(1S,2R,6S,7R,9R,11S,12S,16S)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadeca-4,14-dien-3-one

Details

• Internal ID: 6e89cf5e-1da3-44d8-8781-157f72938129
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: (1S,2R,6S,7R,9R,11S,12S,16S)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadeca-4,14-dien-3-one
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)C2=CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C)C
• SMILES (Isomeric): CC1=C(C(=O)O[C@H](C1)[C@@H](C)C2=CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3C[C@@H]5[C@]6([C@@]4(C(=O)C=C[C@@H]6O)C)O5)C)C
• InChI: InChI=1S/C28H36O5/c1-14-12-21(32-25(31)15(14)2)16(3)18-6-7-19-17-13-24-28(33-24)23(30)9-8-22(29)27(28,5)20(17)10-11-26(18,19)4/h6,8-9,16-17,19-21,23-24,30H,7,10-13H2,1-5H3/t16-,17-,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1
• InChI Key: AASNMOOLVFBNQX-YAGAGHGOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₆O₅
• Molecular Weight: 452.60 g/mol
• Exact Mass: 452.25627424 g/mol
• Topological Polar Surface Area (TPSA): 76.10 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 4.30
• H-Bond Acceptor: 5
• 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	+	0.9491	94.91%
Caco-2	-	0.5751	57.51%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7246	72.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8633	86.33%
OATP1B3 inhibitior	+	0.9601	96.01%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6771	67.71%
BSEP inhibitior	+	0.9305	93.05%
P-glycoprotein inhibitior	+	0.7380	73.80%
P-glycoprotein substrate	+	0.5117	51.17%
CYP3A4 substrate	+	0.7041	70.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8911	89.11%
CYP3A4 inhibition	-	0.8703	87.03%
CYP2C9 inhibition	-	0.9136	91.36%
CYP2C19 inhibition	-	0.9247	92.47%
CYP2D6 inhibition	-	0.9559	95.59%
CYP1A2 inhibition	-	0.5494	54.94%
CYP2C8 inhibition	+	0.5418	54.18%
CYP inhibitory promiscuity	-	0.9693	96.93%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5747	57.47%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9614	96.14%
Skin irritation	+	0.5591	55.91%
Skin corrosion	-	0.8890	88.90%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7536	75.36%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.6408	64.08%
skin sensitisation	-	0.8044	80.44%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.7879	78.79%
Acute Oral Toxicity (c)	IV	0.2869	28.69%
Estrogen receptor binding	+	0.8516	85.16%
Androgen receptor binding	+	0.7664	76.64%
Thyroid receptor binding	+	0.5620	56.20%
Glucocorticoid receptor binding	+	0.8086	80.86%
Aromatase binding	+	0.6889	68.89%
PPAR gamma	+	0.6652	66.52%
Honey bee toxicity	-	0.7287	72.87%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9820	98.20%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.79%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	92.39%	97.14%
CHEMBL3359	P21462	Formyl peptide receptor 1	90.04%	93.56%
CHEMBL2581	P07339	Cathepsin D	89.62%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.61%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.10%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.47%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.35%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.62%	100.00%
CHEMBL4444	P04070	Vitamin K-dependent protein C	84.15%	93.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.10%	91.11%
CHEMBL1871	P10275	Androgen Receptor	82.41%	96.43%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.13%	91.07%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.55%	96.61%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.49%	93.03%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.09%	93.04%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.00%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.76%	95.89%

Plants that contains it

• Withania aristata
• Withania somnifera

Cross-Links

• PubChem: 21574482
• LOTUS: LTS0154136
• wikiData: Q104908335