(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-(hydroxymethyl)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-2,3-dihydropyran-6-one

Details

• Internal ID: efa79033-befc-4ed7-865b-8bf0494334cf
• 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-(hydroxymethyl)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-2,3-dihydropyran-6-one
• SMILES (Canonical): CC1=CCC(OC1=O)C(C)C2C(CC3(C2(CCC45C3CCC6C4(C5)CCC(C6(C)CO)OC7C(C(C(CO7)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)C)O
• SMILES (Isomeric): CC1=CC[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)O)O)O)C)C)O
• InChI: InChI=1S/C41H64O14/c1-19-6-7-23(52-34(19)50)20(2)28-21(44)14-39(5)26-9-8-25-37(3,18-43)27(10-11-40(25)17-41(26,40)13-12-38(28,39)4)54-36-33(29(46)22(45)16-51-36)55-35-32(49)31(48)30(47)24(15-42)53-35/h6,20-33,35-36,42-49H,7-18H2,1-5H3/t20-,21-,22+,23+,24-,25+,26+,27+,28+,29+,30-,31+,32-,33-,35+,36+,37+,38-,39+,40-,41+/m1/s1
• InChI Key: OKWLDWGMBXBXMR-IZOSBIJVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₄O₁₄
• Molecular Weight: 780.90 g/mol
• Exact Mass: 780.42960671 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 0.92
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7392	73.92%
Caco-2	-	0.8863	88.63%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7140	71.40%
OATP2B1 inhibitior	-	0.8724	87.24%
OATP1B1 inhibitior	+	0.8381	83.81%
OATP1B3 inhibitior	+	0.8905	89.05%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	+	0.8830	88.30%
P-glycoprotein inhibitior	+	0.7629	76.29%
P-glycoprotein substrate	+	0.5509	55.09%
CYP3A4 substrate	+	0.7242	72.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8799	87.99%
CYP3A4 inhibition	-	0.9461	94.61%
CYP2C9 inhibition	-	0.8232	82.32%
CYP2C19 inhibition	-	0.8854	88.54%
CYP2D6 inhibition	-	0.9415	94.15%
CYP1A2 inhibition	-	0.8829	88.29%
CYP2C8 inhibition	+	0.6386	63.86%
CYP inhibitory promiscuity	-	0.9485	94.85%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6790	67.90%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9142	91.42%
Skin irritation	-	0.5548	55.48%
Skin corrosion	-	0.9426	94.26%
Ames mutagenesis	-	0.5870	58.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8352	83.52%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.7209	72.09%
skin sensitisation	-	0.9021	90.21%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.7431	74.31%
Acute Oral Toxicity (c)	I	0.6647	66.47%
Estrogen receptor binding	+	0.7545	75.45%
Androgen receptor binding	+	0.7507	75.07%
Thyroid receptor binding	-	0.6226	62.26%
Glucocorticoid receptor binding	+	0.6736	67.36%
Aromatase binding	+	0.6672	66.72%
PPAR gamma	+	0.7402	74.02%
Honey bee toxicity	-	0.6638	66.38%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9303	93.03%

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	98.90%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.86%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	97.81%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.57%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.28%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.14%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.79%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.10%	89.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	87.75%	83.57%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.90%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.73%	95.89%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.86%	92.88%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.43%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.09%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.34%	94.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.30%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.30%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	82.85%	94.73%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.97%	95.71%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.67%	91.07%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.29%	97.36%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.07%	96.21%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.83%	91.24%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.39%	90.08%

Plants that contains it

• Aquilegia flabellata

Cross-Links

• PubChem: 162925427
• LOTUS: LTS0011841
• wikiData: Q105193805