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ChEBI
> Main
CHEBI:132245 - (2
R
,3
S
)-glycosmisic acid
Main
ChEBI Ontology
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ChEBI Name
(2
R
,3
S
)-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.
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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+/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 (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
)
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
(2
R
,3
S
)-glycosmisic acid (
CHEBI:132245
)
has functional parent
ferulic acid (
CHEBI:17620
)
(2
R
,3
S
)-glycosmisic acid (
CHEBI:132245
)
has role
bacterial xenobiotic metabolite (
CHEBI:76976
)
(2
R
,3
S
)-glycosmisic acid (
CHEBI:132245
)
has role
plant metabolite (
CHEBI:76924
)
(2
R
,3
S
)-glycosmisic acid (
CHEBI:132245
)
is a
glycosmisic acid (
CHEBI:91209
)
(2
R
,3
S
)-glycosmisic acid (
CHEBI:132245
)
is conjugate acid of
glycosmisate (
CHEBI:131932
)
(2
R
,3
S
)-glycosmisic acid (
CHEBI:132245
)
is enantiomer of
(2
S
,3
R
)-glycosmisic acid (
CHEBI:132257
)
Incoming
glycosmisate (
CHEBI:131932
)
is conjugate base of
(2
R
,3
S
)-glycosmisic acid (
CHEBI:132245
)
(2
S
,3
R
)-glycosmisic acid (
CHEBI:132257
)
is enantiomer of
(2
R
,3
S
)-glycosmisic acid (
CHEBI:132245
)
IUPAC Name
(2
E
)-
3-
[(2
R
,3
S
)-
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