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

Details

• Internal ID: 676556ac-8e44-4a73-8fa5-38855cedfbff
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: (2R)-5-(hydroxymethyl)-2-[(1R)-1-hydroxy-1-[(5R,6R,8R,9R,10R,13R,14R,17S)-5,6,14-trihydroxy-10,13-dimethyl-1-oxo-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]ethyl]-4-methyl-2,3-dihydropyran-6-one
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)(C2CCC3(C2(CCC4C3CC(C5(C4(C(=O)CCC5)C)O)O)C)O)O)CO
• 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]3C[C@H]([C@@]5([C@@]4(C(=O)CCC5)C)O)O)C)O)O)CO
• InChI: InChI=1S/C28H42O8/c1-15-12-22(36-23(32)16(15)14-29)26(4,33)19-8-11-27(34)18-13-21(31)28(35)9-5-6-20(30)25(28,3)17(18)7-10-24(19,27)2/h17-19,21-22,29,31,33-35H,5-14H2,1-4H3/t17-,18-,19+,21-,22-,24-,25+,26-,27-,28+/m1/s1
• InChI Key: AYSGOPOJGPEGSU-ODBLMDAOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₂O₈
• Molecular Weight: 506.60 g/mol
• Exact Mass: 506.28796829 g/mol
• Topological Polar Surface Area (TPSA): 145.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.79
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9102	91.02%
Caco-2	-	0.6912	69.12%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8225	82.25%
OATP2B1 inhibitior	-	0.5624	56.24%
OATP1B1 inhibitior	+	0.8468	84.68%
OATP1B3 inhibitior	+	0.9236	92.36%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5688	56.88%
BSEP inhibitior	+	0.7835	78.35%
P-glycoprotein inhibitior	-	0.5733	57.33%
P-glycoprotein substrate	-	0.5376	53.76%
CYP3A4 substrate	+	0.7134	71.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9056	90.56%
CYP3A4 inhibition	-	0.7105	71.05%
CYP2C9 inhibition	-	0.9203	92.03%
CYP2C19 inhibition	-	0.9261	92.61%
CYP2D6 inhibition	-	0.9609	96.09%
CYP1A2 inhibition	-	0.8420	84.20%
CYP2C8 inhibition	+	0.5136	51.36%
CYP inhibitory promiscuity	-	0.9720	97.20%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6419	64.19%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.9426	94.26%
Skin irritation	+	0.6729	67.29%
Skin corrosion	-	0.9432	94.32%
Ames mutagenesis	-	0.6090	60.90%
Human Ether-a-go-go-Related Gene inhibition	-	0.4261	42.61%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.6008	60.08%
skin sensitisation	-	0.9260	92.60%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.6146	61.46%
Acute Oral Toxicity (c)	III	0.4395	43.95%
Estrogen receptor binding	+	0.7816	78.16%
Androgen receptor binding	+	0.7687	76.87%
Thyroid receptor binding	-	0.4922	49.22%
Glucocorticoid receptor binding	+	0.7298	72.98%
Aromatase binding	+	0.7852	78.52%
PPAR gamma	+	0.5429	54.29%
Honey bee toxicity	-	0.8281	82.81%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9645	96.45%

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	98.72%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	94.50%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.94%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.65%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.27%	85.14%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.56%	82.69%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.31%	91.11%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	90.56%	93.04%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.35%	99.23%
CHEMBL2581	P07339	Cathepsin D	88.93%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	88.90%	94.75%
CHEMBL5103	Q969S8	Histone deacetylase 10	88.25%	90.08%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.57%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.19%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.54%	93.99%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.25%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.21%	94.00%
CHEMBL4040	P28482	MAP kinase ERK2	82.04%	83.82%
CHEMBL1902	P62942	FK506-binding protein 1A	81.99%	97.05%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.88%	93.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.54%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.23%	96.09%
CHEMBL259	P32245	Melanocortin receptor 4	80.09%	95.38%

Plants that contains it

• Physalis peruviana

Cross-Links

• PubChem: 163090369
• LOTUS: LTS0016873
• wikiData: Q104921351