6,12-dihydroxy-15-[1-[5-(hydroxymethyl)-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: 2baf0b6a-a8c4-460c-a50a-2494788679c2
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: 6,12-dihydroxy-15-[1-[5-(hydroxymethyl)-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): CC(C1CCC2(C1(CCC3C2CC4C5(C3(C(=O)C=CC5O)C)O4)C)O)C6CC=C(C(=O)O6)CO
• SMILES (Isomeric): CC(C1CCC2(C1(CCC3C2CC4C5(C3(C(=O)C=CC5O)C)O4)C)O)C6CC=C(C(=O)O6)CO
• InChI: InChI=1S/C27H36O7/c1-14(19-5-4-15(13-28)23(31)33-19)16-9-11-26(32)18-12-22-27(34-22)21(30)7-6-20(29)25(27,3)17(18)8-10-24(16,26)2/h4,6-7,14,16-19,21-22,28,30,32H,5,8-13H2,1-3H3
• InChI Key: LLAJTJFAKATTTI-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₆O₇
• Molecular Weight: 472.60 g/mol
• Exact Mass: 472.24610348 g/mol
• Topological Polar Surface Area (TPSA): 117.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.08
• 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	-	0.7280	72.80%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7446	74.46%
OATP2B1 inhibitior	-	0.7171	71.71%
OATP1B1 inhibitior	+	0.8372	83.72%
OATP1B3 inhibitior	+	0.9469	94.69%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5796	57.96%
BSEP inhibitior	+	0.8824	88.24%
P-glycoprotein inhibitior	-	0.5411	54.11%
P-glycoprotein substrate	+	0.5638	56.38%
CYP3A4 substrate	+	0.7133	71.33%
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	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.9602	96.02%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5686	56.86%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9690	96.90%
Skin irritation	+	0.5650	56.50%
Skin corrosion	-	0.9359	93.59%
Ames mutagenesis	-	0.5324	53.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.4690	46.90%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8981	89.81%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.6143	61.43%
Acute Oral Toxicity (c)	I	0.5711	57.11%
Estrogen receptor binding	+	0.8196	81.96%
Androgen receptor binding	+	0.7772	77.72%
Thyroid receptor binding	+	0.5901	59.01%
Glucocorticoid receptor binding	+	0.8377	83.77%
Aromatase binding	+	0.7227	72.27%
PPAR gamma	-	0.5280	52.80%
Honey bee toxicity	-	0.7754	77.54%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.73%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.90%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	95.67%	82.69%
CHEMBL2581	P07339	Cathepsin D	95.60%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.97%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.31%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.96%	95.56%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.98%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.79%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.44%	97.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.51%	96.77%
CHEMBL2996	Q05655	Protein kinase C delta	86.57%	97.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.45%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.54%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.47%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	84.11%	90.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.91%	91.07%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.87%	92.62%
CHEMBL4208	P20618	Proteasome component C5	83.46%	90.00%
CHEMBL1937	Q92769	Histone deacetylase 2	83.29%	94.75%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.04%	90.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.33%	99.23%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.30%	92.88%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.72%	85.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.67%	90.71%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.07%	97.28%

Plants that contains it

• Solanum torvum

Cross-Links

• PubChem: 53398686
• NPASS: NPC145382