(1S,2R,6S,7R,9R,11S,12S,15R,16S)-15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one

Details

• Internal ID: cc7dbfa0-e359-430d-9aff-07cff4cecf1e
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: (1S,2R,6S,7R,9R,11S,12S,15R,16S)-15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-6-hydroxy-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)C2CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C)C
• SMILES (Isomeric): CC1=C(C(=O)OC(C1)C(C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3C[C@@H]5[C@]6([C@@]4(C(=O)C=C[C@@H]6O)C)O5)C)C
• InChI: InChI=1S/C28H38O5/c1-14-12-21(32-25(31)15(14)2)16(3)18-6-7-19-17-13-24-28(33-24)23(30)9-8-22(29)27(28,5)20(17)10-11-26(18,19)4/h8-9,16-21,23-24,30H,6-7,10-13H2,1-5H3/t16?,17-,18+,19-,20-,21?,23-,24+,26+,27-,28+/m0/s1
• InChI Key: HBFRBCZKKTVLPR-HSUQEJLWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₈O₅
• Molecular Weight: 454.60 g/mol
• Exact Mass: 454.27192431 g/mol
• Topological Polar Surface Area (TPSA): 76.10 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.38
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9491	94.91%
Caco-2	-	0.6159	61.59%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7246	72.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8407	84.07%
OATP1B3 inhibitior	+	0.9601	96.01%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6771	67.71%
BSEP inhibitior	+	0.9009	90.09%
P-glycoprotein inhibitior	+	0.6785	67.85%
P-glycoprotein substrate	+	0.5332	53.32%
CYP3A4 substrate	+	0.7370	73.70%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8911	89.11%
CYP3A4 inhibition	-	0.8703	87.03%
CYP2C9 inhibition	-	0.9136	91.36%
CYP2C19 inhibition	-	0.9247	92.47%
CYP2D6 inhibition	-	0.9559	95.59%
CYP1A2 inhibition	-	0.5494	54.94%
CYP2C8 inhibition	+	0.4611	46.11%
CYP inhibitory promiscuity	-	0.9693	96.93%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5747	57.47%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9674	96.74%
Skin irritation	+	0.5591	55.91%
Skin corrosion	-	0.8890	88.90%
Ames mutagenesis	-	0.5354	53.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7116	71.16%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.6749	67.49%
skin sensitisation	-	0.8044	80.44%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.6331	63.31%
Acute Oral Toxicity (c)	IV	0.2869	28.69%
Estrogen receptor binding	+	0.8349	83.49%
Androgen receptor binding	+	0.7774	77.74%
Thyroid receptor binding	+	0.5974	59.74%
Glucocorticoid receptor binding	+	0.7921	79.21%
Aromatase binding	+	0.7179	71.79%
PPAR gamma	+	0.6509	65.09%
Honey bee toxicity	-	0.7463	74.63%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9820	98.20%

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	94.56%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.88%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.51%	97.14%
CHEMBL2581	P07339	Cathepsin D	88.02%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.22%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.55%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.43%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.23%	85.14%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.17%	93.04%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.49%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.42%	93.56%
CHEMBL221	P23219	Cyclooxygenase-1	83.26%	90.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.87%	90.71%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.71%	97.25%
CHEMBL1871	P10275	Androgen Receptor	82.61%	96.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.50%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.94%	96.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.79%	82.69%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.18%	91.07%

Plants that contains it

• Solanum torvum

Cross-Links

• PubChem: 10161347
• NPASS: NPC174042