Card-20(22)-enolide, 3-[(O-beta-D-glucopyranosyl-(1-->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy]-14-hydroxy-, (3beta,5beta)-

Details

• Internal ID: c820713e-08e2-4e9a-83fb-356889cbe315
• 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,13R,14S,17R)-14-hydroxy-3-[(2R,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-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)OC2CCC3(C(C2)CCC4C3CCC5(C4(CCC5C6=CC(=O)OC6)O)C)C)O)OC7CC(C(C(O7)C)OC8CC(C(C(O8)C)OC9C(C(C(C(O9)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3CC[C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)C)O)O[C@H]7C[C@@H]([C@@H]([C@H](O7)C)O[C@H]8C[C@@H]([C@@H]([C@H](O8)C)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O
• InChI: InChI=1S/C47H74O18/c1-21-41(63-36-17-31(50)42(22(2)59-36)64-37-18-32(51)43(23(3)60-37)65-44-40(55)39(54)38(53)33(19-48)62-44)30(49)16-35(58-21)61-26-8-11-45(4)25(15-26)6-7-29-28(45)9-12-46(5)27(10-13-47(29,46)56)24-14-34(52)57-20-24/h14,21-23,25-33,35-44,48-51,53-56H,6-13,15-20H2,1-5H3/t21-,22-,23-,25-,26+,27-,28+,29-,30+,31+,32+,33-,35+,36+,37+,38-,39+,40-,41-,42-,43-,44+,45+,46-,47+/m1/s1
• InChI Key: BZJBLHNKKRCQEQ-ZFCLPHBQSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₄O₁₈
• Molecular Weight: 927.10 g/mol
• Exact Mass: 926.48751551 g/mol
• Topological Polar Surface Area (TPSA): 262.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.07
• H-Bond Acceptor: 18
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

• Deslanoside A
• Purpureaglycoside A
• L9D69XZ4TF
• DTXSID201315399
• AKOS040753657
• (3beta,5beta)-3-[(O-beta-D-Glucopyranosyl-(1-->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
• D-ribo-Hexopyranoside, digitoxigenin-3 O-beta-D-glucopyranosyl-(1-->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-->4)-2,6-dideoxy-, beta-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8285	82.85%
Caco-2	-	0.8931	89.31%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8184	81.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9300	93.00%
OATP1B3 inhibitior	+	0.9329	93.29%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8780	87.80%
P-glycoprotein inhibitior	+	0.7405	74.05%
P-glycoprotein substrate	+	0.8284	82.84%
CYP3A4 substrate	+	0.6960	69.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9010	90.10%
CYP3A4 inhibition	-	0.9194	91.94%
CYP2C9 inhibition	-	0.9182	91.82%
CYP2C19 inhibition	-	0.9284	92.84%
CYP2D6 inhibition	-	0.9380	93.80%
CYP1A2 inhibition	-	0.9197	91.97%
CYP2C8 inhibition	-	0.7845	78.45%
CYP inhibitory promiscuity	-	0.9237	92.37%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5893	58.93%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9204	92.04%
Skin irritation	-	0.5142	51.42%
Skin corrosion	-	0.9440	94.40%
Ames mutagenesis	-	0.5524	55.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.8839	88.39%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.9231	92.31%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8825	88.25%
Acute Oral Toxicity (c)	I	0.8499	84.99%
Estrogen receptor binding	+	0.8905	89.05%
Androgen receptor binding	+	0.8499	84.99%
Thyroid receptor binding	-	0.5988	59.88%
Glucocorticoid receptor binding	+	0.7444	74.44%
Aromatase binding	+	0.7692	76.92%
PPAR gamma	+	0.8228	82.28%
Honey bee toxicity	-	0.6320	63.20%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9475	94.75%

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	98.97%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.75%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.17%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.58%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.43%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.04%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.51%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.75%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.09%	95.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.47%	96.21%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.24%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.97%	95.89%
CHEMBL2581	P07339	Cathepsin D	85.19%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.70%	82.69%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.20%	97.25%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.52%	94.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.72%	92.94%
CHEMBL5255	O00206	Toll-like receptor 4	82.66%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.48%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	81.50%	95.93%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.81%	96.00%

Plants that contains it

• Digitalis purpurea

Cross-Links

• PubChem: 13178063
• LOTUS: LTS0081039
• wikiData: Q104950489