CHEBI:132245 - (2R,3S)-glycosmisic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name (2R,3S)-glycosmisic acid
ChEBI ID CHEBI:132245
ChEBI ASCII Name (2R,3S)-glycosmisic acid
Definition A member of the class of 1-benzofurans that is a lignan obtained by cyclodimerisation of ferulic acid. It is isolated from several plants including spearmint.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB22657057, ChemicalBook:CB12566507, eMolecules:26937692, ZINC000013514412
Download Molfile XML SDF
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+/m1/s1
InChIKey FHYQIQMSODIFCP-WARYXCEBSA-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
Tarenna attenuata (NCBI:txid1547788) See: Yang,J.Nat.Prod.,70,(2007),521
Mentha sp.cata (NCBI:txid29719) See: PubMed
Sphingobium sp. (NCBI:txid627192) of strain SYK-6 See: PubMed
Glycosmis citrifolia (NCBI:txid650008) See: Zhongguo yao xue za zhi (Zhongguo yao xue hui : 1989) 37, 14-17
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 )
bacterial xenobiotic metabolite
Any bacterial metabolite produced by metabolism of a xenobiotic compound in bacteria.
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 (2R,3S)-glycosmisic acid (CHEBI:132245) has functional parent trans-ferulic acid (CHEBI:17620)
(2R,3S)-glycosmisic acid (CHEBI:132245) has role bacterial xenobiotic metabolite (CHEBI:76976)
(2R,3S)-glycosmisic acid (CHEBI:132245) has role plant metabolite (CHEBI:76924)
(2R,3S)-glycosmisic acid (CHEBI:132245) is a glycosmisic acid (CHEBI:91209)
(2R,3S)-glycosmisic acid (CHEBI:132245) is conjugate acid of glycosmisate (CHEBI:131932)
(2R,3S)-glycosmisic acid (CHEBI:132245) is enantiomer of (2S,3R)-glycosmisic acid (CHEBI:132257)
Incoming glycosmisate (CHEBI:131932) is conjugate base of (2R,3S)-glycosmisic acid (CHEBI:132245)
(2S,3R)-glycosmisic acid (CHEBI:132257) is enantiomer of (2R,3S)-glycosmisic acid (CHEBI:132245)
IUPAC Name
(2E)-3-[(2R,3S)-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 ChEBI
spicatolignan B ChEBI
Manual Xrefs Databases
C00039281 KNApSAcK
CPD-17077 MetaCyc
View more database links
Registry Number Type Source
22023630 Reaxys Registry Number Reaxys
Citations Types Sources
17701560 PubMed citation Europe PMC
26362985 PubMed citation Europe PMC
368656 Chinese Abstracts citation Europe PMC
Last Modified
14 July 2016