3-[(3R,10S,13R,14S,16R,17R)-3-[(2R,4S,5S,6R)-5-[(2S,4S,5S,6R)-5-[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-14,16-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: da702dea-09db-4649-a336-73bc9ed74268
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3R,10S,13R,14S,16R,17R)-3-[(2R,4S,5S,6R)-5-[(2S,4S,5S,6R)-5-[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-14,16-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(CC(O1)OC2C(OC(CC2O)OC3C(OC(CC3O)OC4CCC5(C(C4)CCC6C5CCC7(C6(CC(C7C8=CC(=O)OC8)O)O)C)C)C)C)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@@H]2[C@H](O[C@H](C[C@@H]2O)O[C@@H]3[C@H](O[C@H](C[C@@H]3O)O[C@@H]4CC[C@]5(C(C4)CCC6C5CC[C@]7([C@@]6(C[C@H]([C@@H]7C8=CC(=O)OC8)O)O)C)C)C)C)O)O
• InChI: InChI=1S/C41H64O14/c1-19-36(47)27(42)14-33(50-19)54-38-21(3)52-34(16-29(38)44)55-37-20(2)51-32(15-28(37)43)53-24-8-10-39(4)23(13-24)6-7-26-25(39)9-11-40(5)35(22-12-31(46)49-18-22)30(45)17-41(26,40)48/h12,19-21,23-30,32-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19-,20-,21-,23?,24-,25?,26?,27+,28+,29+,30-,32+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1
• InChI Key: LKRDZKPBAOKJBT-VWMORXAASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₄O₁₄
• Molecular Weight: 780.90 g/mol
• Exact Mass: 780.42960671 g/mol
• Topological Polar Surface Area (TPSA): 203.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.22
• H-Bond Acceptor: 14
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9219	92.19%
Caco-2	-	0.9196	91.96%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8297	82.97%
OATP2B1 inhibitior	-	0.8960	89.60%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9518	95.18%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8837	88.37%
P-glycoprotein inhibitior	+	0.7321	73.21%
P-glycoprotein substrate	+	0.8839	88.39%
CYP3A4 substrate	+	0.6861	68.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9026	90.26%
CYP3A4 inhibition	-	0.9279	92.79%
CYP2C9 inhibition	-	0.9196	91.96%
CYP2C19 inhibition	-	0.9385	93.85%
CYP2D6 inhibition	-	0.9359	93.59%
CYP1A2 inhibition	-	0.9261	92.61%
CYP2C8 inhibition	-	0.8837	88.37%
CYP inhibitory promiscuity	-	0.9279	92.79%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5632	56.32%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9444	94.44%
Skin irritation	+	0.5359	53.59%
Skin corrosion	-	0.9388	93.88%
Ames mutagenesis	+	0.5130	51.30%
Human Ether-a-go-go-Related Gene inhibition	+	0.8357	83.57%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.7391	73.91%
skin sensitisation	-	0.9042	90.42%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.8312	83.12%
Acute Oral Toxicity (c)	I	0.7867	78.67%
Estrogen receptor binding	+	0.8763	87.63%
Androgen receptor binding	+	0.8337	83.37%
Thyroid receptor binding	-	0.7888	78.88%
Glucocorticoid receptor binding	+	0.6626	66.26%
Aromatase binding	+	0.7867	78.67%
PPAR gamma	+	0.7551	75.51%
Honey bee toxicity	-	0.6669	66.69%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9750	97.50%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	316.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.37%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.24%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.17%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.21%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.96%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	93.26%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.93%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.69%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.69%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.59%	95.56%
CHEMBL1871	P10275	Androgen Receptor	86.79%	96.43%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.29%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.13%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.08%	99.23%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.97%	96.77%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.56%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.16%	92.94%
CHEMBL2581	P07339	Cathepsin D	84.00%	98.95%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.93%	97.33%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	82.04%	94.78%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.89%	97.14%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.13%	100.00%

Plants that contains it

• Digitalis lanata
• Digitalis purpurea
• Nerium oleander

Cross-Links

• PubChem: 10485386
• NPASS: NPC4949