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Showing metabocard for Maleic acid (HMDB0000176)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:55:53 UTC
HMDB IDHMDB0000176
Secondary Accession Numbers
  • HMDB00176
Metabolite Identification
Common NameMaleic acid
DescriptionMaleic acid is a dicarboxylic acid, a molecule with two carboxyl groups. It consists of an ethylene group flanked by two carboxylic acid groups. Maleic acid is the cis isomer of butenedioic acid, whereas fumaric acid is the trans isomer. The cis isomer is the less stable one of the two; the difference in heat of combustion is 22.7 kJ/mol. The physical properties of maleic acid are very different from that of fumaric acid. Maleic acid is soluble in water whereas fumaric acid is not and the melting point of maleic acid (130 - 131 oC) is also much lower than that of fumaric acid (287 oC). Maleic acid is converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation. Maleic acid is used in making polyesters for fibre-reinforced laminated moldings and paint vehicles. More specifically it is used in the manufacture of phthalic-type alkyd and polyester resins, surface coatings, copolymers, plasticizers, lubricant additives and agricultural chemicals. It is also found in adhesives and sealants and as a preservative for oils and fats. In the natural world, maleic acid has been identified in ginseng, pineapple, cacao plants, sour cherries and corn. A large number of microbes are able to convert maleic acid to D-malate using the enzyme maleate hydratase (PMID: 1444397 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000176 (Maleic acid)

  Mrv1652305271900202D          

  8  7  0  0  0  0            999 V2000
10000.3928 9999.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5678 9999.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8529 9999.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1382 9999.3865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.852910000.6234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.1083 9999.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8217 9999.3865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.108310000.6234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
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3D MOL for HMDB0000176 (Maleic acid)

HMDB0000176
     RDKit          3D
Maleic acid
 12 11  0  0  0  0  0  0  0  0999 V2000
    1.2932   -0.8164   -1.3800 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4817    0.0123   -0.4966 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8283    0.3986   -0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5510    0.6485    0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385    0.4793    0.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4643   -0.4198   -0.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9553   -1.1230   -1.2766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8802   -0.4971   -0.2006 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4399   -0.1199    0.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9409    1.3974    1.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2728    1.0808    1.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2240   -1.0407    0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  3  9  1  0
  4 10  1  0
  5 11  1  0
  8 12  1  0
M  END
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3D SDF for HMDB0000176 (Maleic acid)

  Mrv1652305271900202D          

  8  7  0  0  0  0            999 V2000
10000.3928 9999.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5678 9999.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8529 9999.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1382 9999.3865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.852910000.6234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.1083 9999.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8217 9999.3865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.108310000.6234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000176

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)\C=C/C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-

> <INCHI_KEY>
VZCYOOQTPOCHFL-UPHRSURJSA-N

> <FORMULA>
C4H4O4

> <MOLECULAR_WEIGHT>
116.0722

> <EXACT_MASS>
116.010958616

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
9.194281482540934

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-but-2-enedioic acid

> <ALOGPS_LOGP>
0.21

> <JCHEM_LOGP>
-0.040914331333333324

> <ALOGPS_LOGS>
-0.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.912485134930333

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.045732417201613

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
24.607

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.41e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
maleic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000176 (Maleic acid)

HMDB0000176
     RDKit          3D
Maleic acid
 12 11  0  0  0  0  0  0  0  0999 V2000
    1.2932   -0.8164   -1.3800 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4817    0.0123   -0.4966 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8283    0.3986   -0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5510    0.6485    0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385    0.4793    0.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4643   -0.4198   -0.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9553   -1.1230   -1.2766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8802   -0.4971   -0.2006 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4399   -0.1199    0.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9409    1.3974    1.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2728    1.0808    1.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2240   -1.0407    0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  3  9  1  0
  4 10  1  0
  5 11  1  0
  8 12  1  0
M  END
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PDB for HMDB0000176 (Maleic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    8667.4008665.521   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8665.8608665.521   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8664.5258666.290   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8663.1918665.521   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8664.5258667.830   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8668.7358666.290   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8670.0678665.521   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8668.7358667.830   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    1    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0000176 (Maleic acid)

COMPND    HMDB0000176
HETATM    1  O1  UNL     1       1.293  -0.816  -1.380  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.482   0.012  -0.497  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.828   0.399  -0.334  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.551   0.649   0.394  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.739   0.479   0.461  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.464  -0.420  -0.395  1.00  0.00           C  
HETATM    7  O3  UNL     1      -0.955  -1.123  -1.277  1.00  0.00           O  
HETATM    8  O4  UNL     1      -2.880  -0.497  -0.201  1.00  0.00           O  
HETATM    9  H1  UNL     1       3.440  -0.120   0.247  1.00  0.00           H  
HETATM   10  H2  UNL     1       0.941   1.397   1.149  1.00  0.00           H  
HETATM   11  H3  UNL     1      -1.273   1.081   1.235  1.00  0.00           H  
HETATM   12  H4  UNL     1      -3.224  -1.041   0.595  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    9
CONECT    4    5    5   10
CONECT    5    6   11
CONECT    6    7    7    8
CONECT    8   12
END
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SMILES for HMDB0000176 (Maleic acid)

OC(=O)\C=C/C(O)=O
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INCHI for HMDB0000176 (Maleic acid)

InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC4H4O4
Average Molecular Weight116.0722
Monoisotopic Molecular Weight116.010958616
IUPAC Name(2Z)-but-2-enedioic acid
Traditional Namemaleic acid
CAS Registry Number110-16-7
SMILES
OC(=O)\C=C/C(O)=O
InChI Identifier
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-
InChI KeyVZCYOOQTPOCHFL-UPHRSURJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point130.5 °CNot Available
Boiling Point355.00 to 356.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility441 mg/mL at 25 °CNot Available
LogP-0.48SANGSTER (1994)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available113.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00002070
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Fibroblasts
  • Neuron
  • Pancreas
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified1.585 +/- 1.123 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
Associated Disorders and Diseases
Disease References
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDDB04299
Phenol Explorer Compound IDNot Available
FooDB IDFDB008113
KNApSAcK IDC00007417
Chemspider ID392248
KEGG Compound IDC01384
BioCyc IDMALEATE
BiGG IDNot Available
Wikipedia LinkMaleic_acid
METLIN IDNot Available
PubChem Compound444266
PDB IDNot Available
ChEBI ID18300
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000084
Good Scents IDrw1256251
References
Synthesis ReferenceDethloff, Christian; Barbarino, Sergio. Process temperature optimization in the manufacture of maleic acid by the hydrolysis of maleic anhydride. Eur. Pat. Appl. (1998), 7 pp.
Material Safety Data Sheet (MSDS)Not Available
General References