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CHEBI:15771 - loganin

Default Structure
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 3.2.1.20 (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.
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 3.1.1.7 (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.
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