3-[(3S,5S,8R,9S,10S,13R,14S,15R,16S,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-14,15,16-trihydroxy-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: 1f10d181-e5ab-48fe-a1b5-10d4be7ed87e
• 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,15R,16S,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-14,15,16-trihydroxy-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(C(C(C7C8=CC(=O)OC8)O)O)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([C@@H]([C@H]([C@@H]7C8=CC(=O)OC8)O)O)O)C)C)C)O)O)O
• InChI: InChI=1S/C40H62O17/c1-16-28(43)31(46)33(48)37(54-16)56-24-15-52-36(32(47)29(24)44)57-34-17(2)53-26(13-23(34)41)55-20-7-9-38(3)19(12-20)5-6-22-21(38)8-10-39(4)27(18-11-25(42)51-14-18)30(45)35(49)40(22,39)50/h11,16-17,19-24,26-37,41,43-50H,5-10,12-15H2,1-4H3/t16-,17+,19-,20-,21-,22+,23-,24+,26-,27-,28-,29-,30-,31+,32+,33+,34+,35+,36-,37-,38-,39+,40+/m0/s1
• InChI Key: FBNZRVSNKMCVFD-ABGOPOASSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₆₂O₁₇
• Molecular Weight: 814.90 g/mol
• Exact Mass: 814.39870051 g/mol
• Topological Polar Surface Area (TPSA): 264.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -1.26
• H-Bond Acceptor: 17
• H-Bond Donor: 9
• 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	-	0.9027	90.27%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8225	82.25%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8981	89.81%
OATP1B3 inhibitior	+	0.9510	95.10%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8475	84.75%
P-glycoprotein inhibitior	+	0.7274	72.74%
P-glycoprotein substrate	+	0.8037	80.37%
CYP3A4 substrate	+	0.7309	73.09%
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	+	0.4773	47.73%
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	-	0.9285	92.85%
Skin irritation	-	0.5296	52.96%
Skin corrosion	-	0.9382	93.82%
Ames mutagenesis	-	0.5424	54.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.8477	84.77%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.6699	66.99%
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	-	0.8743	87.43%
Acute Oral Toxicity (c)	I	0.8002	80.02%
Estrogen receptor binding	+	0.8722	87.22%
Androgen receptor binding	+	0.7985	79.85%
Thyroid receptor binding	-	0.6705	67.05%
Glucocorticoid receptor binding	+	0.6676	66.76%
Aromatase binding	+	0.7573	75.73%
PPAR gamma	+	0.7760	77.60%
Honey bee toxicity	-	0.5859	58.59%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
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	98.54%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.83%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.30%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.02%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.00%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.88%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.43%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.27%	94.00%
CHEMBL4208	P20618	Proteasome component C5	89.83%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.27%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.83%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.16%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.44%	97.36%
CHEMBL2581	P07339	Cathepsin D	86.11%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.28%	92.94%
CHEMBL1937	Q92769	Histone deacetylase 2	84.03%	94.75%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.03%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.56%	95.89%
CHEMBL1871	P10275	Androgen Receptor	81.99%	96.43%
CHEMBL4530	P00488	Coagulation factor XIII	81.72%	96.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.30%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.28%	95.89%
CHEMBL5028	O14672	ADAM10	80.15%	97.50%

Plants that contains it

• Ornithogalum nutans

Cross-Links

• PubChem: 162934613
• LOTUS: LTS0233900
• wikiData: Q104992755