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

Details

• Internal ID: 6f3e3829-da97-407e-9b90-528886386f53
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: (2R)-2-[(1R)-1-[(4S,8R,9S,10R,13R,14R,17S)-4,14-dihydroxy-10,13-dimethyl-1-oxo-7,8,9,11,12,15,16,17-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)(C2CCC3(C2(CCC4C3CC=C5C4(C(=O)C=CC5O)C)C)O)O)C
• SMILES (Isomeric): CC1=C(C(=O)O[C@H](C1)[C@@](C)([C@H]2CC[C@@]3([C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(C(=O)C=C[C@@H]5O)C)C)O)O)C
• InChI: InChI=1S/C28H38O6/c1-15-14-23(34-24(31)16(15)2)27(5,32)21-11-13-28(33)18-6-7-19-20(29)8-9-22(30)26(19,4)17(18)10-12-25(21,28)3/h7-9,17-18,20-21,23,29,32-33H,6,10-14H2,1-5H3/t17-,18+,20-,21-,23+,25+,26+,27+,28+/m0/s1
• InChI Key: HQTMLKNKTSIYDB-PDNGWDEOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₈O₆
• Molecular Weight: 470.60 g/mol
• Exact Mass: 470.26683893 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 3.40
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9766	97.66%
Caco-2	-	0.6361	63.61%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8111	81.11%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8754	87.54%
OATP1B3 inhibitior	+	0.9151	91.51%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5876	58.76%
BSEP inhibitior	+	0.8475	84.75%
P-glycoprotein inhibitior	+	0.5986	59.86%
P-glycoprotein substrate	-	0.5550	55.50%
CYP3A4 substrate	+	0.7232	72.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9113	91.13%
CYP3A4 inhibition	-	0.7938	79.38%
CYP2C9 inhibition	-	0.9347	93.47%
CYP2C19 inhibition	-	0.9375	93.75%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.8113	81.13%
CYP2C8 inhibition	+	0.5235	52.35%
CYP inhibitory promiscuity	-	0.9664	96.64%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5919	59.19%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.9595	95.95%
Skin irritation	+	0.7150	71.50%
Skin corrosion	-	0.9155	91.55%
Ames mutagenesis	-	0.6437	64.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4526	45.26%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.5181	51.81%
skin sensitisation	-	0.8145	81.45%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5358	53.58%
Acute Oral Toxicity (c)	IV	0.4726	47.26%
Estrogen receptor binding	+	0.8416	84.16%
Androgen receptor binding	+	0.7385	73.85%
Thyroid receptor binding	+	0.6318	63.18%
Glucocorticoid receptor binding	+	0.8359	83.59%
Aromatase binding	+	0.7803	78.03%
PPAR gamma	+	0.5392	53.92%
Honey bee toxicity	-	0.8423	84.23%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9837	98.37%

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	98.36%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.97%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.41%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.74%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.53%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.77%	97.14%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.24%	93.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.70%	95.89%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.13%	93.04%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.69%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.26%	91.07%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	82.56%	90.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.27%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.24%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.21%	99.23%
CHEMBL1871	P10275	Androgen Receptor	80.90%	96.43%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.47%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	80.17%	94.73%

Plants that contains it

• Withania somnifera

Cross-Links

• PubChem: 163190953
• LOTUS: LTS0034057
• wikiData: Q105032430