3-[(3S,5R,8R,9S,10S,11R,13R,14S,17R)-3-[(2S,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-11,14-dihydroxy-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: beb0b90b-adf0-4096-a0f0-93854753e7af
• 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,11R,13R,14S,17R)-3-[(2S,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-11,14-dihydroxy-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)CCC6C5C(CC7(C6(CCC7C8=CC(=O)OC8)O)C)O)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]5[C@@H](C[C@]7([C@@]6(CC[C@@H]7C8=CC(=O)OC8)O)C)O)C)C)O)O)O
• InChI: InChI=1S/C40H62O16/c1-17-30(44)32(46)34(48)37(53-17)55-26-16-51-36(33(47)31(26)45)56-35-18(2)52-28(13-24(35)41)54-21-7-9-38(3)20(12-21)5-6-23-29(38)25(42)14-39(4)22(8-10-40(23,39)49)19-11-27(43)50-15-19/h11,17-18,20-26,28-37,41-42,44-49H,5-10,12-16H2,1-4H3/t17-,18+,20+,21-,22+,23+,24-,25+,26+,28+,29+,30-,31-,32+,33+,34+,35+,36-,37-,38-,39+,40-/m0/s1
• InChI Key: PKHQKJZFVQEEGY-COYMSKIXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₆₂O₁₆
• Molecular Weight: 798.90 g/mol
• Exact Mass: 798.40378589 g/mol
• Topological Polar Surface Area (TPSA): 244.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -0.23
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• 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	-	0.9049	90.49%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8225	82.25%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9230	92.30%
OATP1B3 inhibitior	+	0.9510	95.10%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8879	88.79%
P-glycoprotein inhibitior	+	0.7243	72.43%
P-glycoprotein substrate	+	0.8126	81.26%
CYP3A4 substrate	+	0.7269	72.69%
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	-	0.5951	59.51%
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	-	0.9314	93.14%
Skin irritation	-	0.5296	52.96%
Skin corrosion	-	0.9382	93.82%
Ames mutagenesis	-	0.5770	57.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8559	85.59%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.7717	77.17%
skin sensitisation	-	0.9072	90.72%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8516	85.16%
Acute Oral Toxicity (c)	I	0.8002	80.02%
Estrogen receptor binding	+	0.8759	87.59%
Androgen receptor binding	+	0.8090	80.90%
Thyroid receptor binding	-	0.7116	71.16%
Glucocorticoid receptor binding	+	0.6553	65.53%
Aromatase binding	+	0.7616	76.16%
PPAR gamma	+	0.7645	76.45%
Honey bee toxicity	-	0.5863	58.63%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
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	99.19%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.03%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.60%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.26%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.67%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.51%	97.09%
CHEMBL3038469	P24941	CDK2/Cyclin A	93.32%	91.38%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.80%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.16%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.30%	89.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.98%	97.36%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.38%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.62%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.36%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.71%	95.89%
CHEMBL2581	P07339	Cathepsin D	85.99%	98.95%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	85.78%	97.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.66%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.74%	90.71%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.89%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.83%	82.69%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.69%	95.89%
CHEMBL1871	P10275	Androgen Receptor	80.41%	96.43%
CHEMBL4530	P00488	Coagulation factor XIII	80.26%	96.00%

Plants that contains it

• Ornithogalum nutans

Cross-Links

• PubChem: 162951897
• LOTUS: LTS0030965
• wikiData: Q105210428