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

Details

• Internal ID: 9b5bba6e-8edc-4308-ae77-b304262a38d2
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: 6,15-dihydroxy-15-[1-[5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-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)C2(CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C)O)CO
• SMILES (Isomeric): CC1=C(C(=O)OC(C1)C(C)C2(CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C)O)CO
• InChI: InChI=1S/C28H38O7/c1-14-11-20(34-24(32)17(14)13-29)15(2)27(33)10-8-18-16-12-23-28(35-23)22(31)6-5-21(30)26(28,4)19(16)7-9-25(18,27)3/h5-6,15-16,18-20,22-23,29,31,33H,7-13H2,1-4H3
• InChI Key: HLZVPWRVYKJCMY-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₈O₇
• Molecular Weight: 486.60 g/mol
• Exact Mass: 486.26175355 g/mol
• Topological Polar Surface Area (TPSA): 117.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.47
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9375	93.75%
Caco-2	-	0.7241	72.41%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7446	74.46%
OATP2B1 inhibitior	-	0.7147	71.47%
OATP1B1 inhibitior	+	0.8143	81.43%
OATP1B3 inhibitior	+	0.9469	94.69%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5796	57.96%
BSEP inhibitior	+	0.8828	88.28%
P-glycoprotein inhibitior	-	0.4389	43.89%
P-glycoprotein substrate	+	0.5847	58.47%
CYP3A4 substrate	+	0.7120	71.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8961	89.61%
CYP3A4 inhibition	-	0.6949	69.49%
CYP2C9 inhibition	-	0.8257	82.57%
CYP2C19 inhibition	-	0.9233	92.33%
CYP2D6 inhibition	-	0.9540	95.40%
CYP1A2 inhibition	-	0.8616	86.16%
CYP2C8 inhibition	+	0.5212	52.12%
CYP inhibitory promiscuity	-	0.9602	96.02%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5686	56.86%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9523	95.23%
Skin irritation	+	0.5650	56.50%
Skin corrosion	-	0.9359	93.59%
Ames mutagenesis	-	0.5732	57.32%
Human Ether-a-go-go-Related Gene inhibition	-	0.4478	44.78%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.8981	89.81%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.6279	62.79%
Acute Oral Toxicity (c)	I	0.5711	57.11%
Estrogen receptor binding	+	0.8120	81.20%
Androgen receptor binding	+	0.7894	78.94%
Thyroid receptor binding	+	0.5859	58.59%
Glucocorticoid receptor binding	+	0.7945	79.45%
Aromatase binding	+	0.7367	73.67%
PPAR gamma	+	0.5841	58.41%
Honey bee toxicity	-	0.7262	72.62%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9586	95.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.70%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.14%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.68%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.95%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.82%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.72%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.03%	82.69%
CHEMBL4072	P07858	Cathepsin B	89.10%	93.67%
CHEMBL2996	Q05655	Protein kinase C delta	88.59%	97.79%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.03%	97.14%
CHEMBL5103	Q969S8	Histone deacetylase 10	86.55%	90.08%
CHEMBL1937	Q92769	Histone deacetylase 2	85.37%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.75%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.22%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.03%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.37%	95.89%
CHEMBL1914	P06276	Butyrylcholinesterase	81.00%	95.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.73%	93.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.44%	86.33%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.22%	93.03%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.21%	90.71%

Plants that contains it

• Withania somnifera

Cross-Links

• PubChem: 85435491
• LOTUS: LTS0056132
• wikiData: Q104888961