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

Details

• Internal ID: 43d35c20-064c-4054-a0e7-3d2035d5ff63
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives > Withanolide glycosides and derivatives
• IUPAC Name: [(1S,3R,8S,9S,10R,13S,14S,17S)-17-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-3-[(2R,3R,4R,5R,6R)-3-hydroxy-6-(hydroxymethyl)-4,5-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-2-yl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-1-yl] acetate
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)(C2CCC3C2(CCC4C3CC=C5C4(C(CC(C5)OC6C(C(C(C(O6)CO)OC7C(C(C(C(O7)CO)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)O)OC(=O)C)C)C)O)C
• 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[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)OC(=O)C)C)C)O)C
• InChI: InChI=1S/C48H74O21/c1-19-13-32(67-42(60)20(19)2)48(6,61)30-10-9-25-24-8-7-22-14-23(15-31(62-21(3)52)47(22,5)26(24)11-12-46(25,30)4)63-45-39(59)41(69-44-38(58)36(56)34(54)28(17-50)65-44)40(29(18-51)66-45)68-43-37(57)35(55)33(53)27(16-49)64-43/h7,23-41,43-45,49-51,53-59,61H,8-18H2,1-6H3/t23-,24+,25+,26+,27-,28-,29-,30+,31+,32-,33-,34-,35+,36+,37-,38-,39-,40-,41-,43+,44+,45-,46+,47+,48-/m1/s1
• InChI Key: GMHAMOANCQJEJC-ZOJBMDBOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₄O₂₁
• Molecular Weight: 987.10 g/mol
• Exact Mass: 986.47225936 g/mol
• Topological Polar Surface Area (TPSA): 331.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -1.66
• H-Bond Acceptor: 21
• H-Bond Donor: 11
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7135	71.35%
Caco-2	-	0.8808	88.08%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8629	86.29%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8509	85.09%
OATP1B3 inhibitior	+	0.7884	78.84%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5298	52.98%
BSEP inhibitior	+	0.7285	72.85%
P-glycoprotein inhibitior	+	0.7415	74.15%
P-glycoprotein substrate	+	0.5996	59.96%
CYP3A4 substrate	+	0.7697	76.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9029	90.29%
CYP3A4 inhibition	-	0.9295	92.95%
CYP2C9 inhibition	-	0.9215	92.15%
CYP2C19 inhibition	-	0.9385	93.85%
CYP2D6 inhibition	-	0.9550	95.50%
CYP1A2 inhibition	-	0.8971	89.71%
CYP2C8 inhibition	+	0.7235	72.35%
CYP inhibitory promiscuity	-	0.9438	94.38%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6009	60.09%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9053	90.53%
Skin irritation	+	0.4910	49.10%
Skin corrosion	-	0.9419	94.19%
Ames mutagenesis	-	0.7770	77.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8198	81.98%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.6548	65.48%
skin sensitisation	-	0.9349	93.49%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.4649	46.49%
Acute Oral Toxicity (c)	III	0.5730	57.30%
Estrogen receptor binding	+	0.8459	84.59%
Androgen receptor binding	+	0.7633	76.33%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6992	69.92%
Aromatase binding	+	0.6063	60.63%
PPAR gamma	+	0.7927	79.27%
Honey bee toxicity	-	0.6616	66.16%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9668	96.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.86%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.20%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.48%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.38%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.84%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.99%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	91.66%	94.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.31%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.89%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.86%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.63%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.17%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.27%	93.56%
CHEMBL5103	Q969S8	Histone deacetylase 10	88.08%	90.08%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.29%	97.14%
CHEMBL5255	O00206	Toll-like receptor 4	86.62%	92.50%
CHEMBL3401	O75469	Pregnane X receptor	84.79%	94.73%
CHEMBL5028	O14672	ADAM10	83.92%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.51%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.31%	93.04%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.86%	99.17%
CHEMBL2581	P07339	Cathepsin D	82.75%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.45%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.33%	95.89%

Plants that contains it

• Eriolarynx australis

Cross-Links

• PubChem: 101625610
• LOTUS: LTS0066335
• wikiData: Q105011816