CHEBI:132257 - (2S,3R)-glycosmisic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name (2S,3R)-glycosmisic acid
ChEBI ID CHEBI:132257
ChEBI ASCII Name (2S,3R)-glycosmisic acid
Definition A member of the class of 1-benzofurans that is a lignan obtained by cyclodimerisation of ferulic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H20O7
Net Charge 0
Average Mass 372.369
Monoisotopic Mass 372.12090
InChI InChI=1S/C20H20O7/c1-25-16-9-12(4-5-15(16)22)19-14(10-21)13-7-11(3-6-18(23)24)8-17(26-2)20(13)27-19/h3-9,14,19,21-22H,10H2,1-2H3,(H,23,24)/b6-3+/t14-,19+/m0/s1
InChIKey FHYQIQMSODIFCP-ZMOFONSMSA-N
SMILES C1=C(C=C2C(=C1OC)O[C@@H]([C@H]2CO)C3=CC=C(C(=C3)OC)O)/C=C/C(O)=O
Metabolite of Species Details
Sphingobium sp. (NCBI:txid627192) of strain SYK-6 See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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.
(via glycosmisic acid )
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
(via guaiacyl lignin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (2S,3R)-glycosmisic acid (CHEBI:132257) has functional parent ferulic acid (CHEBI:17620)
(2S,3R)-glycosmisic acid (CHEBI:132257) has role plant metabolite (CHEBI:76924)
(2S,3R)-glycosmisic acid (CHEBI:132257) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
(2S,3R)-glycosmisic acid (CHEBI:132257) is a glycosmisic acid (CHEBI:91209)
(2S,3R)-glycosmisic acid (CHEBI:132257) is conjugate acid of ent-glycosmisate (CHEBI:131937)
(2S,3R)-glycosmisic acid (CHEBI:132257) is enantiomer of (2R,3S)-glycosmisic acid (CHEBI:132245)
Incoming ent-glycosmisate (CHEBI:131937) is conjugate base of (2S,3R)-glycosmisic acid (CHEBI:132257)
(2R,3S)-glycosmisic acid (CHEBI:132245) is enantiomer of (2S,3R)-glycosmisic acid (CHEBI:132257)
IUPAC Name
(2E)-3-[(2S,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoic acid
Synonyms Sources
(+)-DCA C MetaCyc
(+)-dehydrodiconiferyl acid MetaCyc
ent-glycosmisic acid ChEBI
ent-spicatolignan B ChEBI
Manual Xref Database
CPD-18963 MetaCyc
View more database links
Registry Number Type Source
7663833 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
26362985 PubMed citation Europe PMC
Last Modified
14 July 2016