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
Supplier Information eMolecules:36095329, eMolecules:31240093, eMolecules:28169021, ZINC000003978792
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Formula C17H26O10
Net Charge 0
Average Mass 390.38234
Monoisotopic Mass 390.15260
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 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 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
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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
19666019 PubMed citation Europe PMC
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IND500719365 Agricola citation Europe PMC
Last Modified
04 July 2023