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

Details

• Internal ID: ce89be19-08ce-41e4-b8cf-59a0bf8c53a7
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: 4-(hydroxymethyl)-2-[1-hydroxy-1-(6,14,17-trihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,15,16-octahydrocyclopenta[a]phenanthren-17-yl)ethyl]-5-methyl-2,3-dihydropyran-6-one
• SMILES (Canonical): CC1=C(CC(OC1=O)C(C)(C2(CCC3(C2(CCC4C3CC(C5=CC=CC(=O)C45C)O)C)O)O)O)CO
• SMILES (Isomeric): CC1=C(CC(OC1=O)C(C)(C2(CCC3(C2(CCC4C3CC(C5=CC=CC(=O)C45C)O)C)O)O)O)CO
• InChI: InChI=1S/C28H38O8/c1-15-16(14-29)12-22(36-23(15)32)26(4,33)28(35)11-10-27(34)19-13-20(30)18-6-5-7-21(31)25(18,3)17(19)8-9-24(27,28)2/h5-7,17,19-20,22,29-30,33-35H,8-14H2,1-4H3
• InChI Key: IQBIRJGFMZVQJE-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₈O₈
• Molecular Weight: 502.60 g/mol
• Exact Mass: 502.25666817 g/mol
• Topological Polar Surface Area (TPSA): 145.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 1.49
• 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	+	0.8651	86.51%
Caco-2	-	0.7536	75.36%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8215	82.15%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8835	88.35%
OATP1B3 inhibitior	+	0.8868	88.68%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5438	54.38%
BSEP inhibitior	+	0.7747	77.47%
P-glycoprotein inhibitior	-	0.4515	45.15%
P-glycoprotein substrate	+	0.6451	64.51%
CYP3A4 substrate	+	0.7212	72.12%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9074	90.74%
CYP3A4 inhibition	-	0.7935	79.35%
CYP2C9 inhibition	-	0.9249	92.49%
CYP2C19 inhibition	-	0.9334	93.34%
CYP2D6 inhibition	-	0.9552	95.52%
CYP1A2 inhibition	-	0.8935	89.35%
CYP2C8 inhibition	+	0.6061	60.61%
CYP inhibitory promiscuity	-	0.9669	96.69%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6405	64.05%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9521	95.21%
Skin irritation	+	0.6554	65.54%
Skin corrosion	-	0.9384	93.84%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6750	67.50%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.9323	93.23%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.5714	57.14%
Acute Oral Toxicity (c)	III	0.6536	65.36%
Estrogen receptor binding	+	0.8590	85.90%
Androgen receptor binding	+	0.7498	74.98%
Thyroid receptor binding	+	0.6330	63.30%
Glucocorticoid receptor binding	+	0.7617	76.17%
Aromatase binding	+	0.7678	76.78%
PPAR gamma	+	0.5883	58.83%
Honey bee toxicity	-	0.7905	79.05%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9614	96.14%

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	99.08%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.75%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.76%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.97%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.29%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.84%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.73%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.50%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.80%	86.33%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.29%	82.69%
CHEMBL1871	P10275	Androgen Receptor	86.36%	96.43%
CHEMBL220	P22303	Acetylcholinesterase	85.48%	94.45%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	84.96%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.75%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.74%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.55%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.72%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	80.80%	97.79%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.35%	91.07%
CHEMBL230	P35354	Cyclooxygenase-2	80.23%	89.63%

Plants that contains it

• Physalis viscosa

Cross-Links

• PubChem: 73833824
• LOTUS: LTS0251049
• wikiData: Q105117642