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

Details

• Internal ID: f3a47a20-c842-44c4-beca-582b296ea35a
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(2R,3R,4S,6R)-6-[(2R,3R,4S,6S)-6-[[(3S,5R,8R,9S,10S,13R,16S,17R)-16-formyloxy-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-[(2R,4S,5R,6R)-5-hydroxy-6-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-methyloxan-3-yl]oxy-3-hydroxy-2-methyloxan-4-yl] acetate
• SMILES (Canonical): CC1C(C(CC(O1)OC2CC(OC(C2OC3CC(C(C(O3)C)O)OC(=O)C)C)OC4CCC5(C(C4)CCC6C5CCC7(C6(CC(C7C8=CC(=O)OC8)OC=O)O)C)C)OC9C(C(C(C(O9)CO)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@H](C[C@H](O1)O[C@H]2C[C@H](O[C@@H]([C@H]2O[C@@H]3C[C@@H]([C@@H]([C@H](O3)C)O)OC(=O)C)C)O[C@H]4CC[C@]5([C@@H](C4)CC[C@@H]6[C@@H]5CC[C@]7(C6(C[C@@H]([C@@H]7C8=CC(=O)OC8)OC=O)O)C)C)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O
• InChI: InChI=1S/C50H76O21/c1-22-41(55)31(66-25(4)53)15-39(64-22)71-46-24(3)65-37(17-33(46)68-38-16-32(42(56)23(2)63-38)69-47-45(59)44(58)43(57)35(19-51)70-47)67-28-9-11-48(5)27(14-28)7-8-30-29(48)10-12-49(6)40(26-13-36(54)61-20-26)34(62-21-52)18-50(30,49)60/h13,21-24,27-35,37-47,51,55-60H,7-12,14-20H2,1-6H3/t22-,23-,24-,27-,28+,29+,30-,31+,32+,33+,34+,35-,37-,38-,39-,40+,41-,42-,43-,44+,45-,46-,47-,48+,49-,50?/m1/s1
• InChI Key: ICEVACCZVSWGIL-RIHNEJIDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₇₆O₂₁
• Molecular Weight: 1013.10 g/mol
• Exact Mass: 1012.48790943 g/mol
• Topological Polar Surface Area (TPSA): 294.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.79
• H-Bond Acceptor: 21
• H-Bond Donor: 7
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8036	80.36%
Caco-2	-	0.8742	87.42%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8375	83.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8833	88.33%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9414	94.14%
P-glycoprotein inhibitior	+	0.7494	74.94%
P-glycoprotein substrate	+	0.7969	79.69%
CYP3A4 substrate	+	0.7414	74.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9029	90.29%
CYP3A4 inhibition	-	0.8550	85.50%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9340	93.40%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9232	92.32%
CYP2C8 inhibition	+	0.6289	62.89%
CYP inhibitory promiscuity	-	0.9425	94.25%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5614	56.14%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9053	90.53%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.5493	54.93%
Human Ether-a-go-go-Related Gene inhibition	+	0.7736	77.36%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6342	63.42%
skin sensitisation	-	0.9286	92.86%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8615	86.15%
Acute Oral Toxicity (c)	I	0.8759	87.59%
Estrogen receptor binding	+	0.8501	85.01%
Androgen receptor binding	+	0.8020	80.20%
Thyroid receptor binding	+	0.5479	54.79%
Glucocorticoid receptor binding	+	0.7409	74.09%
Aromatase binding	+	0.6339	63.39%
PPAR gamma	+	0.8123	81.23%
Honey bee toxicity	-	0.5817	58.17%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9628	96.28%

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	98.62%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.28%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	97.72%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.64%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.34%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.67%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.67%	94.45%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	88.65%	94.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.57%	89.00%
CHEMBL2581	P07339	Cathepsin D	88.35%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.04%	97.25%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.69%	96.21%
CHEMBL5255	O00206	Toll-like receptor 4	86.66%	92.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.04%	95.89%
CHEMBL4208	P20618	Proteasome component C5	83.48%	90.00%
CHEMBL5028	O14672	ADAM10	83.29%	97.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.97%	85.14%
CHEMBL1075317	P61964	WD repeat-containing protein 5	82.76%	96.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.73%	94.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.22%	96.00%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	81.70%	97.53%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.56%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.94%	92.94%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.86%	94.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.39%	92.62%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.02%	91.24%

Plants that contains it

• Digitalis lanata

Cross-Links

• PubChem: 209798
• LOTUS: LTS0047496
• wikiData: Q105110930