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

Details

• Internal ID: 6c97193d-23c4-42b1-9f10-e9f045301820
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: (1S,2R,5S,6S,7R,9R,11R,12R,15S,16S)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6,12,15-trihydroxy-5-methoxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-3-one
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)(C2(CCC3(C2(CCC4C3CC5C6(C4(C(=O)CC(C6O)OC)C)O5)C)O)O)O)C
• SMILES (Isomeric): CC1=C(C(=O)O[C@H](C1)[C@@](C)([C@@]2(CC[C@@]3([C@@]2(CC[C@H]4[C@H]3C[C@@H]5[C@]6([C@@]4(C(=O)C[C@@H]([C@@H]6O)OC)C)O5)C)O)O)O)C
• InChI: InChI=1S/C29H42O9/c1-14-11-20(37-23(32)15(14)2)26(5,33)28(35)10-9-27(34)17-12-21-29(38-21)22(31)18(36-6)13-19(30)25(29,4)16(17)7-8-24(27,28)3/h16-18,20-22,31,33-35H,7-13H2,1-6H3/t16-,17+,18-,20+,21+,22-,24-,25-,26-,27+,28-,29-/m0/s1
• InChI Key: SZFJLHBQKXQARU-XPHFJZSBSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₂O₉
• Molecular Weight: 534.60 g/mol
• Exact Mass: 534.28288291 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 1.57
• H-Bond Acceptor: 9
• 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	+	0.8534	85.34%
Caco-2	-	0.7234	72.34%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6047	60.47%
OATP2B1 inhibitior	-	0.7132	71.32%
OATP1B1 inhibitior	+	0.8969	89.69%
OATP1B3 inhibitior	+	0.9401	94.01%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7124	71.24%
BSEP inhibitior	+	0.5528	55.28%
P-glycoprotein inhibitior	+	0.5913	59.13%
P-glycoprotein substrate	+	0.5862	58.62%
CYP3A4 substrate	+	0.7345	73.45%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8927	89.27%
CYP3A4 inhibition	-	0.7984	79.84%
CYP2C9 inhibition	-	0.7857	78.57%
CYP2C19 inhibition	-	0.8353	83.53%
CYP2D6 inhibition	-	0.9371	93.71%
CYP1A2 inhibition	-	0.8077	80.77%
CYP2C8 inhibition	+	0.5762	57.62%
CYP inhibitory promiscuity	-	0.9700	97.00%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6226	62.26%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9310	93.10%
Skin irritation	-	0.5593	55.93%
Skin corrosion	-	0.9175	91.75%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4820	48.20%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.6482	64.82%
skin sensitisation	-	0.8464	84.64%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.8626	86.26%
Acute Oral Toxicity (c)	I	0.3261	32.61%
Estrogen receptor binding	+	0.6697	66.97%
Androgen receptor binding	+	0.7772	77.72%
Thyroid receptor binding	-	0.5123	51.23%
Glucocorticoid receptor binding	+	0.7093	70.93%
Aromatase binding	+	0.7757	77.57%
PPAR gamma	+	0.6536	65.36%
Honey bee toxicity	-	0.7660	76.60%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.9604	96.04%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL204	P00734	Thrombin	98.47%	96.01%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.02%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.46%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.87%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.57%	91.11%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	91.38%	97.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.23%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.63%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.18%	86.33%
CHEMBL1902	P62942	FK506-binding protein 1A	89.76%	97.05%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	88.54%	92.68%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	86.65%	97.33%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.90%	93.04%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.83%	91.03%
CHEMBL259	P32245	Melanocortin receptor 4	84.79%	95.38%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.74%	92.94%
CHEMBL1871	P10275	Androgen Receptor	84.54%	96.43%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.22%	94.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.06%	93.03%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.99%	96.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.70%	93.56%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.58%	100.00%
CHEMBL1914	P06276	Butyrylcholinesterase	83.05%	95.00%
CHEMBL2996	Q05655	Protein kinase C delta	82.86%	97.79%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.25%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.01%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	81.56%	94.73%
CHEMBL1907	P15144	Aminopeptidase N	81.36%	93.31%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.88%	100.00%

Plants that contains it

• Physalis minima

Cross-Links

• PubChem: 21607601
• LOTUS: LTS0255508
• wikiData: Q105264099