361	83.61%
CYP2C8 inhibition	+	0.7451	74.51%
CYP inhibitory promiscuity	-	0.7971	79.71%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5156	51.56%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9160	91.60%
Skin irritation	-	0.8133	81.33%
Skin corrosion	-	0.9525	95.25%
Ames mutagenesis	+	0.5522	55.22%
Human Ether-a-go-go-Related Gene inhibition	+	0.7888	78.88%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.7609	76.09%
skin sensitisation	-	0.8839	88.39%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.6707	67.07%
Acute Oral Toxicity (c)	III	0.4921	49.21%
Estrogen receptor binding	+	0.7613	76.13%
Androgen receptor binding	+	0.7790	77.90%
Thyroid receptor binding	+	0.5797	57.97%
Glucocorticoid receptor binding	+	0.6821	68.21%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6703	67.03%
Honey bee toxicity	-	0.7471	74.71%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8819	88.19%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2052028	P60842	Eukaryotic initiation factor 4A-I	0.8 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.55%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.29%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.86%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.33%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	94.21%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.98%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	93.68%	97.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.04%	92.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.93%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	91.67%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	91.44%	91.07%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.72%	96.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.53%	97.09%
CHEMBL240	Q12809	HERG	90.14%	89.76%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.97%	99.17%
CHEMBL4208	P20618	Proteasome component C5	89.42%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.22%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.67%	96.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.56%	95.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.03%	95.89%
CHEMBL5028	O14672	ADAM10	81.15%	97.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.15%	85.14%

Plants that contains it

• Aglaia foveolata

Cross-Links

• PubChem: 11679084
• NPASS: NPC222665
• ChEMBL: CHEMBL1651030