EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:149585 - ligstroside

ChEBI IDCHEBI:149585
ChEBI Nameligstroside
Stars
DefinitionA secoiridoid glycoside that is the methyl ester of 3,4-dihydro-2H-pyran-5-carboxylic acid which is substituted at positions 2, 3, and 4 by hydroxy, ethylidene, and carboxymethyl groups, respectively and in which the anomeric hydroxy group at position 2 has been converted into its β-D-glucoside and the carboxylic acid moiety of the carboxymethyl substituent has been converted to the corresponding 4-hydroxyphenethyl ester (the 2S,3E,4S stereoisomer). An important phenolic compound present in olive cultivars.
Last Modified27 May 2020
Submittermwilliams
DownloadsMolfile
FormulaC25H32O12
Net Charge0
Average Mass524.519
Monoisotopic Mass524.18938
SMILES[H][C@@]1(CC(=O)OCCc2ccc(O)cc2)C(C(=O)OC)=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)/C1=C/C
InChIInChI=1S/C25H32O12/c1-3-15-16(10-19(28)34-9-8-13-4-6-14(27)7-5-13)17(23(32)33-2)12-35-24(15)37-25-22(31)21(30)20(29)18(11-26)36-25/h3-7,12,16,18,20-22,24-27,29-31H,8-11H2,1-2H3/b15-3+/t16-,18+,20+,21-,22+,24-,25-/m0/s1
InChIKeyGMQXOLRKJQWPNB-MVVLSVRYSA-N
Species of MetaboliteComponentSourceComments
Fraxinus angustifolia (ncbitaxon:166594) leaf (BTO:0000713) PubMed (32298276)
Olea europaea (ncbitaxon:4146) - PubMed (31578603)
Roles Classification
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
ligstroside (CHEBI:149585) has role antineoplastic agent (CHEBI:35610)
ligstroside (CHEBI:149585) has role plant metabolite (CHEBI:76924)
ligstroside (CHEBI:149585) is a diester (CHEBI:51307)
ligstroside (CHEBI:149585) is a methyl ester (CHEBI:25248)
ligstroside (CHEBI:149585) is a phenols (CHEBI:33853)
ligstroside (CHEBI:149585) is a pyrans (CHEBI:26407)
ligstroside (CHEBI:149585) is a secoiridoid glycoside (CHEBI:50274)
ligstroside (CHEBI:149585) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
methyl (2S,3E,4S)-3-ethylidene-2-(β-D-glucopyranosyloxy)-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-3,4-dihydro-2H-pyran-5-carboxylate
Synonyms  Source
ligusrosideChemIDplus
(−)-ligstrosideKNApSAcK
Manual XrefsDatabases
FDB013297FooDB
C00010785KNApSAcK
CPD-20220MetaCyc
HMDB0034751HMDB
Registry NumbersSources
CAS:35897-92-8ChemIDplus
Citations