3-[(3S,5S,8R,9S,10S,13R,14S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

Details

• Internal ID: 31e51287-5003-4f47-9090-bd1bd7feecb3
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3S,5S,8R,9S,10S,13R,14S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2COC(C(C2O)O)OC3C(OC(CC3O)OC4CCC5(C(C4)CCC6C5CCC7(C6(CCC7C8=CC(=O)OC8)O)C)C)C)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2CO[C@H]([C@@H]([C@H]2O)O)O[C@@H]3[C@H](O[C@H](C[C@@H]3O)O[C@H]4CC[C@]5([C@H](C4)CC[C@@H]6[C@@H]5CC[C@]7([C@@]6(CC[C@@H]7C8=CC(=O)OC8)O)C)C)C)O)O)O
• InChI: InChI=1S/C40H62O15/c1-18-30(43)32(45)34(47)37(52-18)54-27-17-50-36(33(46)31(27)44)55-35-19(2)51-29(15-26(35)41)53-22-7-10-38(3)21(14-22)5-6-25-24(38)8-11-39(4)23(9-12-40(25,39)48)20-13-28(42)49-16-20/h13,18-19,21-27,29-37,41,43-48H,5-12,14-17H2,1-4H3/t18-,19+,21-,22-,23+,24-,25+,26-,27+,29-,30-,31-,32+,33+,34+,35+,36-,37-,38-,39+,40-/m0/s1
• InChI Key: ZQFDYTOYDNEECK-LPFBBBNJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₆₂O₁₅
• Molecular Weight: 782.90 g/mol
• Exact Mass: 782.40887127 g/mol
• Topological Polar Surface Area (TPSA): 223.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.80
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8849	88.49%
Caco-2	-	0.9088	90.88%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8225	82.25%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9240	92.40%
OATP1B3 inhibitior	+	0.9510	95.10%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8482	84.82%
P-glycoprotein inhibitior	+	0.7255	72.55%
P-glycoprotein substrate	+	0.8714	87.14%
CYP3A4 substrate	+	0.7149	71.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9026	90.26%
CYP3A4 inhibition	-	0.9502	95.02%
CYP2C9 inhibition	-	0.9264	92.64%
CYP2C19 inhibition	-	0.9255	92.55%
CYP2D6 inhibition	-	0.9373	93.73%
CYP1A2 inhibition	-	0.9291	92.91%
CYP2C8 inhibition	-	0.6801	68.01%
CYP inhibitory promiscuity	-	0.9462	94.62%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5513	55.13%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9369	93.69%
Skin irritation	-	0.5296	52.96%
Skin corrosion	-	0.9382	93.82%
Ames mutagenesis	-	0.5824	58.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.8529	85.29%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.9072	90.72%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.9007	90.07%
Acute Oral Toxicity (c)	I	0.8002	80.02%
Estrogen receptor binding	+	0.8785	87.85%
Androgen receptor binding	+	0.8259	82.59%
Thyroid receptor binding	-	0.7360	73.60%
Glucocorticoid receptor binding	+	0.6482	64.82%
Aromatase binding	+	0.7808	78.08%
PPAR gamma	+	0.7602	76.02%
Honey bee toxicity	-	0.5885	58.85%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9689	96.89%

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	99.16%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.03%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.26%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.31%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.42%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.92%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.56%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.74%	97.36%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.19%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.27%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.25%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.47%	92.94%
CHEMBL3038469	P24941	CDK2/Cyclin A	87.44%	91.38%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.09%	99.23%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	86.86%	97.33%
CHEMBL2581	P07339	Cathepsin D	85.96%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.86%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.23%	90.71%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.35%	82.69%
CHEMBL1871	P10275	Androgen Receptor	84.30%	96.43%
CHEMBL4208	P20618	Proteasome component C5	83.40%	90.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.07%	100.00%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.25%	81.11%

Plants that contains it

• Ornithogalum nutans

Cross-Links

• PubChem: 162953121
• LOTUS: LTS0223713
• wikiData: Q105381425