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Showing metabocard for Mesoxalic acid (HMDB0031522)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:43:49 UTC
Update Date2023-02-21 17:20:44 UTC
HMDB IDHMDB0031522
Secondary Accession Numbers
  • HMDB31522
Metabolite Identification
Common NameMesoxalic acid
DescriptionMesoxalic acid, also known as ketomalonic acid or a-ketomalonate, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Mesoxalic acid has been detected, but not quantified in, several different foods, such as breakfast cereal, cereals and cereal products, common peas (Pisum sativum), and herbs and spices. This could make mesoxalic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Mesoxalic acid.
Structure
Data?1677000044
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031522 (Mesoxalic acid)


  Mrv0541 02231217022D          

  8  7  0  0  0  0            999 V2000
    1.2375    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  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 HMDB0031522 (Mesoxalic acid)

HMDB0031522
     RDKit          3D
Mesoxalic acid
 10  9  0  0  0  0  0  0  0  0999 V2000
    1.2077   -1.4824   -0.4554 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1523   -0.2196   -0.4367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3314    0.4503   -0.7383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0675    0.4563   -0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950    1.7159   -0.1085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2700   -0.2966    0.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2214   -1.5509    0.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4673    0.3253    0.4981 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405    0.1244   -0.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8107    0.4773    1.4195 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
  4  6  1  0
  6  7  2  0
  6  8  1  0
  3  9  1  0
  8 10  1  0
M  END
Download

3D SDF for HMDB0031522 (Mesoxalic acid)


  Mrv0541 02231217022D          

  8  7  0  0  0  0            999 V2000
    1.2375    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031522

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C3H2O5/c4-1(2(5)6)3(7)8/h(H,5,6)(H,7,8)

> <INCHI_KEY>
XEEVLJKYYUVTRC-UHFFFAOYSA-N

> <FORMULA>
C3H2O5

> <MOLECULAR_WEIGHT>
118.045

> <EXACT_MASS>
117.990223174

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
8.0490078164927

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxopropanedioic acid

> <ALOGPS_LOGP>
-0.43

> <JCHEM_LOGP>
0.025468098333333355

> <ALOGPS_LOGS>
-0.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.72307514560714

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5608712626362866

> <JCHEM_POLAR_SURFACE_AREA>
91.66999999999999

> <JCHEM_REFRACTIVITY>
19.7846

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mesoxalic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0031522 (Mesoxalic acid)

HMDB0031522
     RDKit          3D
Mesoxalic acid
 10  9  0  0  0  0  0  0  0  0999 V2000
    1.2077   -1.4824   -0.4554 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1523   -0.2196   -0.4367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3314    0.4503   -0.7383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0675    0.4563   -0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950    1.7159   -0.1085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2700   -0.2966    0.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2214   -1.5509    0.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4673    0.3253    0.4981 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405    0.1244   -0.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8107    0.4773    1.4195 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
  4  6  1  0
  6  7  2  0
  6  8  1  0
  3  9  1  0
  8 10  1  0
M  END
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PDB for HMDB0031522 (Mesoxalic acid)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       2.310   4.001   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000   2.667   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    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 HMDB0031522 (Mesoxalic acid)

COMPND    HMDB0031522
HETATM    1  O1  UNL     1       1.208  -1.482  -0.455  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.152  -0.220  -0.437  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.331   0.450  -0.738  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.067   0.456  -0.120  1.00  0.00           C  
HETATM    5  O3  UNL     1      -0.095   1.716  -0.109  1.00  0.00           O  
HETATM    6  C3  UNL     1      -1.270  -0.297   0.187  1.00  0.00           C  
HETATM    7  O4  UNL     1      -1.221  -1.551   0.171  1.00  0.00           O  
HETATM    8  O5  UNL     1      -2.467   0.325   0.498  1.00  0.00           O  
HETATM    9  H1  UNL     1       3.241   0.124  -0.417  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.811   0.477   1.420  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    9
CONECT    4    5    5    6
CONECT    6    7    7    8
CONECT    8   10
END
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SMILES for HMDB0031522 (Mesoxalic acid)

OC(=O)C(=O)C(O)=O
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INCHI for HMDB0031522 (Mesoxalic acid)

InChI=1S/C3H2O5/c4-1(2(5)6)3(7)8/h(H,5,6)(H,7,8)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
ALPHA-KETOMALONIC ACIDChEBI
Ketomalonic acidChEBI
Oxomalonic acidKegg
a-KETOMALONateGenerator
a-KETOMALONic acidGenerator
alpha-KETOMALONateGenerator
Α-ketomalonateGenerator
Α-ketomalonic acidGenerator
KetomalonateGenerator
OxomalonateGenerator
MesoxalateGenerator
2-Oxomalonic acidHMDB
2-Oxopropanedioic acidHMDB
Mesoxalic acid, 8ciHMDB
Propanedioic acid, oxo- (9ci)HMDB
Mesoxalic acidChEBI
Chemical FormulaC3H2O5
Average Molecular Weight118.045
Monoisotopic Molecular Weight117.990223174
IUPAC Name2-oxopropanedioic acid
Traditional Namemesoxalic acid
CAS Registry Number473-90-5
SMILES
OC(=O)C(=O)C(O)=O
InChI Identifier
InChI=1S/C3H2O5/c4-1(2(5)6)3(7)8/h(H,5,6)(H,7,8)
InChI KeyXEEVLJKYYUVTRC-UHFFFAOYSA-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
  • Keto acid
  • Dicarboxylic acid or derivatives
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • 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 locationRoute of exposureSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility14.5 g/LALOGPS
logP-0.43ALOGPS
logP0.025ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)1.56ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.78 m³·mol⁻¹ChemAxon
Polarizability8.05 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+124.08331661259
DarkChem[M-H]-120.54531661259
DeepCCS[M+H]+122.39130932474
DeepCCS[M-H]-119.58930932474
DeepCCS[M-2H]-156.09330932474
DeepCCS[M+Na]+130.82830932474
AllCCS[M+H]+128.532859911
AllCCS[M+H-H2O]+124.332859911
AllCCS[M+NH4]+132.532859911
AllCCS[M+Na]+133.632859911
AllCCS[M-H]-118.132859911
AllCCS[M+Na-2H]-121.232859911
AllCCS[M+HCOO]-124.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Mesoxalic acidOC(=O)C(=O)C(O)=O1427.8Standard polar33892256
Mesoxalic acidOC(=O)C(=O)C(O)=O1595.1Standard non polar33892256
Mesoxalic acidOC(=O)C(=O)C(O)=O967.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Mesoxalic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)C(=O)O1155.6Semi standard non polar33892256
Mesoxalic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)C(=O)O[Si](C)(C)C1311.5Semi standard non polar33892256
Mesoxalic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)C(=O)O1417.1Semi standard non polar33892256
Mesoxalic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)C(=O)O[Si](C)(C)C(C)(C)C1753.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Mesoxalic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9200000000-7f3187d48fd7cdaaa7c42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mesoxalic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00dj-8910000000-61bed3d466b74650f63f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mesoxalic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Mesoxalic acid 20V, Negative-QTOFsplash10-074j-9000000000-913aeab7c908127f50d22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mesoxalic acid 10V, Negative-QTOFsplash10-00xr-9600000000-62124ac2f912829446072021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mesoxalic acid 40V, Negative-QTOFsplash10-004i-9000000000-3a8b99efe83ad97557642021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoxalic acid 10V, Positive-QTOFsplash10-014i-0900000000-c19217750b6232bee1432016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoxalic acid 20V, Positive-QTOFsplash10-014i-1900000000-1a80bc24684415bcd7932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoxalic acid 40V, Positive-QTOFsplash10-016r-9500000000-4b6aa572aec4dd8647f02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoxalic acid 10V, Negative-QTOFsplash10-01b9-6900000000-1a7307b6f229e9a805022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoxalic acid 20V, Negative-QTOFsplash10-01b9-8900000000-b9108b694f36f73160942016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoxalic acid 40V, Negative-QTOFsplash10-00di-9000000000-a364a9226599a44b9d252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoxalic acid 10V, Negative-QTOFsplash10-00di-9000000000-c6f38ec60bcf8724ecd12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoxalic acid 20V, Negative-QTOFsplash10-00di-9000000000-c6f38ec60bcf8724ecd12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoxalic acid 40V, Negative-QTOFsplash10-00di-9000000000-d3496f5f0ee9812df0ad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoxalic acid 10V, Positive-QTOFsplash10-0udi-9800000000-32883d33fe30e57cd56e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoxalic acid 20V, Positive-QTOFsplash10-052f-9000000000-943ce208216c1ca7e5fd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesoxalic acid 40V, Positive-QTOFsplash10-0006-9000000000-79ca31c8c933a6d983c62021-09-23Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03589
Phenol Explorer Compound IDNot Available
FooDB IDFDB008123
KNApSAcK IDC00057401
Chemspider ID9727
KEGG Compound IDC00830
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMesoxalic acid
METLIN IDNot Available
PubChem Compound10132
PDB IDMAK
ChEBI ID30842
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1499711
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details
1. NAD-dependent malic enzyme, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ME2
Uniprot ID:
P23368
Molecular weight:
53585.73
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]