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Showing metabocard for Glyoxylic acid (HMDB0000119)

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enzymes (9)transporters (1) Show 10 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-11-09 23:12:07 UTC
HMDB IDHMDB0000119
Secondary Accession Numbers
  • HMDB00119
Metabolite Identification
Common NameGlyoxylic acid
DescriptionGlyoxylic acid or oxoacetic acid is an organic compound that is both an aldehyde and a carboxylic acid. Glyoxylic acid is a liquid with a melting point of -93°C and a boiling point of 111°C. It is an intermediate of the glyoxylate cycle, which enables certain organisms to convert fatty acids into carbohydrates. The conjugate base of glyoxylic acid is known as glyoxylate (PMID: 16396466 ). In humans, glyoxylate is produced via two pathways: (1) through the oxidation of glycolate in peroxisomes and (2) through the catabolism of hydroxyproline in mitochondria. In the peroxisomes, glyoxylate is converted into glycine by glyoxylate aminotransferase (AGT1) or into oxalate by glycolate oxidase. In the mitochondria, glyoxylate is converted into glycine by mitochondrial glyoxylate aminotransferase AGT2 or into glycolate by glycolate reductase. A small amount of glyoxylate is converted into oxalate by cytoplasmic lactate dehydrogenase. Glyoxylic acid is found to be associated with primary hyperoxaluria I, which is an inborn error of metabolism. Under certain circumstances, glyoxylate can be a nephrotoxin and a metabotoxin. A nephrotoxin is a compound that causes damage to the kidney and kidney tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. High levels of glyoxylate are involved in the development of hyperoxaluria, a key cause of nephrolithiasis (commonly known as kidney stones). Glyoxylate is both a substrate and inductor of sulfate anion transporter-1 (SAT-1), a gene responsible for oxalate transportation, allowing it to increase SAT-1 mRNA expression, and as a result oxalate efflux from the cell. The increased oxalate release allows the buildup of calcium oxalate in the urine, and thus the eventual formation of kidney stones. As an aldehyde, glyoxylate is also highly reactive and will modify proteins to form advanced glycation products (AGEs).
Structure
Data?1582752112
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000119 (Glyoxylic acid)


  Mrv1652309032023522D          

  5  4  0  0  0  0            999 V2000
   -0.6695    0.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3841   -0.2901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6695    0.9474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0450   -0.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7595    0.1223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
  4  5  2  0  0  0  0
M  END
Download

3D MOL for HMDB0000119 (Glyoxylic acid)

HMDB0000119
     RDKit          3D
Glyoxylic acid
  7  6  0  0  0  0  0  0  0  0999 V2000
    1.4768   -0.7904   -0.6827 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0212    0.1407    0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4045    0.3577    0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8334    1.2923    0.8145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3383   -0.4315   -0.5449 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6984    0.7792    0.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6202   -1.3481   -0.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  5  7  1  0
M  END
Download

3D SDF for HMDB0000119 (Glyoxylic acid)


  Mrv1652309032023522D          

  5  4  0  0  0  0            999 V2000
   -0.6695    0.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3841   -0.2901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6695    0.9474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0450   -0.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7595    0.1223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
  4  5  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000119

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)

> <INCHI_KEY>
HHLFWLYXYJOTON-UHFFFAOYSA-N

> <FORMULA>
C2H2O3

> <MOLECULAR_WEIGHT>
74.0355

> <EXACT_MASS>
74.00039393

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
5.350371249097624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxoacetic acid

> <ALOGPS_LOGP>
-0.59

> <JCHEM_LOGP>
-0.13367503833333333

> <ALOGPS_LOGS>
0.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.605312628420254

> <JCHEM_PKA_STRONGEST_BASIC>
-9.240766856996258

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
13.5

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glyoxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000119 (Glyoxylic acid)

HMDB0000119
     RDKit          3D
Glyoxylic acid
  7  6  0  0  0  0  0  0  0  0999 V2000
    1.4768   -0.7904   -0.6827 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0212    0.1407    0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4045    0.3577    0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8334    1.2923    0.8145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3383   -0.4315   -0.5449 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6984    0.7792    0.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6202   -1.3481   -0.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  5  7  1  0
M  END
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PDB for HMDB0000119 (Glyoxylic acid)

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.250   0.228   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.584  -0.542   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -1.250   1.768   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.084  -0.542   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.418   0.228   0.000  0.00  0.00           O+0
CONECT    1    4    3    2                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5                                                       
CONECT    5    4                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0000119 (Glyoxylic acid)

COMPND    HMDB0000119
HETATM    1  O1  UNL     1       1.477  -0.790  -0.683  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.021   0.141   0.015  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.404   0.358   0.112  1.00  0.00           C  
HETATM    4  O2  UNL     1      -0.833   1.292   0.815  1.00  0.00           O  
HETATM    5  O3  UNL     1      -1.338  -0.431  -0.545  1.00  0.00           O  
HETATM    6  H1  UNL     1       1.698   0.779   0.543  1.00  0.00           H  
HETATM    7  H2  UNL     1      -1.620  -1.348  -0.258  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    6
CONECT    3    4    4    5
CONECT    5    7
END
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SMILES for HMDB0000119 (Glyoxylic acid)

OC(=O)C=O
Download

INCHI for HMDB0000119 (Glyoxylic acid)

InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
alpha-Ketoacetic acidChEBI
Formylformic acidChEBI
GlyoxalateChEBI
GlyoxalsaeureChEBI
GlyoxylateChEBI
GlyoxylsaeureChEBI
Oxalaldehydic acidChEBI
Oxoethanoic acidChEBI
a-KetoacetateGenerator
a-Ketoacetic acidGenerator
alpha-KetoacetateGenerator
Α-ketoacetateGenerator
Α-ketoacetic acidGenerator
FormylformateGenerator
Glyoxalic acidGenerator
OxalaldehydateGenerator
OxoethanoateGenerator
OxoacetateHMDB
Oxoacetic acidHMDB
Glyoxylic acid, 2-(14)C-labeledHMDB
Glyoxylic acid, sodium saltHMDB
Glyoxylic acid, sodium salt, 2-(14)C-labeledHMDB
Glyoxylic acid, 14c2-labeledHMDB
Glyoxylic acid, calcium saltHMDB
Glyoxylic acid, sodium salt, 14C-labeledHMDB
Chemical FormulaC2H2O3
Average Molecular Weight74.0355
Monoisotopic Molecular Weight74.00039393
IUPAC Name2-oxoacetic acid
Traditional Nameglyoxylic acid
CAS Registry Number298-12-4
SMILES
OC(=O)C=O
InChI Identifier
InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)
InChI KeyHHLFWLYXYJOTON-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-93 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility224 g/LALOGPS
logP-0.59ALOGPS
logP-0.13ChemAxon
logS0.48ALOGPS
pKa (Strongest Acidic)2.61ChemAxon
pKa (Strongest Basic)-9.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity13.5 m³·mol⁻¹ChemAxon
Polarizability5.35 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]+111.18231661259
DarkChem[M-H]-104.37631661259
AllCCS[M+H]+123.17232859911
AllCCS[M-H]-126.90932859911
DeepCCS[M+H]+119.28230932474
DeepCCS[M-H]-117.38530932474
DeepCCS[M-2H]-152.98930932474
DeepCCS[M+Na]+127.44630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Glyoxylic acidOC(=O)C=O1628.8Standard polar33892256
Glyoxylic acidOC(=O)C=O1101.1Standard non polar33892256
Glyoxylic acidOC(=O)C=O726.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Glyoxylic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C=O855.9Semi standard non polar33892256
Glyoxylic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C=O1113.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Glyoxylic acid GC-MS (1 MEOX; 1 TMS)splash10-03di-3900000000-16bc69e0e9d51e54854e2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Glyoxylic acid GC-MS (Non-derivatized)splash10-03di-3900000000-16bc69e0e9d51e54854e2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glyoxylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0096-9000000000-042540a05be250278f8b2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glyoxylic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9200000000-c60b627ed670285ec37f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glyoxylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glyoxylic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-004l-9000000000-a04bafbf8e0b990094a32014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Glyoxylic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-00di-9000000000-72c34bc34b8c3341442b2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glyoxylic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-00di-9000000000-920a0dc738957201d4ba2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glyoxylic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-00di-9000000000-857c7f2d72c3d4c10dbf2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glyoxylic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-00di-9000000000-9b5825d5d9d8b094fefa2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glyoxylic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-00di-9000000000-de556f03ea428deff5e22012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glyoxylic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-00dl-9000000000-74b253632894213d473c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glyoxylic acid LC-ESI-QQ , negative-QTOFsplash10-00di-9000000000-9b5825d5d9d8b094fefa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glyoxylic acid LC-ESI-QQ , negative-QTOFsplash10-00di-9000000000-de556f03ea428deff5e22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glyoxylic acid LC-ESI-QQ , negative-QTOFsplash10-00dl-9000000000-74b253632894213d473c2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyoxylic acid 10V, Positive-QTOFsplash10-004i-9000000000-a8cc2c89793394fdf9e42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyoxylic acid 20V, Positive-QTOFsplash10-0a6r-9000000000-d20183b08984d4766e8a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyoxylic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-ea9968e3933fd734506c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyoxylic acid 10V, Negative-QTOFsplash10-00di-9000000000-cef8efc477a2500a7ead2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyoxylic acid 20V, Negative-QTOFsplash10-00di-9000000000-3817c0865df6298035382015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyoxylic acid 40V, Negative-QTOFsplash10-00di-9000000000-bb935f857fb5fd08c7e32015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyoxylic acid 10V, Positive-QTOFsplash10-0a4i-9000000000-8f50f0d32d4c40b5b9352021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyoxylic acid 20V, Positive-QTOFsplash10-0a4i-9000000000-b6216caa16afdf3284892021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyoxylic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-aa6a654e73df38a432732021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyoxylic acid 10V, Negative-QTOFsplash10-00di-9000000000-c6f38ec60bcf8724ecd12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyoxylic acid 20V, Negative-QTOFsplash10-00di-9000000000-c6f38ec60bcf8724ecd12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyoxylic acid 40V, Negative-QTOFsplash10-00dl-9000000000-641421c616a0929ce01e2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
  • Peroxisome
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified3.05 (0.25–12.78) uMAdult (>18 years old)MaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified3.28 (2.0-5.32) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
UrineDetected and Quantified1.467 (0.467-3.933) umol/mmol creatinineChildren (1 - 13 years old)Not SpecifiedNormal
    • Geigy Scientific ...
 details
UrineDetected and Quantified1.27 (0.46-3.26) umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified1.88 (0.63-3.22) umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified76 uMAdult (>18 years old)Not SpecifiedTransurethral prostatectomy syndrome details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleInterstitial cystitis details
UrineDetected and Quantified74 umol/mmol creatinineAdult (>18 years old)Male
Primary hyperoxaluria I		 details
UrineDetected and Quantified36-270 umol/mmol creatinineChildren (1-13 years old)BothPrimary hyperoxaluria I details
Associated Disorders and Diseases
Disease References
Transurethral resection of the prostate
  1. Perier C, Mahul P, Molliex S, Auboyer C, Frey J: Progressive changes in glycine and glycine derivatives in plasma and cerebrospinal fluid after transurethral prostatic resection. Clin Chem. 1990 Dec;36(12):2152-3. [PubMed:2253377 ]
Bladder infections
  1. Braundmeier-Fleming A, Russell NT, Yang W, Nas MY, Yaggie RE, Berry M, Bachrach L, Flury SC, Marko DS, Bushell CB, Welge ME, White BA, Schaeffer AJ, Klumpp DJ: Stool-based biomarkers of interstitial cystitis/bladder pain syndrome. Sci Rep. 2016 May 18;6:26083. doi: 10.1038/srep26083. [PubMed:27188581 ]
Primary hyperoxaluria I
  1. Holmgren G, Hornstrom T, Johansson S, Samuelson G: Primary hyperoxaluria (glycolic acid variant): a clinical and genetical investigation of eight cases. Ups J Med Sci. 1978;83(1):65-70. [PubMed:705974 ]
Associated OMIM IDsNone
DrugBank IDDB04343
Phenol Explorer Compound IDNot Available
FooDB IDFDB007244
KNApSAcK IDC00001186
Chemspider ID740
KEGG Compound IDC00048
BioCyc IDGLYOX
BiGG ID33659
Wikipedia LinkGlyoxylic_acid
METLIN ID3213
PubChem Compound760
PDB IDNot Available
ChEBI ID16891
Food Biomarker OntologyNot Available
VMH IDGLX
MarkerDB IDMDB00000055
Good Scents IDNot Available
References
Synthesis ReferenceJie, Yuanping; Song, Zhen. Method for preparing glyoxylic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 5pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lee SH, Kim SO, Chung BC: Gas chromatographic-mass spectrometric determination of urinary oxoacids using O-(2,3,4,5,6-pentafluorobenzyl)oxime-trimethylsilyl ester derivatization and cation-exchange chromatography. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):1-7. [PubMed:9869358 ]
  2. Booth ED, Dofferhoff O, Boogaard PJ, Watson WP: Comparison of the metabolism of ethylene glycol and glycolic acid in vitro by precision-cut tissue slices from female rat, rabbit and human liver. Xenobiotica. 2004 Jan;34(1):31-48. [PubMed:14742135 ]
  3. Naghizadeh F, Barlow D, King J: The reduction of oxo-acids by human tissue extracts. Clin Biochem. 1976 Apr;9(2):65-6. [PubMed:1261003 ]
  4. Borondy PE, Michniewicz BM: Metabolic disposition of isoxicam in man, monkey, dog, and rat. Drug Metab Dispos. 1984 Jul-Aug;12(4):444-51. [PubMed:6148211 ]
  5. Arvesen A, Maehlen J, Rosen L, Aas P: Myointimal hyperplasia and sympathetic reinnervation following local cold injury and rapid rewarming in the rabbit central ear artery. Vasa. 2001 Jul;30(3):176-83. [PubMed:11582947 ]
  6. Motomiya Y, Oyama N, Iwamoto H, Uchimura T, Maruyama I: N epsilon-(carboxymethyl)lysine in blood from maintenance hemodialysis patients may contribute to dialysis-related amyloidosis. Kidney Int. 1998 Oct;54(4):1357-66. [PubMed:9767556 ]
  7. Holmes E, Foxall PJ, Spraul M, Farrant RD, Nicholson JK, Lindon JC: 750 MHz 1H NMR spectroscopy characterisation of the complex metabolic pattern of urine from patients with inborn errors of metabolism: 2-hydroxyglutaric aciduria and maple syrup urine disease. J Pharm Biomed Anal. 1997 Jul;15(11):1647-59. [PubMed:9260660 ]
  8. Mentasti E, Savigliano M, Marangella M, Petrarulo M, Linari F: High-performance liquid chromatographic determination of glyoxylic acid and other carbonyl compounds in urine. J Chromatogr. 1987 Jul 3;417(2):253-60. [PubMed:3654878 ]
  9. Bruzzese FJ, Dix JA, Rava RP, Cerny LC: Resonance Raman spectroscopy of chemically modified hemoglobins. Biomater Artif Cells Artif Organs. 1990;18(2):143-56. [PubMed:2369642 ]
  10. Schmitt A, Gasic-Milenkovic J, Schmitt J: Characterization of advanced glycation end products: mass changes in correlation to side chain modifications. Anal Biochem. 2005 Nov 1;346(1):101-6. Epub 2005 Aug 15. [PubMed:16168380 ]
  11. Tainio H, Vaalasti A, Rechardt L: The distribution of sympathetic adrenergic, tyrosine hydroxylase- and neuropeptide Y-immunoreactive nerves in human axillary sweat glands. Histochemistry. 1986;85(2):117-20. [PubMed:2875046 ]
  12. Davis WL, Goodman DB: Evidence for the glyoxylate cycle in human liver. Anat Rec. 1992 Dec;234(4):461-8. [PubMed:1456449 ]
  13. Arvesen A, Maehlen J, Rosen L, Aas P: Early and late functional and histopathological perturbations in the rabbit ear-artery following local cold injury. Vasa. 1999 May;28(2):85-94. [PubMed:10409918 ]
  14. Popov VN, Moskalev EA, Shevchenko MIu, Eprintsev AT: [Comparative analysis of the glyoxylate cycle clue enzyme isocitrate lyases from organisms of different systemic groups]. Zh Evol Biokhim Fiziol. 2005 Nov-Dec;41(6):507-13. [PubMed:16396466 ]

Enzymes

Enzyme Details
1. D-amino-acid oxidase
General function:
Involved in D-amino-acid oxidase activity
Specific function:
Regulates the level of the neuromodulator D-serine in the brain. Has high activity towards D-DOPA and contributes to dopamine synthesis. Could act as a detoxifying agent which removes D-amino acids accumulated during aging. Acts on a variety of D-amino acids with a preference for those having small hydrophobic side chains followed by those bearing polar, aromatic, and basic groups. Does not act on acidic amino acids.
Gene Name:
DAO
Uniprot ID:
P14920
Molecular weight:
39473.75
Reactions
Glycine + Water + Oxygen → Glyoxylic acid + Ammonia + Hydrogen peroxidedetails
Enzyme Details
2. Peptidyl-glycine alpha-amidating monooxygenase
General function:
Involved in monooxygenase activity
Specific function:
Bifunctional enzyme that catalyzes 2 sequential steps in C-terminal alpha-amidation of peptides. The monooxygenase part produces an unstable peptidyl(2-hydroxyglycine) intermediate that is dismutated to glyoxylate and the corresponding desglycine peptide amide by the lyase part. C-terminal amidation of peptides such as neuropeptides is essential for full biological activity.
Gene Name:
PAM
Uniprot ID:
P19021
Molecular weight:
108402.425
Reactions
Peptidylamidoglycolate → peptidyl amide + Glyoxylic aciddetails
Enzyme Details
3. Glyoxylate reductase/hydroxypyruvate reductase
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Enzyme with hydroxy-pyruvate reductase, glyoxylate reductase and D-glycerate dehydrogenase enzymatic activities. Reduces hydroxypyruvate to D-glycerate, glyoxylate to glycolate oxidizes D-glycerate to hydroxypyruvate.
Gene Name:
GRHPR
Uniprot ID:
Q9UBQ7
Molecular weight:
35667.875
Reactions
Glycolic acid + NADP → Glyoxylic acid + NADPHdetails
Glycolic acid + NADP → Glyoxylic acid + NADPH + Hydrogen Iondetails
Enzyme Details
4. Alanine--glyoxylate aminotransferase 2, mitochondrial
General function:
Involved in transaminase activity
Specific function:
Can metabolize asymmetric dimethylarginine (ADMA) via transamination to alpha-keto-delta-(NN-dimethylguanidino) valeric acid (DMGV). ADMA is a potent inhibitor of nitric-oxide (NO) synthase, and this activity provides mechanism through which the kidney regulates blood pressure.
Gene Name:
AGXT2
Uniprot ID:
Q9BYV1
Molecular weight:
57155.905
Reactions
L-Alanine + Glyoxylic acid → Pyruvic acid + Glycinedetails
Glycine + Oxoglutaric acid → Glyoxylic acid + L-Glutamic aciddetails
Enzyme Details
5. Hydroxyacid oxidase 1
General function:
Involved in FMN binding
Specific function:
Has 2-hydroxyacid oxidase activity. Most active on the 2-carbon substrate glycolate, but is also active on 2-hydroxy fatty acids, with high activity towards 2-hydroxy palmitate and 2-hydroxy octanoate.
Gene Name:
HAO1
Uniprot ID:
Q9UJM8
Molecular weight:
40923.945
Reactions
Glycolic acid + Oxygen → Glyoxylic acid + Hydrogen peroxidedetails
Enzyme Details
6. Hydroxyacid oxidase 2
General function:
Involved in FMN binding
Specific function:
Catalyzes the oxidation of L-alpha-hydroxy acids as well as, more slowly, that of L-alpha-amino acids.
Gene Name:
HAO2
Uniprot ID:
Q9NYQ3
Molecular weight:
38838.35
Reactions
Glycolic acid + Oxygen → Glyoxylic acid + Hydrogen peroxidedetails
Enzyme Details
7. Serine--pyruvate aminotransferase
General function:
Involved in metabolic process
Specific function:
Not Available
Gene Name:
AGXT
Uniprot ID:
P21549
Molecular weight:
43009.535
Reactions
L-Alanine + Glyoxylic acid → Pyruvic acid + Glycinedetails
Glycine + Oxoglutaric acid → Glyoxylic acid + L-Glutamic aciddetails
L-Serine + Glyoxylic acid → Hydroxypyruvic acid + Glycinedetails
Enzyme Details
8. Kynurenine--oxoglutarate transaminase 3
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). May catalyze the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond (By similarity). Has transaminase activity towards L-kynurenine, tryptophan, phenylalanine, serine, cysteine, methionine, histidine, glutamine and asparagine with glyoxylate as an amino group acceptor (in vitro). Has lower activity with 2-oxoglutarate as amino group acceptor (in vitro) (By similarity).
Gene Name:
CCBL2
Uniprot ID:
Q6YP21
Molecular weight:
51399.855
Reactions
L-Kynurenine + Glyoxylic acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glycinedetails
Enzyme Details
9. Probable 4-hydroxy-2-oxoglutarate aldolase, mitochondrial
General function:
Not Available
Specific function:
Catalyzes the final step in the metabolic pathway of hydroxyproline (Probable).
Gene Name:
HOGA1
Uniprot ID:
Q86XE5
Molecular weight:
17953.475
Reactions
4-Hydroxy-2-oxoglutaric acid → Pyruvic acid + Glyoxylic aciddetails

Transporters

Enzyme Details
1. Monocarboxylate transporter 4
General function:
Involved in transmembrane transport
Specific function:
Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
Gene Name:
SLC16A3
Uniprot ID:
O15427
Molecular weight:
49468.9
References
  1. Manning Fox JE, Meredith D, Halestrap AP: Characterisation of human monocarboxylate transporter 4 substantiates its role in lactic acid efflux from skeletal muscle. J Physiol. 2000 Dec 1;529 Pt 2:285-93. [PubMed:11101640 ]