Digoxigenin bisdigitoxoside

Details

• Internal ID: 39518595-801f-4072-a4c3-d68a0e570248
• 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,12R,13S,14S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-12,14-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(CC(O1)OC2C(OC(CC2O)OC3CCC4(C(C3)CCC5C4CC(C6(C5(CCC6C7=CC(=O)OC7)O)C)O)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]3CC[C@]4([C@@H](C3)CC[C@@H]5[C@@H]4C[C@H]([C@]6([C@@]5(CC[C@@H]6C7=CC(=O)OC7)O)C)O)C)C)O)O
• InChI: InChI=1S/C35H54O11/c1-17-31(40)25(36)14-30(43-17)46-32-18(2)44-29(15-26(32)37)45-21-7-9-33(3)20(12-21)5-6-23-24(33)13-27(38)34(4)22(8-10-35(23,34)41)19-11-28(39)42-16-19/h11,17-18,20-27,29-32,36-38,40-41H,5-10,12-16H2,1-4H3/t17-,18-,20-,21+,22-,23-,24+,25+,26+,27-,29+,30+,31-,32-,33+,34+,35+/m1/s1
• InChI Key: NTSBMKIZRSBFTA-AIDOXSFESA-N
• Popularity: 14 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₄O₁₁
• Molecular Weight: 650.80 g/mol
• Exact Mass: 650.36661253 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 2.34
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

• 5297-05-2
• Digoxigenin-bis(digitoxoside)
• PPY8HS8NF3
• 3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-12,14-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
• Digoxigenin bis-digitoxiside
• Bisdigoxigenin
• Dbis
• UNII-PPY8HS8NF3
• Digoxigenin bis-digitoxose
• Digoxigenin bis-digitoxoside
• CHEMBL1151
• DTXSID80967440
• CHEBI:189931
• DIGOXIGENIN, DIDIGITOXOSIDE
• BDBM231663
• 3-{[2,6-Dideoxy-4-O-(2,6-dideoxyhexopyranosyl)hexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolide
• EINECS 226-143-0
• E98946
• (3beta,5beta,12beta)-3-((2,6-Dideoxy-4-O-(2,6-dideoxy-beta-D-ribo-hexopyranosyl)-beta-D-ribo-hexopyranosyl)oxy)-12,14-dihydroxycard-20(22)-enolide
• 3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-12,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-uran-5-one
• 3beta-((2,6-Dideoxy-4-O-(2,6-dideoxy-beta-D -ribo-hexopyranosyl)-beta-D -ribo-hexopyranosyl)oxy)-12beta,14-dihydroxy-5beta-card-20(22)-enolide
• CARD-20(22)-ENOLIDE, 3-((2,6-DIDEOXY-4-O-(2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL)-.BETA.-D-RIBO-HEXOPYRANOSYL)OXY)-12,14-DIHYDROXY-, (3.BETA.,5.BETA.,12.BETA.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9219	92.19%
Caco-2	-	0.8739	87.39%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8297	82.97%
OATP2B1 inhibitior	-	0.6150	61.50%
OATP1B1 inhibitior	+	0.9462	94.62%
OATP1B3 inhibitior	+	0.9518	95.18%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7023	70.23%
P-glycoprotein inhibitior	+	0.6880	68.80%
P-glycoprotein substrate	+	0.9444	94.44%
CYP3A4 substrate	+	0.5907	59.07%
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	-	0.9882	98.82%
CYP inhibitory promiscuity	-	0.9279	92.79%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5632	56.32%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9357	93.57%
Skin irritation	+	0.5359	53.59%
Skin corrosion	-	0.9388	93.88%
Ames mutagenesis	-	0.5079	50.79%
Human Ether-a-go-go-Related Gene inhibition	+	0.8210	82.10%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.9042	90.42%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.8450	84.50%
Acute Oral Toxicity (c)	I	0.7867	78.67%
Estrogen receptor binding	+	0.7629	76.29%
Androgen receptor binding	+	0.8553	85.53%
Thyroid receptor binding	-	0.7151	71.51%
Glucocorticoid receptor binding	+	0.6326	63.26%
Aromatase binding	+	0.7373	73.73%
PPAR gamma	+	0.6305	63.05%
Honey bee toxicity	-	0.7206	72.06%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9750	97.50%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4096	P04637	Cellular tumor antigen p53	158.5 nM; 79.4 nM	Potency; Potency	via Super-PRED; via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	125.9 nM	Potency	via Super-PRED
CHEMBL1293277	O15118	Niemann-Pick C1 protein	223.9 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	20 nM; 562.3 nM	Potency; Potency	via Super-PRED; via Super-PRED
CHEMBL1293294	P51151	Ras-related protein Rab-9A	223.9 nM	Potency	via Super-PRED
CHEMBL1807	P05023	Sodium/potassium-transporting ATPase alpha-1 chain	290 nM	IC50	via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	794.3 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.73%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.93%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	95.14%	82.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.26%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.17%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.85%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.81%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.46%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.76%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.40%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.25%	89.00%
CHEMBL1871	P10275	Androgen Receptor	85.95%	96.43%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.57%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.36%	99.23%
CHEMBL4040	P28482	MAP kinase ERK2	83.15%	83.82%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.81%	94.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.18%	97.33%

Plants that contains it

• Digitalis lanata
• Digitalis purpurea

Cross-Links

• PubChem: 92999
• NPASS: NPC236993