(2S,3S,5R,9R,10R,13R,14R,17S)-17-[(1R)-1-[(2R)-4-ethyl-5-methyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-2,3,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,9,11,15,16,17-decahydrocyclopenta[a]phenanthrene-6,12-dione

Details

• Internal ID: 599827f7-c203-4017-a84c-8d5c12756747
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: (2S,3S,5R,9R,10R,13R,14R,17S)-17-[(1R)-1-[(2R)-4-ethyl-5-methyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-2,3,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,9,11,15,16,17-decahydrocyclopenta[a]phenanthrene-6,12-dione
• SMILES (Canonical): CCC1=C(C(=O)OC(C1)C(C)(C2CCC3(C2(C(=O)CC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)C
• SMILES (Isomeric): CCC1=C(C(=O)O[C@H](C1)[C@@](C)([C@H]2CC[C@@]3([C@@]2(C(=O)C[C@H]4C3=CC(=O)[C@H]5[C@@]4(C[C@@H]([C@H](C5)O)O)C)C)O)O)C
• InChI: InChI=1S/C29H40O8/c1-6-15-9-24(37-25(34)14(15)2)28(5,35)22-7-8-29(36)17-10-19(30)18-11-20(31)21(32)13-26(18,3)16(17)12-23(33)27(22,29)4/h10,16,18,20-22,24,31-32,35-36H,6-9,11-13H2,1-5H3/t16-,18-,20-,21-,22-,24+,26+,27-,28+,29+/m0/s1
• InChI Key: LLPOMLNTBDOEOC-JDEUSFETSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₀O₈
• Molecular Weight: 516.60 g/mol
• Exact Mass: 516.27231823 g/mol
• Topological Polar Surface Area (TPSA): 141.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 2.16
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9695	96.95%
Caco-2	-	0.6765	67.65%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7475	74.75%
OATP2B1 inhibitior	-	0.7123	71.23%
OATP1B1 inhibitior	+	0.8888	88.88%
OATP1B3 inhibitior	+	0.9016	90.16%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.7491	74.91%
P-glycoprotein inhibitior	-	0.4426	44.26%
P-glycoprotein substrate	+	0.6341	63.41%
CYP3A4 substrate	+	0.7102	71.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9048	90.48%
CYP3A4 inhibition	+	0.5843	58.43%
CYP2C9 inhibition	-	0.8902	89.02%
CYP2C19 inhibition	-	0.8012	80.12%
CYP2D6 inhibition	-	0.9470	94.70%
CYP1A2 inhibition	-	0.8632	86.32%
CYP2C8 inhibition	+	0.4782	47.82%
CYP inhibitory promiscuity	-	0.9521	95.21%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5918	59.18%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.9282	92.82%
Skin irritation	+	0.7318	73.18%
Skin corrosion	-	0.9172	91.72%
Ames mutagenesis	-	0.6454	64.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4848	48.48%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.5771	57.71%
skin sensitisation	-	0.8683	86.83%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7449	74.49%
Acute Oral Toxicity (c)	I	0.3106	31.06%
Estrogen receptor binding	+	0.7778	77.78%
Androgen receptor binding	+	0.7508	75.08%
Thyroid receptor binding	+	0.5290	52.90%
Glucocorticoid receptor binding	+	0.7610	76.10%
Aromatase binding	+	0.7066	70.66%
PPAR gamma	+	0.5871	58.71%
Honey bee toxicity	-	0.8270	82.70%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9899	98.99%

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	99.24%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.36%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.87%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.54%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.14%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.76%	82.69%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.31%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.84%	96.09%
CHEMBL230	P35354	Cyclooxygenase-2	89.88%	89.63%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.91%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.08%	99.23%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.73%	96.61%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.94%	92.62%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	84.30%	85.11%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.26%	93.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.06%	93.99%
CHEMBL299	P17252	Protein kinase C alpha	83.84%	98.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.40%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.14%	86.33%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.66%	100.00%
CHEMBL1902	P62942	FK506-binding protein 1A	81.60%	97.05%
CHEMBL2996	Q05655	Protein kinase C delta	81.11%	97.79%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.10%	94.45%
CHEMBL4105838	Q96GG9	DCN1-like protein 1	80.50%	95.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.37%	100.00%

Plants that contains it

• Ajuga reptans

Cross-Links

• PubChem: 163078559
• LOTUS: LTS0109467
• wikiData: Q105153630