(3S,4R,5S)-5-[(1R,2R)-1,2-dihydroxy-2-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]-4-ethyl-4-hydroxy-3-methyloxolan-2-one

Details

• Internal ID: a91e2bed-44d7-4196-ab35-e950727cab24
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: (3S,4R,5S)-5-[(1R,2R)-1,2-dihydroxy-2-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]-4-ethyl-4-hydroxy-3-methyloxolan-2-one
• SMILES (Canonical): CCC1(C(C(=O)OC1C(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)O)C)O
• SMILES (Isomeric): CC[C@]1([C@@H](C(=O)O[C@H]1[C@H]([C@@](C)([C@H]2CC[C@@]3([C@@]2(CC[C@H]4C3=CC(=O)[C@H]5[C@@]4(C[C@@H]([C@@H](C5)O)O)C)C)O)O)O)C)O
• InChI: InChI=1S/C29H44O9/c1-6-28(36)14(2)24(34)38-23(28)22(33)27(5,35)21-8-10-29(37)16-11-18(30)17-12-19(31)20(32)13-25(17,3)15(16)7-9-26(21,29)4/h11,14-15,17,19-23,31-33,35-37H,6-10,12-13H2,1-5H3/t14-,15+,17+,19-,20+,21+,22-,23+,25-,26-,27-,28-,29-/m1/s1
• InChI Key: JWAUYPGAZQEFKS-WTRNDCEGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₄O₉
• Molecular Weight: 536.70 g/mol
• Exact Mass: 536.29853298 g/mol
• Topological Polar Surface Area (TPSA): 165.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.01
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9736	97.36%
Caco-2	-	0.7256	72.56%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7321	73.21%
OATP2B1 inhibitior	-	0.5774	57.74%
OATP1B1 inhibitior	+	0.8791	87.91%
OATP1B3 inhibitior	+	0.9174	91.74%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.5935	59.35%
P-glycoprotein inhibitior	-	0.4684	46.84%
P-glycoprotein substrate	+	0.5925	59.25%
CYP3A4 substrate	+	0.7032	70.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9024	90.24%
CYP3A4 inhibition	+	0.7176	71.76%
CYP2C9 inhibition	-	0.7964	79.64%
CYP2C19 inhibition	-	0.7087	70.87%
CYP2D6 inhibition	-	0.9361	93.61%
CYP1A2 inhibition	-	0.8290	82.90%
CYP2C8 inhibition	+	0.4572	45.72%
CYP inhibitory promiscuity	-	0.8942	89.42%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4807	48.07%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9358	93.58%
Skin irritation	+	0.7148	71.48%
Skin corrosion	-	0.9113	91.13%
Ames mutagenesis	-	0.7170	71.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3645	36.45%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.5490	54.90%
skin sensitisation	-	0.8717	87.17%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8849	88.49%
Acute Oral Toxicity (c)	III	0.3272	32.72%
Estrogen receptor binding	+	0.7075	70.75%
Androgen receptor binding	+	0.7506	75.06%
Thyroid receptor binding	+	0.5561	55.61%
Glucocorticoid receptor binding	+	0.7086	70.86%
Aromatase binding	+	0.7031	70.31%
PPAR gamma	+	0.5295	52.95%
Honey bee toxicity	-	0.7838	78.38%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9942	99.42%

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	99.85%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.42%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.61%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.37%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.55%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.34%	82.69%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.07%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.15%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.54%	86.33%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	88.50%	94.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.77%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.44%	97.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.14%	96.77%
CHEMBL2581	P07339	Cathepsin D	87.00%	98.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.49%	91.07%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.98%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.86%	89.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.00%	95.71%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.87%	93.04%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.04%	95.89%
CHEMBL1871	P10275	Androgen Receptor	81.27%	96.43%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	80.12%	96.37%

Plants that contains it

• Ajuga reptans

Cross-Links

• PubChem: 163012584
• LOTUS: LTS0043694
• wikiData: Q105136058