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Showing metabocard for Mesaconic acid (HMDB0000749)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-09-22 18:34:14 UTC
HMDB IDHMDB0000749
Secondary Accession Numbers
  • HMDB00749
Metabolite Identification
Common NameMesaconic acid
DescriptionMesaconic acid, also known as 2-methylfumarate or citronic acid, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Mesaconic acid is a dicarboxylic butenoic acid, with a methyl group in position 2 and the double bound between carbons 2 and 3. Mesaconic acid was first studied for its physical properties in 1874 by Jacobus van ‘t Hoff (https://web.archive.org/web/20051117102410/http://dbhs.wvusd.k12.ca.us/webdocs/Chem-History/Van%27t-Hoff-1874.html). It is now known to be involved in the biosynthesis of vitamin B12 and it is also a competitor inhibitor of the reduction of fumarate.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000749 (Mesaconic acid)

  Mrv1652305271900202D          

  9  8  0  0  0  0            999 V2000
   -2.0087    0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232   -0.1339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0087    1.1035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942   -0.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942   -0.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5798    0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1346   -0.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1346   -0.9589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8491    0.2785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
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3D MOL for HMDB0000749 (Mesaconic acid)

HMDB0000749
     RDKit          3D
Mesaconic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -0.0546    1.1373    0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5199    0.0960   -0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -0.6398   -0.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898   -0.4114   -0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6457   -1.1216   -1.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3062    0.5342    0.3501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -0.1657   -0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659    0.5381    0.3320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4157   -1.1344   -1.1488 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834    1.9793    0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9778    1.6453    1.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4733    0.7713    1.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0616   -1.4257   -1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8003    0.3349    1.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2692   -2.1377   -1.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  2  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  6 14  1  0
  9 15  1  0
M  END
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3D SDF for HMDB0000749 (Mesaconic acid)

  Mrv1652305271900202D          

  9  8  0  0  0  0            999 V2000
   -2.0087    0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232   -0.1339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0087    1.1035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942   -0.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942   -0.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5798    0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1346   -0.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1346   -0.9589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8491    0.2785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000749

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+

> <INCHI_KEY>
HNEGQIOMVPPMNR-NSCUHMNNSA-N

> <FORMULA>
C5H6O4

> <MOLECULAR_WEIGHT>
130.0987

> <EXACT_MASS>
130.02660868

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.241128315164042

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-2-methylbut-2-enedioic acid

> <ALOGPS_LOGP>
0.21

> <JCHEM_LOGP>
0.35463615800000003

> <ALOGPS_LOGS>
-0.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.568292663140774

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.722300394674801

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
28.964100000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mesaconic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000749 (Mesaconic acid)

HMDB0000749
     RDKit          3D
Mesaconic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -0.0546    1.1373    0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5199    0.0960   -0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -0.6398   -0.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898   -0.4114   -0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6457   -1.1216   -1.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3062    0.5342    0.3501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -0.1657   -0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659    0.5381    0.3320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4157   -1.1344   -1.1488 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834    1.9793    0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9778    1.6453    1.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4733    0.7713    1.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0616   -1.4257   -1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8003    0.3349    1.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2692   -2.1377   -1.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  2  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  6 14  1  0
  9 15  1  0
M  END
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PDB for HMDB0000749 (Mesaconic 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      -3.750   0.520   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.083  -0.250   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -3.750   2.060   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.416  -0.250   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.416  -1.790   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.082   0.520   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.251  -0.250   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.251  -1.790   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.585   0.520   0.000  0.00  0.00           O+0
CONECT    1    4    3    2                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0000749 (Mesaconic acid)

COMPND    HMDB0000749
HETATM    1  C1  UNL     1      -0.055   1.137   0.875  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.520   0.096  -0.050  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.379  -0.640  -0.699  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.790  -0.411  -0.490  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.646  -1.122  -1.116  1.00  0.00           O  
HETATM    6  O2  UNL     1       2.306   0.534   0.350  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.936  -0.166  -0.288  1.00  0.00           C  
HETATM    8  O3  UNL     1      -2.766   0.538   0.332  1.00  0.00           O  
HETATM    9  O4  UNL     1      -2.416  -1.134  -1.149  1.00  0.00           O  
HETATM   10  H1  UNL     1       0.483   1.979   0.368  1.00  0.00           H  
HETATM   11  H2  UNL     1      -0.978   1.645   1.289  1.00  0.00           H  
HETATM   12  H3  UNL     1       0.473   0.771   1.762  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.062  -1.426  -1.397  1.00  0.00           H  
HETATM   14  H5  UNL     1       2.800   0.335   1.222  1.00  0.00           H  
HETATM   15  H6  UNL     1      -2.269  -2.138  -1.009  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    3    7
CONECT    3    4   13
CONECT    4    5    5    6
CONECT    6   14
CONECT    7    8    8    9
CONECT    9   15
END
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SMILES for HMDB0000749 (Mesaconic acid)

C\C(=C/C(O)=O)C(O)=O
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INCHI for HMDB0000749 (Mesaconic acid)

InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC5H6O4
Average Molecular Weight130.0987
Monoisotopic Molecular Weight130.02660868
IUPAC Name(2E)-2-methylbut-2-enedioic acid
Traditional Namemesaconic acid
CAS Registry Number498-24-8
SMILES
C\C(=C/C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+
InChI KeyHNEGQIOMVPPMNR-NSCUHMNNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • 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
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point200 - 202 °CNot Available
Boiling Point336.60 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility26.3 mg/mL at 18 °CNot Available
LogP0.540 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022221
KNApSAcK IDC00051539
Chemspider ID10289044
KEGG Compound IDC01732
BioCyc IDNot Available
BiGG ID38272
Wikipedia LinkMesaconic_acid
METLIN ID4130
PubChem Compound638129
PDB IDMEZ
ChEBI ID16600
Food Biomarker OntologyNot Available
VMH IDMESCON
MarkerDB IDNot Available
Good Scents IDrw1257141
References
Synthesis ReferenceShriner, R. L.; Ford, S. G.; Roll, L. J. Mesaconic acid. Organic Syntheses (1931), XI 74-5.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Truscott RJ, Malegan D, McCairns E, Burke D, Hick L, Sims P, Halpern B, Tanaka K, Sweetman L, Nyhan WL, Hammond J, Bumack C, Haan EA, Danks DM: New metabolites in isovaleric acidemia. Clin Chim Acta. 1981 Mar 5;110(2-3):187-203. [PubMed:6452974 ]