CHEBI:15771 - loganin

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ChEBI Name loganin
ChEBI ID CHEBI:15771
Definition An iridoid monoterpenoid with formula C17H26O10 that is isolated from several plant species and exhibits neuroprotective and anti-inflammatory properties.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter qingping liu
Secondary ChEBI IDs CHEBI:132709, CHEBI:6513, CHEBI:14525, CHEBI:25069
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Formula C17H26O10
Net Charge 0
Average Mass 390.38234
Monoisotopic Mass 390.153
InChI InChI=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
InChIKey AMBQHHVBBHTQBF-UOUCRYGSSA-N
SMILES [H][C@]12C[C@H](O)[C@H](C)[C@@]1([H])[C@@H](OC=C2C(=O)OC)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Metabolite of Species Details
Strychnos nux-blanda (NCBI:txid1037791) Found in root (BTO:0001188). See: PubMed
Uncaria cordata (NCBI:txid1382054) See: PubMed
Strychnos nux-vomica (NCBI:txid28545) See: PubMed
Roles Classification
Biological Role(s): 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 3.2.1.20 (alpha-glucosidase) inhibitor
An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-glucosidase (EC 3.2.1.20).
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.
Application(s): neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 β-D-glucoside (CHEBI:22798)
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)
Incoming 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 Sources
1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylic acid methyl ester ChEBI
Loganin KEGG COMPOUND
loganin UniProt
loganoside ChEBI
Manual Xrefs Databases
91727262 PubChem
C00003088 KNApSAcK
C01433 KEGG COMPOUND
LMPR0102070001 LIPID MAPS
Loganin Wikipedia
LOGANIN MetaCyc
View more database links
Registry Numbers Types Sources
18524-94-2 CAS Registry Number KEGG COMPOUND
18524-94-2 CAS Registry Number ChemIDplus
55724 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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IND500719365 Agricola citation Europe PMC
Last Modified
11 January 2017