(2R)-2-[(1S)-1-hydroxy-1-[(6S,8R,9S,10R,13S,14R,17S)-6,14,17-trihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,15,16-octahydrocyclopenta[a]phenanthren-17-yl]ethyl]-4,5-dimethyl-2,3-dihydropyran-6-one

Details

• Internal ID: fa981cb3-cf92-4051-9515-0e6f9261c777
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: (2R)-2-[(1S)-1-hydroxy-1-[(6S,8R,9S,10R,13S,14R,17S)-6,14,17-trihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,15,16-octahydrocyclopenta[a]phenanthren-17-yl]ethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)(C2(CCC3(C2(CCC4C3CC(C5=CC=CC(=O)C45C)O)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](C5=CC=CC(=O)[C@]45C)O)C)O)O)O)C
• InChI: InChI=1S/C28H38O7/c1-15-13-22(35-23(31)16(15)2)26(5,32)28(34)12-11-27(33)19-14-20(29)18-7-6-8-21(30)25(18,4)17(19)9-10-24(27,28)3/h6-8,17,19-20,22,29,32-34H,9-14H2,1-5H3/t17-,19+,20-,22+,24-,25+,26-,27+,28-/m0/s1
• InChI Key: IBJZGHYOMSKIJB-IBXPYDNGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₈O₇
• Molecular Weight: 486.60 g/mol
• Exact Mass: 486.26175355 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 2.51
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9129	91.29%
Caco-2	-	0.6872	68.72%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7508	75.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8932	89.32%
OATP1B3 inhibitior	+	0.9021	90.21%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6124	61.24%
BSEP inhibitior	+	0.8682	86.82%
P-glycoprotein inhibitior	-	0.4812	48.12%
P-glycoprotein substrate	+	0.5831	58.31%
CYP3A4 substrate	+	0.7127	71.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9070	90.70%
CYP3A4 inhibition	-	0.8102	81.02%
CYP2C9 inhibition	-	0.9188	91.88%
CYP2C19 inhibition	-	0.9084	90.84%
CYP2D6 inhibition	-	0.9525	95.25%
CYP1A2 inhibition	-	0.8466	84.66%
CYP2C8 inhibition	+	0.5522	55.22%
CYP inhibitory promiscuity	-	0.9794	97.94%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5917	59.17%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.9424	94.24%
Skin irritation	+	0.6663	66.63%
Skin corrosion	-	0.9078	90.78%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7185	71.85%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.7074	70.74%
skin sensitisation	-	0.8497	84.97%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.6344	63.44%
Acute Oral Toxicity (c)	I	0.4263	42.63%
Estrogen receptor binding	+	0.8518	85.18%
Androgen receptor binding	+	0.7568	75.68%
Thyroid receptor binding	+	0.6461	64.61%
Glucocorticoid receptor binding	+	0.7647	76.47%
Aromatase binding	+	0.7975	79.75%
PPAR gamma	+	0.5912	59.12%
Honey bee toxicity	-	0.7779	77.79%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9797	97.97%

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	99.04%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.62%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.73%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.07%	91.11%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.29%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.17%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.13%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.95%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.56%	89.00%
CHEMBL220	P22303	Acetylcholinesterase	86.48%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.47%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.87%	95.89%
CHEMBL1871	P10275	Androgen Receptor	84.27%	96.43%
CHEMBL1914	P06276	Butyrylcholinesterase	83.72%	95.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.20%	93.04%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.00%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.15%	82.69%

Plants that contains it

• Physalis viscosa

Cross-Links

• PubChem: 127047502
• LOTUS: LTS0157872
• wikiData: Q105036542