Convallatoxin

Details

• Internal ID: a3289236-5c1b-46d2-9bc4-6e2e116e332b
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: (3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C4CCC5(C(CCC5(C4CCC3(C2)O)O)C6=CC(=O)OC6)C)C=O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CC[C@@]5([C@H](CC[C@@]5([C@@H]4CC[C@@]3(C2)O)O)C6=CC(=O)OC6)C)C=O)O)O)O
• InChI: InChI=1S/C29H42O10/c1-15-22(32)23(33)24(34)25(38-15)39-17-3-8-27(14-30)19-4-7-26(2)18(16-11-21(31)37-13-16)6-10-29(26,36)20(19)5-9-28(27,35)12-17/h11,14-15,17-20,22-25,32-36H,3-10,12-13H2,1-2H3/t15-,17-,18+,19-,20+,22-,23+,24+,25-,26+,27-,28-,29-/m0/s1
• InChI Key: HULMNSIAKWANQO-JQKSAQOKSA-N
• Popularity: 421 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₂O₁₀
• Molecular Weight: 550.60 g/mol
• Exact Mass: 550.27779753 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: -0.70

Synonyms

• 508-75-8
• Corglycone
• Convallotoxin
• Convallaton
• Korglykon
• Corglykon
• Convallatoxoside
• Convallaotoxin
• Corglycon
• Strophanthidin 3-O-alpha-L-rhamnoside
• CHEBI:27663
• Strophanthidin, 3-(6-deoxy-alpha-L-mannopyranoside)
• UNII-JY264VIR1Y
• JY264VIR1Y
• 3beta-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-5,14-dihydroxy-19-oxo-5beta-card-20(22)-enolide
• 3beta-(6-deoxy-alpha-L-mannopyranosyloxy)-5,14-dihydroxy-19-oxo-5beta-card-20(22)-enolide
• HSDB 3475
• Strophanthidin alpha-L-rhamnoside
• EINECS 208-086-3
• NSC 407808
• Rhamnoside, strophanthidin-3, alpha-L-
• Mannopyranoside, strophanthidin-3,6-deoxy-, alpha-L-
• Convallopan
• Convalpur
• Convapur
• NSC-407808
• C29-H42-O10
• Card-20(22)-enolide, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-5,14-dihydroxy-19-oxo-, (3beta,5beta)-
• Convallatoxin, >=65%
• CONVALLATOXIN [MI]
• D0M2QH
• SCHEMBL308440
• CONVALLATOXIN [WHO-DD]
• CHEMBL399336
• DTXSID90862073
• (3-beta,5-beta)-3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-5,14-dihydroxy-19-oxocard-20(22)-enolide
• (3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2,5-dihydrofuran-3-yl)-3-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)hexadecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• HY-N2453
• BDBM50480587
• LMST01120013
• AKOS040760350
• (3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• AC-35137
• MS-30077
• STROPHANTHIDIN .ALPHA.-L-RHAMNOSIDE
• CS-0022681
• C08858
• Q2996215
• 3beta-(alpha-L-rhamnopyranosyloxy)-5,14-dihydroxy-19-oxo-5beta-card-20(22)-enolide
• 5beta,14beta-Dihydroxy-19-oxo-3beta[(alpha-L-rhamnopyranosyl)oxy]card-20,22-enolide
• Card-20(22)-enolide, 3-[(6-deoxyhexopyranosyl)oxy]-5,14-dihydroxy-19-oxo-
• (3beta,5beta)-3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-5,14-dihydroxy-19-oxo-card-20(22)-enolide
• (3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• CARD-20(22)-ENOLIDE, 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-5,14-DIHYDROXY-19-OXO-, (3.BETA.,5.BETA.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4096	P04637	Cellular tumor antigen p53	39.8 nM	Potency	via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	223.9 nM; 281.8 nM; 223.9 nM	Potency; Potency; Potency	via Super-PRED; via Super-PRED; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.26%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.21%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.54%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.71%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.08%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.68%	97.36%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.84%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.43%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.12%	97.09%
CHEMBL4208	P20618	Proteasome component C5	87.97%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.26%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.16%	95.89%
CHEMBL3492	P49721	Proteasome Macropain subunit	86.24%	90.24%
CHEMBL2581	P07339	Cathepsin D	86.05%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.99%	92.94%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.78%	91.71%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.42%	96.77%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.94%	93.40%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.61%	85.14%
CHEMBL226	P30542	Adenosine A1 receptor	81.15%	95.93%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	80.11%	94.78%
CHEMBL1871	P10275	Androgen Receptor	80.04%	96.43%

Plants that contains it

• Adonis wolgensis
• Antiaris toxicaria
• Convallaria keiskei
• Convallaria majalis
• Crossosoma bigelovii
• Ornithogalum nutans
• Saussurea stella

Cross-Links

• PubChem: 441852
• NPASS: NPC251866
• ChEMBL: CHEMBL399336
• LOTUS: LTS0149239
• wikiData: Q2996215