[(3S,5R,8R,9S,10S,12R,13S,14S,16S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,3R,4S,5R)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-12,14-dihydroxy-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-16-yl] acetate

Details

• Internal ID: ee257ce0-5200-4646-b251-44a46c6295c6
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(3S,5R,8R,9S,10S,12R,13S,14S,16S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,3R,4S,5R)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-12,14-dihydroxy-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-16-yl] acetate
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C(C2)CCC4C3CC(C5(C4(CC(C5C6=CC(=O)OC6)OC(=O)C)O)C)O)C)O)OC7C(C(C(CO7)O)OC8C(C(CO8)(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](C2)CC[C@@H]4[C@@H]3C[C@H]([C@]5([C@@]4(C[C@@H]([C@@H]5C6=CC(=O)OC6)OC(=O)C)O)C)O)C)O)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O[C@H]8[C@@H]([C@](CO8)(CO)O)O)O
• InChI: InChI=1S/C41H62O18/c1-18-33(58-36-32(48)34(26(45)15-53-36)59-37-35(49)40(50,16-42)17-54-37)25(44)12-30(55-18)57-22-7-8-38(3)21(10-22)5-6-23-24(38)11-28(46)39(4)31(20-9-29(47)52-14-20)27(56-19(2)43)13-41(23,39)51/h9,18,21-28,30-37,42,44-46,48-51H,5-8,10-17H2,1-4H3/t18-,21-,22+,23-,24+,25+,26-,27+,28-,30+,31+,32-,33-,34+,35+,36+,37+,38+,39-,40-,41+/m1/s1
• InChI Key: ZJSQPBGTLLPEFL-LUUVSMPFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₂O₁₈
• Molecular Weight: 842.90 g/mol
• Exact Mass: 842.39361512 g/mol
• Topological Polar Surface Area (TPSA): 270.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -1.07
• H-Bond Acceptor: 18
• H-Bond Donor: 8
• Rotatable Bonds: 9

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	-	0.8854	88.54%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8375	83.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8910	89.10%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9049	90.49%
P-glycoprotein inhibitior	+	0.7340	73.40%
P-glycoprotein substrate	+	0.8540	85.40%
CYP3A4 substrate	+	0.7314	73.14%
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	+	0.4905	49.05%
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	-	0.9162	91.62%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	+	0.5130	51.30%
Human Ether-a-go-go-Related Gene inhibition	+	0.7758	77.58%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6073	60.73%
skin sensitisation	-	0.9286	92.86%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7554	75.54%
Acute Oral Toxicity (c)	I	0.8759	87.59%
Estrogen receptor binding	+	0.8522	85.22%
Androgen receptor binding	+	0.7853	78.53%
Thyroid receptor binding	-	0.5943	59.43%
Glucocorticoid receptor binding	+	0.6835	68.35%
Aromatase binding	+	0.6852	68.52%
PPAR gamma	+	0.7661	76.61%
Honey bee toxicity	-	0.6132	61.32%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
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	97.88%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.74%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.40%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.29%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	95.19%	82.69%
CHEMBL226	P30542	Adenosine A1 receptor	94.66%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.42%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.61%	86.33%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	91.48%	94.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.20%	96.77%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.86%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.34%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.16%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.24%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.68%	99.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.65%	92.94%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.56%	91.24%
CHEMBL1937	Q92769	Histone deacetylase 2	85.99%	94.75%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.30%	97.36%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	82.55%	97.47%
CHEMBL5028	O14672	ADAM10	82.49%	97.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.99%	94.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.93%	95.71%
CHEMBL3038469	P24941	CDK2/Cyclin A	81.89%	91.38%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.56%	96.00%
CHEMBL2581	P07339	Cathepsin D	81.39%	98.95%
CHEMBL2243	O00519	Anandamide amidohydrolase	81.37%	97.53%
CHEMBL4530	P00488	Coagulation factor XIII	80.83%	96.00%

Plants that contains it

• Ornithogalum nutans

Cross-Links

• PubChem: 162909506
• LOTUS: LTS0241805
• wikiData: Q105378134