(2R)-2-[(1S)-1-[(1S,3R,7S,8S,9S,10R,13R,14S,17R)-1,7-dihydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-4,5-dimethyl-2,3-dihydropyran-6-one

Details

• Internal ID: 980a94cb-6538-45f0-ad3e-5646dd8f07f3
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives > Withanolide glycosides and derivatives
• IUPAC Name: (2R)-2-[(1S)-1-[(1S,3R,7S,8S,9S,10R,13R,14S,17R)-1,7-dihydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3C(C=C5C4(C(CC(C5)OC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)O)O)O)O)O)O)O)C)O)C)C
• SMILES (Isomeric): CC1=C(C(=O)O[C@H](C1)[C@@H](C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3[C@@H](C=C5[C@@]4([C@H](C[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O)O)O)C)O)C)C
• InChI: InChI=1S/C40H62O15/c1-16-10-25(53-36(50)17(16)2)18(3)21-6-7-22-29-23(8-9-39(21,22)4)40(5)19(12-24(29)42)11-20(13-28(40)43)52-38-35(49)33(47)31(45)27(55-38)15-51-37-34(48)32(46)30(44)26(14-41)54-37/h12,18,20-35,37-38,41-49H,6-11,13-15H2,1-5H3/t18-,20+,21+,22-,23-,24+,25+,26+,27+,28-,29-,30+,31+,32-,33-,34+,35+,37+,38+,39+,40-/m0/s1
• InChI Key: ZYUUDMNYEWKQSN-VSYHLBNMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₆₂O₁₅
• Molecular Weight: 782.90 g/mol
• Exact Mass: 782.40887127 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): -0.20
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7838	78.38%
Caco-2	-	0.8827	88.27%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8076	80.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8255	82.55%
OATP1B3 inhibitior	-	0.2313	23.13%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	+	0.8321	83.21%
P-glycoprotein inhibitior	+	0.7198	71.98%
P-glycoprotein substrate	+	0.5425	54.25%
CYP3A4 substrate	+	0.7485	74.85%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.8853	88.53%
CYP3A4 inhibition	-	0.9495	94.95%
CYP2C9 inhibition	-	0.9335	93.35%
CYP2C19 inhibition	-	0.9392	93.92%
CYP2D6 inhibition	-	0.9467	94.67%
CYP1A2 inhibition	-	0.9243	92.43%
CYP2C8 inhibition	+	0.6347	63.47%
CYP inhibitory promiscuity	-	0.9590	95.90%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6109	61.09%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9170	91.70%
Skin irritation	+	0.5259	52.59%
Skin corrosion	-	0.9457	94.57%
Ames mutagenesis	-	0.6527	65.27%
Human Ether-a-go-go-Related Gene inhibition	+	0.8505	85.05%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7324	73.24%
skin sensitisation	-	0.9254	92.54%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.5338	53.38%
Acute Oral Toxicity (c)	III	0.4565	45.65%
Estrogen receptor binding	+	0.8412	84.12%
Androgen receptor binding	+	0.7200	72.00%
Thyroid receptor binding	-	0.5842	58.42%
Glucocorticoid receptor binding	+	0.6127	61.27%
Aromatase binding	+	0.6730	67.30%
PPAR gamma	+	0.7404	74.04%
Honey bee toxicity	-	0.6951	69.51%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9296	92.96%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL220	P22303	Acetylcholinesterase	94.53%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.28%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.07%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.87%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.03%	95.93%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.43%	85.14%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	92.20%	93.04%
CHEMBL5103	Q969S8	Histone deacetylase 10	91.96%	90.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.25%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.24%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.04%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.92%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.92%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.19%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.29%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.64%	99.23%
CHEMBL1937	Q92769	Histone deacetylase 2	85.32%	94.75%
CHEMBL5028	O14672	ADAM10	84.81%	97.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.62%	94.00%
CHEMBL2581	P07339	Cathepsin D	84.44%	98.95%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.43%	97.33%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.85%	96.47%
CHEMBL1871	P10275	Androgen Receptor	81.78%	96.43%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.34%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	80.37%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.13%	97.36%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.06%	91.07%

Plants that contains it

• Withania somnifera

Cross-Links

• PubChem: 163077005
• LOTUS: LTS0120681
• wikiData: Q105386441