(1S,4R,6S)-4-[(1S)-1-[(1S,3R,8S,9S,10R,13S,14S,17R)-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]-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-2-one

Details

• Internal ID: 6cf9ca8f-07ff-4837-913a-ef8251001d89
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives > Withanolide glycosides and derivatives
• IUPAC Name: (1S,4R,6S)-4-[(1S)-1-[(1S,3R,8S,9S,10R,13S,14S,17R)-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]-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-2-one
• SMILES (Canonical): CC(C1CCC2C1(CCC3C2CC=C4C3(C(CC(C4)OC5C(C(C(C(O5)CO)O)O)O)O)C)C)C6CC7(C(O7)(C(=O)O6)C)C
• SMILES (Isomeric): C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3([C@H](C[C@@H](C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)C)C)[C@H]6C[C@]7([C@](O7)(C(=O)O6)C)C
• InChI: InChI=1S/C34H52O10/c1-16(23-14-32(3)34(5,44-32)30(40)43-23)20-8-9-21-19-7-6-17-12-18(41-29-28(39)27(38)26(37)24(15-35)42-29)13-25(36)33(17,4)22(19)10-11-31(20,21)2/h6,16,18-29,35-39H,7-15H2,1-5H3/t16-,18+,19-,20+,21-,22-,23+,24+,25-,26+,27-,28+,29+,31+,32-,33-,34+/m0/s1
• InChI Key: OVHWHMIFHTVFRU-CKTIMABZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₅₂O₁₀
• Molecular Weight: 620.80 g/mol
• Exact Mass: 620.35604785 g/mol
• Topological Polar Surface Area (TPSA): 158.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.22
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8542	85.42%
Caco-2	-	0.8672	86.72%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7542	75.42%
OATP2B1 inhibitior	-	0.8612	86.12%
OATP1B1 inhibitior	+	0.8465	84.65%
OATP1B3 inhibitior	+	0.8745	87.45%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	-	0.7122	71.22%
P-glycoprotein inhibitior	+	0.6907	69.07%
P-glycoprotein substrate	+	0.5386	53.86%
CYP3A4 substrate	+	0.7519	75.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8669	86.69%
CYP3A4 inhibition	-	0.9149	91.49%
CYP2C9 inhibition	-	0.7962	79.62%
CYP2C19 inhibition	-	0.8927	89.27%
CYP2D6 inhibition	-	0.9354	93.54%
CYP1A2 inhibition	-	0.8613	86.13%
CYP2C8 inhibition	+	0.6285	62.85%
CYP inhibitory promiscuity	-	0.9419	94.19%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6556	65.56%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9316	93.16%
Skin irritation	+	0.4907	49.07%
Skin corrosion	-	0.9371	93.71%
Ames mutagenesis	-	0.7314	73.14%
Human Ether-a-go-go-Related Gene inhibition	-	0.3981	39.81%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.6283	62.83%
skin sensitisation	-	0.8940	89.40%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.5972	59.72%
Acute Oral Toxicity (c)	I	0.4400	44.00%
Estrogen receptor binding	+	0.6938	69.38%
Androgen receptor binding	+	0.7639	76.39%
Thyroid receptor binding	-	0.6299	62.99%
Glucocorticoid receptor binding	+	0.6321	63.21%
Aromatase binding	+	0.6826	68.26%
PPAR gamma	+	0.5773	57.73%
Honey bee toxicity	-	0.6879	68.79%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9504	95.04%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.86%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.64%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.03%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.92%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	93.47%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	93.16%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.85%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.59%	85.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.38%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.26%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.23%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	88.16%	94.75%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	88.05%	95.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.51%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.27%	95.89%
CHEMBL1871	P10275	Androgen Receptor	85.92%	96.43%
CHEMBL5103	Q969S8	Histone deacetylase 10	84.82%	90.08%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.50%	96.21%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	83.24%	94.23%
CHEMBL2581	P07339	Cathepsin D	82.86%	98.95%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.66%	93.04%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.54%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.60%	99.23%
CHEMBL220	P22303	Acetylcholinesterase	81.40%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.20%	97.14%
CHEMBL5255	O00206	Toll-like receptor 4	81.09%	92.50%

Plants that contains it

• Physalis pubescens

Cross-Links

• PubChem: 162897440
• LOTUS: LTS0027078
• wikiData: Q105200737