[(1S,2R,5R,6S,7R,9R,11S,12S,15R,16R)-6-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-5-methoxy-2-methyl-3-oxo-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-16-yl]methyl acetate

Details

• Internal ID: 0c3ad317-bd12-471c-a5db-cdcb49bd7e8a
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: [(1S,2R,5R,6S,7R,9R,11S,12S,15R,16R)-6-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-5-methoxy-2-methyl-3-oxo-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-16-yl]methyl acetate
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC5C6(C4(C(=O)CC(C6O)OC)C)O5)COC(=O)C)CO
• SMILES (Isomeric): CC1=C(C(=O)O[C@H](C1)[C@@H](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[C@H]([C@@H]6O)OC)C)O5)COC(=O)C)CO
• InChI: InChI=1S/C31H44O9/c1-15-10-23(39-28(36)19(15)13-32)16(2)20-6-7-22-18-11-26-31(40-26)27(35)24(37-5)12-25(34)29(31,4)21(18)8-9-30(20,22)14-38-17(3)33/h16,18,20-24,26-27,32,35H,6-14H2,1-5H3/t16-,18+,20+,21-,22-,23+,24+,26+,27-,29-,30-,31-/m0/s1
• InChI Key: GZCABIONXWKRNY-QAICGRTPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₄O₉
• Molecular Weight: 560.70 g/mol
• Exact Mass: 560.29853298 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.75
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8730	87.30%
Caco-2	-	0.7870	78.70%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7696	76.96%
OATP2B1 inhibitior	-	0.7071	70.71%
OATP1B1 inhibitior	+	0.8346	83.46%
OATP1B3 inhibitior	+	0.9287	92.87%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7021	70.21%
BSEP inhibitior	+	0.9194	91.94%
P-glycoprotein inhibitior	+	0.6992	69.92%
P-glycoprotein substrate	+	0.6743	67.43%
CYP3A4 substrate	+	0.7402	74.02%
CYP2C9 substrate	-	0.8370	83.70%
CYP2D6 substrate	-	0.8944	89.44%
CYP3A4 inhibition	-	0.8800	88.00%
CYP2C9 inhibition	-	0.8256	82.56%
CYP2C19 inhibition	-	0.8757	87.57%
CYP2D6 inhibition	-	0.9481	94.81%
CYP1A2 inhibition	-	0.8346	83.46%
CYP2C8 inhibition	+	0.6444	64.44%
CYP inhibitory promiscuity	-	0.9264	92.64%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6284	62.84%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9403	94.03%
Skin irritation	-	0.6236	62.36%
Skin corrosion	-	0.9395	93.95%
Ames mutagenesis	-	0.5602	56.02%
Human Ether-a-go-go-Related Gene inhibition	-	0.5180	51.80%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.5092	50.92%
skin sensitisation	-	0.8995	89.95%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.7304	73.04%
Acute Oral Toxicity (c)	I	0.6987	69.87%
Estrogen receptor binding	+	0.7717	77.17%
Androgen receptor binding	+	0.7597	75.97%
Thyroid receptor binding	-	0.6078	60.78%
Glucocorticoid receptor binding	+	0.7539	75.39%
Aromatase binding	+	0.7453	74.53%
PPAR gamma	+	0.6409	64.09%
Honey bee toxicity	-	0.6890	68.90%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9432	94.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.40%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	95.37%	97.79%
CHEMBL204	P00734	Thrombin	95.25%	96.01%
CHEMBL1937	Q92769	Histone deacetylase 2	92.09%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.68%	97.09%
CHEMBL2581	P07339	Cathepsin D	91.52%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.41%	91.11%
CHEMBL5103	Q969S8	Histone deacetylase 10	89.60%	90.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.13%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.67%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.12%	95.56%
CHEMBL299	P17252	Protein kinase C alpha	86.98%	98.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.92%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.71%	95.89%
CHEMBL3837	P07711	Cathepsin L	85.09%	96.61%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.92%	97.14%
CHEMBL5028	O14672	ADAM10	84.85%	97.50%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	84.19%	91.65%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.19%	85.14%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.09%	93.03%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.94%	82.69%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.89%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.19%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.90%	92.62%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.61%	91.07%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.92%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.90%	95.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.88%	93.04%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.67%	100.00%
CHEMBL3310	Q96DB2	Histone deacetylase 11	80.05%	88.56%

Plants that contains it

• Iochroma gesnerioides

Cross-Links

• PubChem: 162869009
• LOTUS: LTS0001720
• wikiData: Q105024329