CHEBI:149585 - ligstroside

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ChEBI Name ligstroside
ChEBI ID CHEBI:149585
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Mark Williams
Supplier Information
Download Molfile XML SDF
Formula C25H32O12
Net Charge 0
Average Mass 524.519
Monoisotopic Mass 524.18938
InChI InChI=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
InChIKey GMQXOLRKJQWPNB-MVVLSVRYSA-N
SMILES [C@@H]1([C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O[C@H]2/C(/[C@](C(=CO2)C(=O)OC)([H])CC(=O)OCCC=3C=CC(=CC3)O)=C/C
Metabolite of Species Details
Fraxinus angustifolia (NCBI:txid166594) Found in leaf (BTO:0000713). See: PubMed
Olea europaea (NCBI:txid4146) 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.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ligstroside (CHEBI:149585) has role antineoplastic agent (CHEBI:35610)
ligstroside (CHEBI:149585) has role plant metabolite (CHEBI:76924)
ligstroside (CHEBI:149585) is a β-D-glucoside (CHEBI:22798)
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)
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 Sources
(−)-ligstroside KNApSAcK
ligusroside ChemIDplus
Manual Xrefs Databases
C00010785 KNApSAcK
CPD-20220 MetaCyc
FDB013297 FooDB
HMDB0034751 HMDB
View more database links
Registry Number Type Source
35897-92-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11561446 PubMed citation Europe PMC
19689134 PubMed citation Europe PMC
29163620 PubMed citation Europe PMC
29424233 PubMed citation Europe PMC
30381176 PubMed citation Europe PMC
31578603 PubMed citation Europe PMC
32084452 PubMed citation Europe PMC
32298276 PubMed citation Europe PMC
Last Modified
27 May 2020