(1S,2R,6S,7R,9R,11S,12S,15R,16S)-15-[(1S)-1-[(2R,4S,5R)-4,5-dimethyl-6-oxooxan-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: c2efda0a-8968-406b-9e82-c6dfa64e3085
• 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-[(1S)-1-[(2R,4S,5R)-4,5-dimethyl-6-oxooxan-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): CC1CC(OC(=O)C1C)C(C)C2CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C
• SMILES (Isomeric): C[C@H]1C[C@@H](OC(=O)[C@@H]1C)[C@@H](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
• InChI: InChI=1S/C28H40O5/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/h8-9,14-21,23-24,30H,6-7,10-13H2,1-5H3/t14-,15+,16-,17-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1
• InChI Key: RXCZYUYRSCOXSS-RUQYMKAZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₀O₅
• Molecular Weight: 456.60 g/mol
• Exact Mass: 456.28757437 g/mol
• Topological Polar Surface Area (TPSA): 76.10 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 4.32
• 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	+	0.9171	91.71%
Caco-2	-	0.6471	64.71%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6882	68.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8365	83.65%
OATP1B3 inhibitior	+	0.9190	91.90%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.7489	74.89%
P-glycoprotein inhibitior	+	0.6094	60.94%
P-glycoprotein substrate	+	0.5262	52.62%
CYP3A4 substrate	+	0.7340	73.40%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8942	89.42%
CYP3A4 inhibition	-	0.8728	87.28%
CYP2C9 inhibition	-	0.9272	92.72%
CYP2C19 inhibition	-	0.9187	91.87%
CYP2D6 inhibition	-	0.9631	96.31%
CYP1A2 inhibition	-	0.5974	59.74%
CYP2C8 inhibition	-	0.6401	64.01%
CYP inhibitory promiscuity	-	0.9831	98.31%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5997	59.97%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9721	97.21%
Skin irritation	+	0.5149	51.49%
Skin corrosion	-	0.8575	85.75%
Ames mutagenesis	-	0.5054	50.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6586	65.86%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.7124	71.24%
skin sensitisation	-	0.8438	84.38%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.5837	58.37%
Acute Oral Toxicity (c)	III	0.2993	29.93%
Estrogen receptor binding	+	0.8259	82.59%
Androgen receptor binding	+	0.7813	78.13%
Thyroid receptor binding	+	0.5895	58.95%
Glucocorticoid receptor binding	+	0.7439	74.39%
Aromatase binding	+	0.6653	66.53%
PPAR gamma	+	0.6139	61.39%
Honey bee toxicity	-	0.7010	70.10%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9745	97.45%

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	94.44%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.27%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.78%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.38%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.47%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.66%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.31%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.75%	100.00%
CHEMBL1871	P10275	Androgen Receptor	85.31%	96.43%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.17%	97.14%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.80%	93.04%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.18%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.33%	82.69%
CHEMBL238	Q01959	Dopamine transporter	82.95%	95.88%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.55%	96.61%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.09%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.70%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.44%	96.77%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.31%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.15%	91.07%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.72%	99.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.51%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	80.33%	90.17%

Plants that contains it

• Vassobia breviflora

Cross-Links

• PubChem: 23266166
• LOTUS: LTS0052916
• wikiData: Q105246938