3-[(3S,5R,8R,9S,10S,13R,14S,17S)-14-hydroxy-3-[(2R,3R,4R,5S,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-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: 96e796a7-27bf-40be-ae22-f7ec719b1da4
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3S,5R,8R,9S,10S,13R,14S,17S)-14-hydroxy-3-[(2R,3R,4R,5S,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-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)OC2CCC3(C(C2)CCC4C3CCC5(C4(CCC5C6=CC(=O)OC6)O)C)C)O)OC)OC7C(C(C(C(O7)COCC8C(C(C(C(O8)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3CC[C@]5([C@@]4(CC[C@H]5C6=CC(=O)OC6)O)C)C)O)OC)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)COC[C@@H]8[C@H]([C@@H]([C@H]([C@@H](O8)O)O)O)O)O)O)O
• InChI: InChI=1S/C42H66O18/c1-18-35(60-38-33(49)31(47)29(45)26(59-38)17-54-16-25-28(44)30(46)32(48)37(51)58-25)36(53-4)34(50)39(56-18)57-21-7-10-40(2)20(14-21)5-6-24-23(40)8-11-41(3)22(9-12-42(24,41)52)19-13-27(43)55-15-19/h13,18,20-26,28-39,44-52H,5-12,14-17H2,1-4H3/t18-,20-,21+,22+,23+,24-,25-,26-,28-,29-,30+,31+,32-,33-,34-,35+,36-,37-,38+,39+,40+,41-,42+/m1/s1
• InChI Key: NMBJULBBTZKKSQ-SAXIJLEHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₆O₁₈
• Molecular Weight: 859.00 g/mol
• Exact Mass: 858.42491525 g/mol
• Topological Polar Surface Area (TPSA): 273.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -1.24
• H-Bond Acceptor: 18
• H-Bond Donor: 9
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8784	87.84%
Caco-2	-	0.8920	89.20%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7748	77.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8968	89.68%
OATP1B3 inhibitior	+	0.9535	95.35%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8562	85.62%
P-glycoprotein inhibitior	+	0.7384	73.84%
P-glycoprotein substrate	+	0.7474	74.74%
CYP3A4 substrate	+	0.7315	73.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8937	89.37%
CYP3A4 inhibition	-	0.9445	94.45%
CYP2C9 inhibition	-	0.9048	90.48%
CYP2C19 inhibition	-	0.9090	90.90%
CYP2D6 inhibition	-	0.9401	94.01%
CYP1A2 inhibition	-	0.9342	93.42%
CYP2C8 inhibition	+	0.4828	48.28%
CYP inhibitory promiscuity	-	0.9578	95.78%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5631	56.31%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9204	92.04%
Skin irritation	-	0.5890	58.90%
Skin corrosion	-	0.9420	94.20%
Ames mutagenesis	-	0.6824	68.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.8428	84.28%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8942	89.42%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.9322	93.22%
Acute Oral Toxicity (c)	I	0.7402	74.02%
Estrogen receptor binding	+	0.8452	84.52%
Androgen receptor binding	+	0.8062	80.62%
Thyroid receptor binding	-	0.6348	63.48%
Glucocorticoid receptor binding	+	0.6670	66.70%
Aromatase binding	+	0.7155	71.55%
PPAR gamma	+	0.7824	78.24%
Honey bee toxicity	-	0.6111	61.11%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9245	92.45%

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	99.14%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.80%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.30%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.18%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.96%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.55%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.75%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.68%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.46%	96.77%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.63%	97.25%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.23%	92.94%
CHEMBL1871	P10275	Androgen Receptor	89.65%	96.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.88%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.22%	94.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.21%	97.36%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.66%	93.04%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.51%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.45%	95.89%
CHEMBL2581	P07339	Cathepsin D	85.18%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	83.79%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.22%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.75%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.30%	99.23%

Plants that contains it

• Adenium obesum

Cross-Links

• PubChem: 162882117
• LOTUS: LTS0156208
• wikiData: Q105181687