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

Details

• Internal ID: 81c26e70-8158-4980-b40b-2405f72ea44e
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives > Withanolide glycosides and derivatives
• IUPAC Name: (2R)-2-[(1R)-1-hydroxy-1-[(1S,3R,8S,9S,10R,13S,14S,17S)-1-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)(C2CCC3C2(CCC4C3CC=C5C4(C(CC(C5)OC6C(C(C(C(O6)CO)O)O)O)O)C)C)O)CO
• SMILES (Isomeric): CC1=C(C(=O)O[C@H](C1)[C@@](C)([C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4([C@H](C[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)C)C)O)CO
• InChI: InChI=1S/C34H52O11/c1-16-11-26(45-30(41)20(16)14-35)34(4,42)24-8-7-21-19-6-5-17-12-18(43-31-29(40)28(39)27(38)23(15-36)44-31)13-25(37)33(17,3)22(19)9-10-32(21,24)2/h5,18-19,21-29,31,35-40,42H,6-15H2,1-4H3/t18-,19+,21+,22+,23-,24+,25+,26-,27-,28+,29-,31-,32+,33+,34-/m1/s1
• InChI Key: PPVGSQLWWLPFCH-MESVUKEDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₅₂O₁₁
• Molecular Weight: 636.80 g/mol
• Exact Mass: 636.35096247 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.10
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 6

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	-	0.8736	87.36%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8076	80.76%
OATP2B1 inhibitior	-	0.5804	58.04%
OATP1B1 inhibitior	+	0.8617	86.17%
OATP1B3 inhibitior	-	0.2313	23.13%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	-	0.7018	70.18%
P-glycoprotein inhibitior	+	0.6679	66.79%
P-glycoprotein substrate	+	0.5078	50.78%
CYP3A4 substrate	+	0.7629	76.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8896	88.96%
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	+	0.6526	65.26%
CYP inhibitory promiscuity	-	0.9590	95.90%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6109	61.09%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9326	93.26%
Skin irritation	+	0.5259	52.59%
Skin corrosion	-	0.9457	94.57%
Ames mutagenesis	-	0.7170	71.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7057	70.57%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.6173	61.73%
skin sensitisation	-	0.9254	92.54%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.4753	47.53%
Acute Oral Toxicity (c)	III	0.4565	45.65%
Estrogen receptor binding	+	0.7386	73.86%
Androgen receptor binding	+	0.7627	76.27%
Thyroid receptor binding	-	0.6475	64.75%
Glucocorticoid receptor binding	+	0.6309	63.09%
Aromatase binding	+	0.6679	66.79%
PPAR gamma	+	0.6294	62.94%
Honey bee toxicity	-	0.7249	72.49%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
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
CHEMBL1937	Q92769	Histone deacetylase 2	95.37%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.64%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.16%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.14%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.84%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.02%	96.09%
CHEMBL5103	Q969S8	Histone deacetylase 10	91.94%	90.08%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.08%	100.00%
CHEMBL1871	P10275	Androgen Receptor	90.23%	96.43%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.29%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.22%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.19%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.80%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	88.50%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.27%	95.89%
CHEMBL2581	P07339	Cathepsin D	86.78%	98.95%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	85.62%	97.33%
CHEMBL5028	O14672	ADAM10	84.70%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.53%	99.23%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.36%	97.36%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.71%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.06%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.89%	93.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.57%	93.04%
CHEMBL5255	O00206	Toll-like receptor 4	80.19%	92.50%

Plants that contains it

• Withania somnifera

Cross-Links

• PubChem: 10952344
• LOTUS: LTS0000988
• wikiData: Q105213057