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ChEBI
> Main
CHEBI:18300 - maleic acid
Main
ChEBI Ontology
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ChEBI Name
maleic acid
ChEBI ID
CHEBI:18300
Definition
A butenedioic acid in which the double bond has
cis
- (
Z
)-configuration.
Stars
This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs
CHEBI:43836, CHEBI:6653, CHEBI:25119
Supplier Information
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Wikipedia
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Read full article at Wikipedia
Formula
C4H4O4
Net Charge
0
Average Mass
116.07216
Monoisotopic Mass
116.01096
InChI
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-
InChIKey
VZCYOOQTPOCHFL-UPHRSURJSA-N
SMILES
OC(=O)\C=C/C(O)=O
Metabolite of Species
Details
Mus musculus
(NCBI:txid10090)
Source: BioModels - MODEL1507180067 See:
PubMed
Chlamydomonas reinhardtii
(NCBI:txid3055)
See:
PubMed
Arabidopsis thaliana
(NCBI:txid3702)
Found in leaf
(BTO:0000713)
. 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.
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (
Mus musculus
).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
maleic acid (
CHEBI:18300
)
has role
algal metabolite (
CHEBI:84735
)
maleic acid (
CHEBI:18300
)
has role
mouse metabolite (
CHEBI:75771
)
maleic acid (
CHEBI:18300
)
has role
plant metabolite (
CHEBI:76924
)
maleic acid (
CHEBI:18300
)
is a
butenedioic acid (
CHEBI:22958
)
maleic acid (
CHEBI:18300
)
is conjugate acid of
maleate (
CHEBI:132951
)
maleic acid (
CHEBI:18300
)
is conjugate acid of
maleate(1−) (
CHEBI:37156
)
Incoming
2-(ω-methylthio)alkylmaleic acid (
CHEBI:134534
)
has functional parent
maleic acid (
CHEBI:18300
)
2-isopropylmaleic acid (
CHEBI:17275
)
has functional parent
maleic acid (
CHEBI:18300
)
N
-formylmaleamic acid (
CHEBI:59930
)
has functional parent
maleic acid (
CHEBI:18300
)
citraconic acid (
CHEBI:17626
)
has functional parent
maleic acid (
CHEBI:18300
)
dimethylmaleic acid (
CHEBI:23812
)
has functional parent
maleic acid (
CHEBI:18300
)
maleamic acid (
CHEBI:29045
)
has functional parent
maleic acid (
CHEBI:18300
)
maleate ester (
CHEBI:35486
)
has functional parent
maleic acid (
CHEBI:18300
)
maleimide (
CHEBI:16072
)
has functional parent
maleic acid (
CHEBI:18300
)
maleimides (
CHEBI:55417
)
has functional parent
maleic acid (
CHEBI:18300
)
maleate (
CHEBI:132951
)
is conjugate base of
maleic acid (
CHEBI:18300
)
maleate(1−) (
CHEBI:37156
)
is conjugate base of
maleic acid (
CHEBI:18300
)
(
Z
)-3-carboxyprop-2-enoyl group (
CHEBI:25122
)
is substituent group from
maleic acid (
CHEBI:18300
)
maleoyl group (
CHEBI:25121
)
is substituent group from
maleic acid (
CHEBI:18300
)
IUPAC Name
(2
Z
)-but-2-enedioic acid
Synonyms
Sources
(
Z
)-2-butenedioic acid
NIST Chemistry WebBook
(
Z
)-butenedioic acid
NIST Chemistry WebBook
cis
-1,2-ethylenedicarboxylic acid
NIST Chemistry WebBook
cis
-but-2-enedioic acid
IUPAC
cis-Butenedioic acid
KEGG COMPOUND
cis
-ethene-1,2-dioic acid
ChEBI
H
2
male
IUPAC
Maleic acid
KEGG COMPOUND
MALEIC ACID
PDBeChem
toxilic acid
NIST Chemistry WebBook
Manual Xrefs
Databases
C00007417
KNApSAcK
C01384
KEGG COMPOUND
DB04299
DrugBank
HMDB0000176
HMDB
MAE
PDBeChem
MALEATE
MetaCyc
Maleic_acid
Wikipedia
View more database links
Registry Numbers
Types
Sources
110-16-7
CAS Registry Number
KEGG COMPOUND
110-16-7
CAS Registry Number
ChemIDplus
110-16-7
CAS Registry Number
NIST Chemistry WebBook
1903639
Beilstein Registry Number
Beilstein
49854
Gmelin Registry Number
Gmelin
605762
Beilstein Registry Number
Beilstein
605762
Reaxys Registry Number
Reaxys
Citations
Types
Sources
10952545
PubMed citation
Europe PMC
11386868
PubMed citation
Europe PMC
22770225
PubMed citation
Europe PMC
9591280
PubMed citation
Europe PMC
Last Modified
18 October 2023