(2S)-2-[(1S)-1-[(4S,5R,6S,8S,9S,10R,13S,14S,17R)-6-[[(4S,5R,6S,8S,9S,10R,13S,14S,17R)-4,5-dihydroxy-17-[(1S)-1-[(2S)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-6-yl]sulfanyl]-4,5-dihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one

Details

• Internal ID: 612123b7-906d-4301-a1b4-200ce9aec2b1
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: (2S)-2-[(1S)-1-[(4S,5R,6S,8S,9S,10R,13S,14S,17R)-6-[[(4S,5R,6S,8S,9S,10R,13S,14S,17R)-4,5-dihydroxy-17-[(1S)-1-[(2S)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-6-yl]sulfanyl]-4,5-dihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-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(C5(C4(C(=O)C=CC5O)C)O)SC6CC7C8CCC(C8(CCC7C9(C6(C(C=CC9=O)O)O)C)C)C(C)C1CC(=C(C(=O)O1)CO)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]3C[C@@H]([C@]5([C@@]4(C(=O)C=C[C@@H]5O)C)O)S[C@H]6C[C@H]7[C@@H]8CC[C@@H]([C@]8(CC[C@@H]7[C@@]9([C@]6([C@H](C=CC9=O)O)O)C)C)[C@H](C)[C@@H]1CC(=C(C(=O)O1)CO)C)C)CO
• InChI: InChI=1S/C56H78O12S/c1-27-21-41(67-49(63)33(27)25-57)29(3)35-9-11-37-31-23-47(55(65)45(61)15-13-43(59)53(55,7)39(31)17-19-51(35,37)5)69-48-24-32-38-12-10-36(30(4)42-22-28(2)34(26-58)50(64)68-42)52(38,6)20-18-40(32)54(8)44(60)14-16-46(62)56(48,54)66/h13-16,29-32,35-42,45-48,57-58,61-62,65-66H,9-12,17-26H2,1-8H3/t29-,30-,31-,32-,35+,36+,37-,38-,39-,40-,41-,42-,45-,46-,47-,48-,51+,52+,53-,54-,55+,56+/m0/s1
• InChI Key: OCURLCGFNKYNMO-GZBQOVFZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₆H₇₈O₁₂S
• Molecular Weight: 975.30 g/mol
• Exact Mass: 974.52139909 g/mol
• Topological Polar Surface Area (TPSA): 233.00 Ų
• XlogP: 7.50
• Atomic LogP (AlogP): 6.38
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7459	74.59%
Caco-2	-	0.8591	85.91%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7754	77.54%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8300	83.00%
OATP1B3 inhibitior	+	0.8959	89.59%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.5452	54.52%
BSEP inhibitior	+	0.9571	95.71%
P-glycoprotein inhibitior	+	0.7518	75.18%
P-glycoprotein substrate	+	0.6696	66.96%
CYP3A4 substrate	+	0.7424	74.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8982	89.82%
CYP3A4 inhibition	-	0.8371	83.71%
CYP2C9 inhibition	-	0.8989	89.89%
CYP2C19 inhibition	-	0.7846	78.46%
CYP2D6 inhibition	-	0.9379	93.79%
CYP1A2 inhibition	-	0.8575	85.75%
CYP2C8 inhibition	+	0.5112	51.12%
CYP inhibitory promiscuity	-	0.9385	93.85%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5544	55.44%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9006	90.06%
Skin irritation	-	0.5623	56.23%
Skin corrosion	-	0.9372	93.72%
Ames mutagenesis	-	0.5392	53.92%
Human Ether-a-go-go-Related Gene inhibition	+	0.7001	70.01%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5095	50.95%
skin sensitisation	-	0.8979	89.79%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.5983	59.83%
Acute Oral Toxicity (c)	III	0.5133	51.33%
Estrogen receptor binding	+	0.7959	79.59%
Androgen receptor binding	+	0.7767	77.67%
Thyroid receptor binding	+	0.6006	60.06%
Glucocorticoid receptor binding	+	0.7647	76.47%
Aromatase binding	+	0.6334	63.34%
PPAR gamma	+	0.8122	81.22%
Honey bee toxicity	-	0.7259	72.59%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9852	98.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.70%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.73%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.74%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	92.33%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.82%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.19%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.27%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.27%	97.14%
CHEMBL5103	Q969S8	Histone deacetylase 10	87.17%	90.08%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.15%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.94%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	84.27%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.21%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.50%	99.23%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.43%	93.99%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	82.86%	96.37%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.03%	93.04%
CHEMBL226	P30542	Adenosine A1 receptor	81.01%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.87%	86.33%
CHEMBL3310	Q96DB2	Histone deacetylase 11	80.67%	88.56%
CHEMBL5028	O14672	ADAM10	80.41%	97.50%

Plants that contains it

• Withania somnifera

Cross-Links

• PubChem: 102155178
• LOTUS: LTS0102343
• wikiData: Q105189599