[(1S,3R,6R,7R,10R,11S,14S,15R,16R)-14-[(2S,4R,5S,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-7,11-dimethyl-6-(5-oxooxolan-3-yl)-2-oxapentacyclo[8.8.0.01,3.03,7.011,16]octadecan-15-yl] acetate

Details

• Internal ID: 8889e93a-bc01-4b56-a721-4874b5823f2f
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(1S,3R,6R,7R,10R,11S,14S,15R,16R)-14-[(2S,4R,5S,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-7,11-dimethyl-6-(5-oxooxolan-3-yl)-2-oxapentacyclo[8.8.0.01,3.03,7.011,16]octadecan-15-yl] acetate
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C(C2OC(=O)C)CCC45C3CCC6(C4(O5)CCC6C7CC(=O)OC7)C)C)OC)OC8C(C(C(C(O8)CO)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@@H](C[C@@H](O1)O[C@H]2CC[C@]3([C@H]([C@H]2OC(=O)C)CC[C@]45[C@@H]3CC[C@]6([C@]4(O5)CC[C@@H]6C7CC(=O)OC7)C)C)OC)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O
• InChI: InChI=1S/C38H58O14/c1-18-32(51-34-31(44)30(43)29(42)25(16-39)50-34)24(45-5)15-28(47-18)49-23-8-10-35(3)22(33(23)48-19(2)40)6-12-37-26(35)9-11-36(4)21(7-13-38(36,37)52-37)20-14-27(41)46-17-20/h18,20-26,28-34,39,42-44H,6-17H2,1-5H3/t18-,20?,21-,22+,23+,24-,25-,26-,28+,29-,30+,31-,32+,33-,34+,35+,36-,37+,38-/m1/s1
• InChI Key: LYFDVOVSSVKRNP-IBQIYMDASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₅₈O₁₄
• Molecular Weight: 738.90 g/mol
• Exact Mass: 738.38265652 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.75
• H-Bond Acceptor: 14
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5526	55.26%
Caco-2	-	0.8797	87.97%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7455	74.55%
OATP2B1 inhibitior	-	0.8703	87.03%
OATP1B1 inhibitior	+	0.8065	80.65%
OATP1B3 inhibitior	+	0.9586	95.86%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7337	73.37%
P-glycoprotein inhibitior	+	0.7530	75.30%
P-glycoprotein substrate	+	0.6027	60.27%
CYP3A4 substrate	+	0.7488	74.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8831	88.31%
CYP3A4 inhibition	-	0.8258	82.58%
CYP2C9 inhibition	-	0.8127	81.27%
CYP2C19 inhibition	-	0.8178	81.78%
CYP2D6 inhibition	-	0.9455	94.55%
CYP1A2 inhibition	-	0.8834	88.34%
CYP2C8 inhibition	+	0.6066	60.66%
CYP inhibitory promiscuity	-	0.9466	94.66%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6610	66.10%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.9176	91.76%
Skin irritation	-	0.7308	73.08%
Skin corrosion	-	0.9362	93.62%
Ames mutagenesis	-	0.6470	64.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7109	71.09%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.6973	69.73%
skin sensitisation	-	0.9137	91.37%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7074	70.74%
Acute Oral Toxicity (c)	I	0.6001	60.01%
Estrogen receptor binding	+	0.7378	73.78%
Androgen receptor binding	+	0.7552	75.52%
Thyroid receptor binding	-	0.6652	66.52%
Glucocorticoid receptor binding	+	0.6081	60.81%
Aromatase binding	+	0.6635	66.35%
PPAR gamma	+	0.7021	70.21%
Honey bee toxicity	-	0.5814	58.14%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.8846	88.46%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.25%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.62%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	93.43%	100.00%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	93.21%	95.58%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.65%	85.14%
CHEMBL5255	O00206	Toll-like receptor 4	91.16%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.71%	89.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.60%	96.61%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.79%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.75%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.00%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.94%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.31%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.18%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.97%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.57%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	85.54%	95.93%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.54%	91.24%
CHEMBL1871	P10275	Androgen Receptor	84.81%	96.43%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.39%	97.14%
CHEMBL2581	P07339	Cathepsin D	83.69%	98.95%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.63%	97.33%
CHEMBL5028	O14672	ADAM10	82.95%	97.50%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.32%	97.36%
CHEMBL1075317	P61964	WD repeat-containing protein 5	81.28%	96.33%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.24%	94.33%
CHEMBL340	P08684	Cytochrome P450 3A4	80.72%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.58%	97.25%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.49%	96.00%

Plants that contains it

• Parepigynum funingense

Cross-Links

• PubChem: 101725699
• LOTUS: LTS0154702
• wikiData: Q105159276