(2R)-2-[(1S)-1-[(1S,3R,8S,9S,10R,13S,14S,17R)-3-[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-1-hydroxy-10,13-dimethyl-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: 4e8908bb-81cd-4c99-8c84-3bc058642482
• 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,8S,9S,10R,13S,14S,17R)-3-[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-1-hydroxy-10,13-dimethyl-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)COC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)O)O)O)O)O)O)O)O)O)C)C)CO
• 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]3CC=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[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O)O)O)O)C)C)CO
• InChI: InChI=1S/C46H72O20/c1-18-11-27(62-41(59)23(18)14-47)19(2)24-7-8-25-22-6-5-20-12-21(13-31(50)46(20,4)26(22)9-10-45(24,25)3)61-43-37(56)35(54)33(52)30(65-43)17-60-42-39(58)36(55)40(29(16-49)64-42)66-44-38(57)34(53)32(51)28(15-48)63-44/h5,19,21-22,24-40,42-44,47-58H,6-17H2,1-4H3/t19-,21+,22-,24+,25-,26-,27+,28+,29+,30+,31-,32+,33+,34-,35-,36+,37+,38+,39+,40+,42+,43+,44-,45+,46-/m0/s1
• InChI Key: JWDQOQNZKABFDG-KCZQQSFZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₇₂O₂₀
• Molecular Weight: 945.00 g/mol
• Exact Mass: 944.46169468 g/mol
• Topological Polar Surface Area (TPSA): 324.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -2.37
• H-Bond Acceptor: 20
• H-Bond Donor: 12
• Rotatable Bonds: 12

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	-	0.8799	87.99%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8076	80.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8427	84.27%
OATP1B3 inhibitior	-	0.2313	23.13%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	+	0.9385	93.85%
P-glycoprotein inhibitior	+	0.7391	73.91%
P-glycoprotein substrate	+	0.6452	64.52%
CYP3A4 substrate	+	0.7582	75.82%
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	+	0.6997	69.97%
CYP inhibitory promiscuity	-	0.9590	95.90%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6109	61.09%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9089	90.89%
Skin irritation	+	0.5259	52.59%
Skin corrosion	-	0.9457	94.57%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8414	84.14%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7158	71.58%
skin sensitisation	-	0.9254	92.54%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6366	63.66%
Acute Oral Toxicity (c)	III	0.4565	45.65%
Estrogen receptor binding	+	0.8441	84.41%
Androgen receptor binding	+	0.7602	76.02%
Thyroid receptor binding	-	0.5158	51.58%
Glucocorticoid receptor binding	+	0.7258	72.58%
Aromatase binding	+	0.7006	70.06%
PPAR gamma	+	0.7992	79.92%
Honey bee toxicity	-	0.6421	64.21%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.43%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	95.15%	94.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.92%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	94.48%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.86%	97.09%
CHEMBL5103	Q969S8	Histone deacetylase 10	93.24%	90.08%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.42%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.39%	95.56%
CHEMBL1871	P10275	Androgen Receptor	91.95%	96.43%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	91.18%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.82%	89.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	90.63%	93.04%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.48%	100.00%
CHEMBL2581	P07339	Cathepsin D	90.36%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.64%	94.00%
CHEMBL325	Q13547	Histone deacetylase 1	89.23%	95.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.86%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.51%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.30%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	85.36%	94.73%
CHEMBL5028	O14672	ADAM10	85.32%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.85%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	83.08%	92.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.38%	93.56%
CHEMBL3310	Q96DB2	Histone deacetylase 11	82.16%	88.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.14%	96.38%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.13%	97.14%

Plants that contains it

• Withania somnifera

Cross-Links

• PubChem: 163192113
• LOTUS: LTS0013374
• wikiData: Q105136109