(2S)-2-[(1S)-1-[(1S,3R,6S,7R,8R,11S,12S,14R,15R,16R)-6-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,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]oxyoxan-2-yl]oxy-14-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyl-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]ethyl]-5-methyl-2,5-dihydropyran-6-one

Details

• Internal ID: f49a0202-70d2-422c-b911-742337f4b699
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives > Withanolide glycosides and derivatives
• IUPAC Name: (2S)-2-[(1S)-1-[(1S,3R,6S,7R,8R,11S,12S,14R,15R,16R)-6-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,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]oxyoxan-2-yl]oxy-14-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyl-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]ethyl]-5-methyl-2,5-dihydropyran-6-one
• SMILES (Canonical): CC1C=CC(OC1=O)C(C)C2C(CC3(C2(CCC45C3CCC6C4(C5)CCC(C6(C)CO)OC7C(C(C(CO7)O)O)OC8C(C(C(C(O8)COC9C(C(C(C(O9)CO)O)O)O)O)O)O)C)C)O
• SMILES (Isomeric): CC1C=C[C@H](OC1=O)[C@@H](C)[C@H]2[C@@H](C[C@@]3([C@@]2(CC[C@]45[C@H]3CC[C@@H]6[C@]4(C5)CC[C@@H]([C@@]6(C)CO)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O)O)C)C)O
• InChI: InChI=1S/C47H74O19/c1-20-6-7-24(62-39(20)59)21(2)30-22(50)14-45(5)28-9-8-27-43(3,19-49)29(10-11-46(27)18-47(28,46)13-12-44(30,45)4)65-42-38(31(52)23(51)16-60-42)66-41-37(58)35(56)33(54)26(64-41)17-61-40-36(57)34(55)32(53)25(15-48)63-40/h6-7,20-38,40-42,48-58H,8-19H2,1-5H3/t20?,21-,22-,23+,24+,25-,26-,27+,28+,29+,30+,31+,32-,33-,34+,35+,36-,37-,38-,40-,41+,42+,43+,44-,45+,46-,47+/m1/s1
• InChI Key: YABAGJXBBNJGLI-MWLAUSFBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₄O₁₉
• Molecular Weight: 943.10 g/mol
• Exact Mass: 942.48243013 g/mol
• Topological Polar Surface Area (TPSA): 304.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -1.40
• H-Bond Acceptor: 19
• H-Bond Donor: 11
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6302	63.02%
Caco-2	-	0.8882	88.82%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6778	67.78%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8401	84.01%
OATP1B3 inhibitior	+	0.8971	89.71%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.9000	90.00%
P-glycoprotein inhibitior	+	0.7483	74.83%
P-glycoprotein substrate	+	0.6442	64.42%
CYP3A4 substrate	+	0.7291	72.91%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8786	87.86%
CYP3A4 inhibition	-	0.9359	93.59%
CYP2C9 inhibition	-	0.8681	86.81%
CYP2C19 inhibition	-	0.8739	87.39%
CYP2D6 inhibition	-	0.9532	95.32%
CYP1A2 inhibition	-	0.8976	89.76%
CYP2C8 inhibition	+	0.6479	64.79%
CYP inhibitory promiscuity	-	0.9622	96.22%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6953	69.53%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9070	90.70%
Skin irritation	-	0.6190	61.90%
Skin corrosion	-	0.9454	94.54%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8581	85.81%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.7512	75.12%
skin sensitisation	-	0.9190	91.90%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8126	81.26%
Acute Oral Toxicity (c)	I	0.6705	67.05%
Estrogen receptor binding	+	0.8227	82.27%
Androgen receptor binding	+	0.7444	74.44%
Thyroid receptor binding	-	0.5347	53.47%
Glucocorticoid receptor binding	+	0.7457	74.57%
Aromatase binding	+	0.6368	63.68%
PPAR gamma	+	0.7984	79.84%
Honey bee toxicity	-	0.6383	63.83%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9052	90.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.63%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.29%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	97.43%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.07%	97.09%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	94.75%	83.57%
CHEMBL2581	P07339	Cathepsin D	93.41%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.28%	95.56%
CHEMBL325	Q13547	Histone deacetylase 1	92.17%	95.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.29%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.20%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.17%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.99%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.92%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.68%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.37%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.14%	95.89%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.52%	95.71%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.49%	96.77%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.08%	92.88%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	84.78%	82.38%
CHEMBL226	P30542	Adenosine A1 receptor	84.34%	95.93%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.69%	95.83%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.96%	94.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.89%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	80.26%	92.50%

Plants that contains it

• Aquilegia flabellata

Cross-Links

• PubChem: 100978845
• LOTUS: LTS0234590
• wikiData: Q105345282