[(2R,3R,4S,6R)-6-[[(3S,5S,8S,9R,10S,13R,14R,17R)-8,14-dihydroxy-10,13-dimethyl-15-oxo-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,9,11,12,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]-3-[(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-2-methyloxan-4-yl] acetate

Details

• Internal ID: 6b702f27-12e7-43a6-94eb-20ceec280719
• 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-[[(3S,5S,8S,9R,10S,13R,14R,17R)-8,14-dihydroxy-10,13-dimethyl-15-oxo-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,9,11,12,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]-3-[(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-2-methyloxan-4-yl] acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2COC(C(C2O)O)OC3C(OC(CC3OC(=O)C)OC4CCC5(C(C4)CCC6(C5CCC7(C6(C(=O)CC7C8=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]3OC(=O)C)O[C@H]4CC[C@]5([C@H](C4)CC[C@@]6([C@@H]5CC[C@]7([C@@]6(C(=O)C[C@@H]7C8=CC(=O)OC8)O)C)O)C)C)O)O)O
• InChI: InChI=1S/C42H62O18/c1-18-31(46)33(48)35(50)38(56-18)59-26-17-54-37(34(49)32(26)47)60-36-19(2)55-30(15-25(36)57-20(3)43)58-23-7-9-39(4)22(13-23)6-11-41(51)27(39)8-10-40(5)24(14-28(44)42(40,41)52)21-12-29(45)53-16-21/h12,18-19,22-27,30-38,46-52H,6-11,13-17H2,1-5H3/t18-,19+,22-,23-,24+,25-,26+,27+,30-,31-,32-,33+,34+,35+,36+,37-,38-,39-,40+,41-,42+/m0/s1
• InChI Key: LZKRVFPNMOGVMD-ZRRHRCQESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₂O₁₈
• Molecular Weight: 854.90 g/mol
• Exact Mass: 854.39361512 g/mol
• Topological Polar Surface Area (TPSA): 267.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -0.33
• H-Bond Acceptor: 18
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8641	86.41%
Caco-2	-	0.8851	88.51%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8399	83.99%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8832	88.32%
OATP1B3 inhibitior	+	0.9601	96.01%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9369	93.69%
P-glycoprotein inhibitior	+	0.7492	74.92%
P-glycoprotein substrate	+	0.7726	77.26%
CYP3A4 substrate	+	0.7349	73.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9055	90.55%
CYP3A4 inhibition	-	0.9285	92.85%
CYP2C9 inhibition	-	0.9178	91.78%
CYP2C19 inhibition	-	0.9335	93.35%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9356	93.56%
CYP2C8 inhibition	+	0.5591	55.91%
CYP inhibitory promiscuity	-	0.9627	96.27%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5318	53.18%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9152	91.52%
Skin irritation	-	0.5234	52.34%
Skin corrosion	-	0.9338	93.38%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7934	79.34%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.9118	91.18%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.6929	69.29%
Acute Oral Toxicity (c)	I	0.8477	84.77%
Estrogen receptor binding	+	0.8717	87.17%
Androgen receptor binding	+	0.7651	76.51%
Thyroid receptor binding	-	0.5768	57.68%
Glucocorticoid receptor binding	+	0.7537	75.37%
Aromatase binding	+	0.7064	70.64%
PPAR gamma	+	0.8145	81.45%
Honey bee toxicity	-	0.5839	58.39%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9779	97.79%

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	99.15%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.62%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.00%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	94.40%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.91%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.43%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.12%	94.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	89.15%	97.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.97%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.02%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.87%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.76%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	87.27%	91.19%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.30%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.27%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.24%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.59%	97.36%
CHEMBL5028	O14672	ADAM10	81.11%	97.50%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.82%	95.71%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.27%	100.00%

Plants that contains it

• Ornithogalum nutans

Cross-Links

• PubChem: 162843924
• LOTUS: LTS0072300
• wikiData: Q105159955