6-Hydroxy-2,16-dimethyl-15-[1-[4-methyl-6-oxo-5-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydropyran-2-yl]ethyl]-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one

Details

• Internal ID: ddbe7bca-c996-4b7a-9df1-39c3dbb847e1
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: 6-hydroxy-2,16-dimethyl-15-[1-[4-methyl-6-oxo-5-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydropyran-2-yl]ethyl]-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C)COC7C(C(C(C(O7)CO)O)O)O
• SMILES (Isomeric): CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C)COC7C(C(C(C(O7)CO)O)O)O
• InChI: InChI=1S/C34H48O11/c1-15-11-22(43-30(41)18(15)14-42-31-29(40)28(39)27(38)23(13-35)44-31)16(2)19-5-6-20-17-12-26-34(45-26)25(37)8-7-24(36)33(34,4)21(17)9-10-32(19,20)3/h7-8,16-17,19-23,25-29,31,35,37-40H,5-6,9-14H2,1-4H3
• InChI Key: WKCJIGSUKSPCKI-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₈O₁₁
• Molecular Weight: 632.70 g/mol
• Exact Mass: 632.31966234 g/mol
• Topological Polar Surface Area (TPSA): 176.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.18
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6537	65.37%
Caco-2	-	0.8695	86.95%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7786	77.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8171	81.71%
OATP1B3 inhibitior	+	0.9083	90.83%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6048	60.48%
BSEP inhibitior	+	0.7554	75.54%
P-glycoprotein inhibitior	+	0.7101	71.01%
P-glycoprotein substrate	+	0.5848	58.48%
CYP3A4 substrate	+	0.7484	74.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8879	88.79%
CYP3A4 inhibition	-	0.9267	92.67%
CYP2C9 inhibition	-	0.7990	79.90%
CYP2C19 inhibition	-	0.8777	87.77%
CYP2D6 inhibition	-	0.9421	94.21%
CYP1A2 inhibition	-	0.8496	84.96%
CYP2C8 inhibition	+	0.6454	64.54%
CYP inhibitory promiscuity	-	0.9421	94.21%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6887	68.87%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9349	93.49%
Skin irritation	-	0.6039	60.39%
Skin corrosion	-	0.9379	93.79%
Ames mutagenesis	-	0.5932	59.32%
Human Ether-a-go-go-Related Gene inhibition	+	0.7431	74.31%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.7106	71.06%
skin sensitisation	-	0.9002	90.02%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.5605	56.05%
Acute Oral Toxicity (c)	I	0.6760	67.60%
Estrogen receptor binding	+	0.7362	73.62%
Androgen receptor binding	+	0.7709	77.09%
Thyroid receptor binding	-	0.6077	60.77%
Glucocorticoid receptor binding	+	0.7076	70.76%
Aromatase binding	+	0.6745	67.45%
PPAR gamma	+	0.6038	60.38%
Honey bee toxicity	-	0.6482	64.82%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9671	96.71%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.21%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.31%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.18%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.81%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.40%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	92.24%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.57%	97.14%
CHEMBL2996	Q05655	Protein kinase C delta	86.95%	97.79%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.77%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.75%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.59%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	84.47%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.42%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.08%	95.89%
CHEMBL5103	Q969S8	Histone deacetylase 10	83.30%	90.08%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.31%	93.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.87%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.60%	97.25%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.24%	96.21%

Plants that contains it

• Physalis longifolia
• Withania somnifera

Cross-Links

• PubChem: 78173488
• LOTUS: LTS0186460
• wikiData: Q105307226