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

Details

• Internal ID: eee858cb-6e02-4e84-91fb-59f2af7ce506
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: 5-(hydroxymethyl)-2-[1-hydroxy-1-(5,6,14,15,17-pentahydroxy-10,13-dimethyl-1-oxo-3,4,6,7,8,9,11,12,15,16-decahydro-2H-cyclopenta[a]phenanthren-17-yl)ethyl]-4-methyl-2,3-dihydropyran-6-one
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)(C2(CC(C3(C2(CCC4C3CC(C5(C4(C(=O)CCC5)C)O)O)C)O)O)O)O)CO
• SMILES (Isomeric): CC1=C(C(=O)OC(C1)C(C)(C2(CC(C3(C2(CCC4C3CC(C5(C4(C(=O)CCC5)C)O)O)C)O)O)O)O)CO
• InChI: InChI=1S/C28H42O10/c1-14-10-21(38-22(33)15(14)13-29)25(4,34)27(36)12-20(32)28(37)17-11-19(31)26(35)8-5-6-18(30)24(26,3)16(17)7-9-23(27,28)2/h16-17,19-21,29,31-32,34-37H,5-13H2,1-4H3
• InChI Key: QIHKYOJKCDYVEC-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₂O₁₀
• Molecular Weight: 538.60 g/mol
• Exact Mass: 538.27779753 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -0.12
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8209	82.09%
Caco-2	-	0.7578	75.78%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7829	78.29%
OATP2B1 inhibitior	-	0.5686	56.86%
OATP1B1 inhibitior	+	0.8714	87.14%
OATP1B3 inhibitior	+	0.9163	91.63%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5688	56.88%
BSEP inhibitior	+	0.6575	65.75%
P-glycoprotein inhibitior	-	0.5277	52.77%
P-glycoprotein substrate	+	0.5558	55.58%
CYP3A4 substrate	+	0.7170	71.70%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9056	90.56%
CYP3A4 inhibition	-	0.8216	82.16%
CYP2C9 inhibition	-	0.9199	91.99%
CYP2C19 inhibition	-	0.9302	93.02%
CYP2D6 inhibition	-	0.9568	95.68%
CYP1A2 inhibition	-	0.8942	89.42%
CYP2C8 inhibition	+	0.5307	53.07%
CYP inhibitory promiscuity	-	0.9672	96.72%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6907	69.07%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9355	93.55%
Skin irritation	+	0.6327	63.27%
Skin corrosion	-	0.9421	94.21%
Ames mutagenesis	-	0.6436	64.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.3730	37.30%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.6115	61.15%
skin sensitisation	-	0.9270	92.70%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6855	68.55%
Acute Oral Toxicity (c)	III	0.4997	49.97%
Estrogen receptor binding	+	0.7321	73.21%
Androgen receptor binding	+	0.7704	77.04%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6510	65.10%
Aromatase binding	+	0.7623	76.23%
PPAR gamma	+	0.5789	57.89%
Honey bee toxicity	-	0.8417	84.17%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9567	95.67%

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	98.90%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.52%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.40%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	92.95%	97.79%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.49%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.27%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	90.83%	93.04%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.01%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.12%	100.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	87.92%	90.08%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.44%	86.33%
CHEMBL1937	Q92769	Histone deacetylase 2	86.03%	94.75%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.46%	93.03%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.34%	91.11%
CHEMBL259	P32245	Melanocortin receptor 4	85.14%	95.38%
CHEMBL4040	P28482	MAP kinase ERK2	84.96%	83.82%
CHEMBL1871	P10275	Androgen Receptor	84.42%	96.43%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.75%	96.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.47%	92.62%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.09%	93.99%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.90%	94.00%
CHEMBL2581	P07339	Cathepsin D	81.76%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.76%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.71%	97.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.65%	92.94%

Plants that contains it

• Withania coagulans

Cross-Links

• PubChem: 73814448
• LOTUS: LTS0210434
• wikiData: Q104888641