CHEBI:7522 - neriifolin

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ChEBI Name neriifolin
ChEBI ID CHEBI:7522
Definition A cardenolide glycoside that is digitoxigenin in which the hydroxy goup at position 3 has been converted to its (6-deoxy-3-O-methyl-α-L-glucopyranoside derivative. Found in the seeds of Cerbera odollamand in Thevetia ahouia and Thevitia neriifolia.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C30H46O8
Net Charge 0
Average Mass 534.68144
Monoisotopic Mass 534.319
InChI InChI=1S/C30H46O8/c1-16-24(32)26(35-4)25(33)27(37-16)38-19-7-10-28(2)18(14-19)5-6-22-21(28)8-11-29(3)20(9-12-30(22,29)34)17-13-23(31)36-15-17/h13,16,18-22,24-27,32-34H,5-12,14-15H2,1-4H3/t16-,18+,19-,20+,21-,22+,24-,25-,26+,27-,28-,29+,30-/m0/s1
InChIKey VPUNMTHWNSJUOG-BAOINKAISA-N
SMILES [H][C@]12CC[C@]3([H])[C@]([H])(CC[C@]4(C)[C@]([H])(CC[C@]34O)C3=CC(=O)OC3)[C@@]1(C)CC[C@@H](C2)O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](OC)[C@@H]1O
Roles Classification
Biological Role(s): toxin
Poisonous substance produced by a biological organism such as a microbe, animal or plant.
Application(s): neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
cardiotonic drug
A drug that has a strengthening effect on the heart or that can increase cardiac output.
cardioprotective agent
Any protective agent that is able to prevent damage to the heart.
(via cardiac glycoside )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing neriifolin (CHEBI:7522) has functional parent digitoxigenin (CHEBI:42219)
neriifolin (CHEBI:7522) has role cardiotonic drug (CHEBI:38147)
neriifolin (CHEBI:7522) has role neuroprotective agent (CHEBI:63726)
neriifolin (CHEBI:7522) has role toxin (CHEBI:27026)
neriifolin (CHEBI:7522) is a cardenolide glycoside (CHEBI:38092)
Incoming cerberin (CHEBI:75049) has functional parent neriifolin (CHEBI:7522)
IUPAC Name
3β-(6-deoxy-3-O-methyl-α-L-glucopyranosyloxy)-14-hydroxy-5β-card-20(22)-enolide
Synonyms Sources
Digitoxigenin 3-(alpha-L-thevetoside) KEGG COMPOUND
Neriifolin KEGG COMPOUND
Database Links Databases
C00003632 KNApSAcK
C08876 KEGG COMPOUND
LMST01120021 LIPID MAPS
View more database links
Registry Numbers Types Sources
100752 Beilstein Registry Number Beilstein
466-07-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
14783447 PubMed citation Europe PMC
14790880 PubMed citation Europe PMC
16793926 PubMed citation Europe PMC
19306191 PubMed citation Europe PMC
19591858 PubMed citation Europe PMC
20438743 PubMed citation Europe PMC
21459134 PubMed citation Europe PMC
22563390 PubMed citation Europe PMC
6677038 PubMed citation Europe PMC
IND22067651 Agricola citation Europe PMC
Last Modified
28 July 2014