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CHEBI:15771 - loganin

ChEBI IDCHEBI:15771
ChEBI Nameloganin
Stars
DefinitionAn iridoid monoterpenoid with formula C17H26O10 that is isolated from several plant species and exhibits neuroprotective and anti-inflammatory properties.
Secondary ChEBI IDsCHEBI:6513, CHEBI:14525, CHEBI:25069, CHEBI:132709
Last Modified4 July 2023
Submitterliuqingping
DownloadsMolfile
FormulaC17H26O10
Net Charge0
Average Mass390.385
Monoisotopic Mass390.15260
SMILES[H][C@]12[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)OC=C(C(=O)OC)[C@@]1([H])C[C@H](O)[C@@H]2C
InChIInChI=1S/C17H26O10/c1-6-9(19)3-7-8(15(23)24-2)5-25-16(11(6)7)27-17-14(22)13(21)12(20)10(4-18)26-17/h5-7,9-14,16-22H,3-4H2,1-2H3/t6-,7+,9-,10+,11+,12+,13-,14+,16-,17-/m0/s1
InChIKeyAMBQHHVBBHTQBF-UOUCRYGSSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Strychnos nux-blanda (ncbitaxon:1037791) root (BTO:0001188) PubMed (27534097)
Strychnos nux-vomica (ncbitaxon:28545) - PubMed (19666019)
Uncaria cordata (ncbitaxon:1382054) - PubMed (27128898)
Roles Classification
Biological Roles:
EC 3.1.1.7 (acetylcholinesterase) inhibitor  An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.
EC 3.4.23.46 (memapsin 2) inhibitor  An EC 3.4.23.* (aspartic endopeptidase) inhibitor that interferes with the activity of memapsin 2 (EC 3.4.23.46).
EC 3.2.1.20 (alpha-glucosidase) inhibitor  An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of α-glucosidase (EC 3.2.1.20).
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
ChEBI Ontology
Outgoing Relation(s)
loganin (CHEBI:15771) has functional parent loganetin (CHEBI:195298)
loganin (CHEBI:15771) has role anti-inflammatory agent (CHEBI:67079)
loganin (CHEBI:15771) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462)
loganin (CHEBI:15771) has role EC 3.2.1.20 (α-glucosidase) inhibitor (CHEBI:67239)
loganin (CHEBI:15771) has role EC 3.4.23.46 (memapsin 2) inhibitor (CHEBI:74925)
loganin (CHEBI:15771) has role neuroprotective agent (CHEBI:63726)
loganin (CHEBI:15771) has role plant metabolite (CHEBI:76924)
loganin (CHEBI:15771) is a cyclopentapyran (CHEBI:38606)
loganin (CHEBI:15771) is a enoate ester (CHEBI:51702)
loganin (CHEBI:15771) is a iridoid monoterpenoid (CHEBI:50563)
loganin (CHEBI:15771) is a methyl ester (CHEBI:25248)
loganin (CHEBI:15771) is a monosaccharide derivative (CHEBI:63367)
loganin (CHEBI:15771) is a secondary alcohol (CHEBI:35681)
loganin (CHEBI:15771) is a β-D-glucoside (CHEBI:22798)
Incoming Relation(s)
7-deoxyloganin (CHEBI:18370) has functional parent loganin (CHEBI:15771)
IUPAC Name 
methyl (1S,4aS,6S,7R,7aS)-1-(β-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Synonyms  Source
1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylic acid methyl esterChEBI
LoganinKEGG COMPOUND
loganosideChEBI
UniProt Name  Source
loganinUniProt
Manual XrefsDatabases
91727262PubChem Compound
C00003088KNApSAcK
C01433KEGG COMPOUND
C01433KEGG COMPOUND
LMPR0102070001LIPID MAPS
LoganinWikipedia
LOGANINMetaCyc
Registry NumbersSources
Reaxys:55724Reaxys
CAS:18524-94-2ChemIDplus
CAS:18524-94-2KEGG COMPOUND
Citations