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ChEBI
> Main
CHEBI:132257 - (2
S
,3
R
)-glycosmisic acid
Main
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ChEBI Name
(2
S
,3
R
)-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.
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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 (Br
o
nsted 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
(2
S
,3
R
)-glycosmisic acid (
CHEBI:132257
)
has functional parent
ferulic acid (
CHEBI:17620
)
(2
S
,3
R
)-glycosmisic acid (
CHEBI:132257
)
has role
plant metabolite (
CHEBI:76924
)
(2
S
,3
R
)-glycosmisic acid (
CHEBI:132257
)
is a
α,β-unsaturated monocarboxylic acid (
CHEBI:79020
)
(2
S
,3
R
)-glycosmisic acid (
CHEBI:132257
)
is a
glycosmisic acid (
CHEBI:91209
)
(2
S
,3
R
)-glycosmisic acid (
CHEBI:132257
)
is conjugate acid of
ent
-glycosmisate (
CHEBI:131937
)
(2
S
,3
R
)-glycosmisic acid (
CHEBI:132257
)
is enantiomer of
(2
R
,3
S
)-glycosmisic acid (
CHEBI:132245
)
Incoming
ent
-glycosmisate (
CHEBI:131937
)
is conjugate base of
(2
S
,3
R
)-glycosmisic acid (
CHEBI:132257
)
(2
R
,3
S
)-glycosmisic acid (
CHEBI:132245
)
is enantiomer of
(2
S
,3
R
)-glycosmisic acid (
CHEBI:132257
)
IUPAC Name
(2
E
)-
3-
[(2
S
,3
R
)-
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
Type
Source
26362985
PubMed citation
Europe PMC
Last Modified
14 July 2016