(1R,2R,7S,9R,11S,12R,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-ene-3,6-dione

Details

• Internal ID: c4a631b6-f67d-4268-8813-400b8296ead5
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: (1R,2R,7S,9R,11S,12R,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-ene-3,6-dione
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)(C2CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6=O)C)O5)C)O)C
• SMILES (Isomeric): CC1=C(C(=O)O[C@H](C1)[C@@](C)([C@H]2CC[C@H]3[C@@]2(CC[C@@H]4[C@H]3C[C@@H]5[C@]6([C@@]4(C(=O)C=CC6=O)C)O5)C)O)C
• InChI: InChI=1S/C28H36O6/c1-14-12-22(33-24(31)15(14)2)27(5,32)19-7-6-17-16-13-23-28(34-23)21(30)9-8-20(29)26(28,4)18(16)10-11-25(17,19)3/h8-9,16-19,22-23,32H,6-7,10-13H2,1-5H3/t16-,17+,18+,19-,22+,23+,25-,26-,27+,28+/m0/s1
• InChI Key: XLPMOKAMOKNAMA-PJRMTJMLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₆O₆
• Molecular Weight: 468.60 g/mol
• Exact Mass: 468.25118886 g/mol
• Topological Polar Surface Area (TPSA): 93.20 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.70
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9622	96.22%
Caco-2	-	0.5863	58.63%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7534	75.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9016	90.16%
OATP1B3 inhibitior	+	0.8812	88.12%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6874	68.74%
BSEP inhibitior	+	0.9013	90.13%
P-glycoprotein inhibitior	+	0.7219	72.19%
P-glycoprotein substrate	-	0.5657	56.57%
CYP3A4 substrate	+	0.7405	74.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8995	89.95%
CYP3A4 inhibition	-	0.8486	84.86%
CYP2C9 inhibition	-	0.8713	87.13%
CYP2C19 inhibition	-	0.8811	88.11%
CYP2D6 inhibition	-	0.9568	95.68%
CYP1A2 inhibition	-	0.6064	60.64%
CYP2C8 inhibition	+	0.5556	55.56%
CYP inhibitory promiscuity	-	0.9710	97.10%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6035	60.35%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9458	94.58%
Skin irritation	+	0.5338	53.38%
Skin corrosion	-	0.8962	89.62%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7086	70.86%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.6033	60.33%
skin sensitisation	-	0.8096	80.96%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.6034	60.34%
Acute Oral Toxicity (c)	IV	0.3202	32.02%
Estrogen receptor binding	+	0.7892	78.92%
Androgen receptor binding	+	0.7859	78.59%
Thyroid receptor binding	+	0.6084	60.84%
Glucocorticoid receptor binding	+	0.8349	83.49%
Aromatase binding	+	0.8236	82.36%
PPAR gamma	+	0.6751	67.51%
Honey bee toxicity	-	0.8543	85.43%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.9845	98.45%

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	95.52%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.30%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.03%	95.56%
CHEMBL230	P35354	Cyclooxygenase-2	90.59%	89.63%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.14%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	88.71%	93.04%
CHEMBL1871	P10275	Androgen Receptor	88.70%	96.43%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.15%	97.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.07%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.79%	99.23%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.41%	93.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.53%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.38%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.38%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	82.16%	94.73%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.04%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	81.37%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.29%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.79%	82.69%

Plants that contains it

• Withania somnifera

Cross-Links

• PubChem: 162882388
• LOTUS: LTS0241349
• wikiData: Q105330172