Record Information
Version1.0
Created at2020-04-17 18:38:28 UTC
Updated at2020-12-07 19:10:58 UTC
CannabisDB IDCDB004804
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameGlyoxylic acid
DescriptionGlyoxylic acid, also known as a-ketoacetate or glyoxalate, 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. Glyoxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). A 2-oxo monocarboxylic acid that is acetic acid bearing an oxo group at the alpha carbon atom. Glyoxylic acid exists in all living species, ranging from bacteria to humans. L-alanine and glyoxylic acid can be biosynthesized from glycine and pyruvic acid through its interaction with the enzyme serine--pyruvate aminotransferase. In humans, glyoxylic acid is involved in the metabolic disorder called the dimethylglycine dehydrogenase deficiency pathway. Outside of the human body, Glyoxylic acid has been detected, but not quantified in, tamarinds. This could make glyoxylic acid a potential biomarker for the consumption of these foods. Glyoxylic acid is a potentially toxic compound. Glyoxylic acid, with regard to humans, has been found to be associated with several diseases such as bladder infections and transurethral resection of the prostate; glyoxylic acid has also been linked to the inborn metabolic disorder primary hyperoxaluria I. Glyoxylic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
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 Weight74.04
Monoisotopic Molecular Weight74.0004
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

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-93 °CNot Available
Boiling Point111 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004l-9000000000-a04bafbf8e0b990094a3Spectrum
GC-MSGlyoxylic acid, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-03di-3900000000-16bc69e0e9d51e54854eSpectrum
GC-MSGlyoxylic acid, non-derivatized, GC-MS Spectrumsplash10-03di-3900000000-16bc69e0e9d51e54854eSpectrum
Predicted GC-MSGlyoxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0096-9000000000-042540a05be250278f8bSpectrum
Predicted GC-MSGlyoxylic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fr-9200000000-c60b627ed670285ec37fSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-9000000000-72c34bc34b8c3341442bSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-9000000000-920a0dc738957201d4baSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00di-9000000000-857c7f2d72c3d4c10dbfSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-9000000000-9b5825d5d9d8b094fefaSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-9000000000-de556f03ea428deff5e2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00dl-9000000000-74b253632894213d473cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-9b5825d5d9d8b094fefaSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-de556f03ea428deff5e2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dl-9000000000-74b253632894213d473cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-a8cc2c89793394fdf9e4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9000000000-d20183b08984d4766e8aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-ea9968e3933fd734506cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-cef8efc477a2500a7eadSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-3817c0865df629803538Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-bb935f857fb5fd08c7e3Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
D-amino-acid oxidaseDAO12q24P14920 details
Peptidyl-glycine alpha-amidating monooxygenasePAM5q14-q21P19021 details
Glyoxylate reductase/hydroxypyruvate reductaseGRHPR9q12Q9UBQ7 details
Alanine--glyoxylate aminotransferase 2, mitochondrialAGXT25p13Q9BYV1 details
Hydroxyacid oxidase 1HAO120p12Q9UJM8 details
Hydroxyacid oxidase 2HAO21p13.3-p13.1Q9NYQ3 details
Serine--pyruvate aminotransferaseAGXT2q37.3P21549 details
Kynurenine--oxoglutarate transaminase 3CCBL21p22.2Q6YP21 details
Probable 4-hydroxy-2-oxoglutarate aldolase, mitochondrialHOGA110q24.2Q86XE5 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Monocarboxylate transporter 4SLC16A317q25O15427 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Peptidyl-glycine alpha-amidating monooxygenasePAM5q14-q21P19021 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000119
DrugBank IDDB04343
Phenol Explorer Compound IDNot Available
FoodDB IDFDB007244
KNApSAcK IDC00001186
Chemspider ID740
KEGG Compound IDC00048
BioCyc IDGLYOX
BiGG ID33659
Wikipedia LinkGlyoxylic_acid
METLIN ID3213
PubChem Compound760
PDB IDNot Available
ChEBI ID16891
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 11 proteins in total.

Enzymes

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
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
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
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
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
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
General function:
Involved in metabolic process
Specific function:
Not Available
Gene Name:
AGXT
Uniprot ID:
P21549
Molecular weight:
43009.535
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
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

Transporters

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

Only showing the first 10 proteins. There are 11 proteins in total.