(2R)-2-[(1R)-1-[(4S,5R,6R,8R,9S,10R,13S,14R,16S,17R)-4,5,6,14,16,17-hexahydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-4,5-dimethyl-2,3-dihydropyran-6-one

Details

• Internal ID: 275ed930-60ef-41d9-b739-375d901e7efb
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: (2R)-2-[(1R)-1-[(4S,5R,6R,8R,9S,10R,13S,14R,16S,17R)-4,5,6,14,16,17-hexahydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)(C2(C(CC3(C2(CCC4C3CC(C5(C4(C(=O)C=CC5O)C)O)O)C)O)O)O)O)C
• SMILES (Isomeric): CC1=C(C(=O)O[C@H](C1)[C@](C)([C@@]2([C@H](C[C@@]3([C@@]2(CC[C@H]4[C@H]3C[C@H]([C@@]5([C@@]4(C(=O)C=C[C@@H]5O)C)O)O)C)O)O)O)O)C
• InChI: InChI=1S/C28H40O10/c1-13-10-21(38-22(33)14(13)2)25(5,34)28(37)20(32)12-26(35)16-11-19(31)27(36)18(30)7-6-17(29)24(27,4)15(16)8-9-23(26,28)3/h6-7,15-16,18-21,30-32,34-37H,8-12H2,1-5H3/t15-,16+,18-,19+,20-,21+,23-,24-,25+,26+,27-,28-/m0/s1
• InChI Key: AXVGKUKJECSDCD-QWBBZVDASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₀O₁₀
• Molecular Weight: 536.60 g/mol
• Exact Mass: 536.26214747 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -0.35
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8825	88.25%
Caco-2	-	0.7809	78.09%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6991	69.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8752	87.52%
OATP1B3 inhibitior	+	0.9071	90.71%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6124	61.24%
BSEP inhibitior	-	0.4532	45.32%
P-glycoprotein inhibitior	-	0.4922	49.22%
P-glycoprotein substrate	+	0.6280	62.80%
CYP3A4 substrate	+	0.7287	72.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9070	90.70%
CYP3A4 inhibition	-	0.8227	82.27%
CYP2C9 inhibition	-	0.9250	92.50%
CYP2C19 inhibition	-	0.8933	89.33%
CYP2D6 inhibition	-	0.9567	95.67%
CYP1A2 inhibition	-	0.8472	84.72%
CYP2C8 inhibition	+	0.4843	48.43%
CYP inhibitory promiscuity	-	0.9806	98.06%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6250	62.50%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9325	93.25%
Skin irritation	+	0.6575	65.75%
Skin corrosion	-	0.9074	90.74%
Ames mutagenesis	-	0.6536	65.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.3819	38.19%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.6357	63.57%
skin sensitisation	-	0.8347	83.47%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.7133	71.33%
Acute Oral Toxicity (c)	I	0.5312	53.12%
Estrogen receptor binding	+	0.8339	83.39%
Androgen receptor binding	+	0.7829	78.29%
Thyroid receptor binding	+	0.5788	57.88%
Glucocorticoid receptor binding	+	0.6829	68.29%
Aromatase binding	+	0.7820	78.20%
PPAR gamma	+	0.6157	61.57%
Honey bee toxicity	-	0.8320	83.20%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9773	97.73%

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	97.88%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.99%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.29%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.86%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.24%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.59%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.40%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.26%	99.23%
CHEMBL1871	P10275	Androgen Receptor	87.76%	96.43%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.36%	82.69%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.93%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.61%	95.89%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.26%	93.04%
CHEMBL2996	Q05655	Protein kinase C delta	85.04%	97.79%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.95%	91.07%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.77%	91.11%
CHEMBL2581	P07339	Cathepsin D	83.00%	98.95%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.23%	93.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.11%	100.00%

Plants that contains it

• Physalis angulata

Cross-Links

• PubChem: 162875993
• LOTUS: LTS0094487
• wikiData: Q104920835