Identification

Name
Glyoxylic acid
Accession Number
DB04343  (EXPT01614)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
JQ39C92HH6
CAS number
298-12-4
Weight
Average: 74.0355
Monoisotopic: 74.00039393
Chemical Formula
C2H2O3
InChI Key
HHLFWLYXYJOTON-UHFFFAOYSA-N
InChI
InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)
IUPAC Name
2-oxoacetic acid
SMILES
OC(=O)C=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UMalate synthase GNot AvailableEscherichia coli (strain K12)
UIsocitrate lyaseNot AvailableMycobacterium tuberculosis
UMalate synthase GNot AvailableMycobacterium tuberculosis
UPutative regulator of ribonuclease activityNot AvailableMycobacterium tuberculosis
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Hyperglycinemia, non-ketoticDisease
Pyruvate Carboxylase DeficiencyDisease
3-Phosphoglycerate dehydrogenase deficiencyDisease
Alanine MetabolismMetabolic
Lactic AcidemiaDisease
Non Ketotic HyperglycinemiaDisease
Primary Hyperoxaluria Type IDisease
Dimethylglycine Dehydrogenase DeficiencyDisease
Glycine and Serine MetabolismMetabolic
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)Disease
Dimethylglycine Dehydrogenase DeficiencyDisease
SarcosinemiaDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB00119
KEGG Compound
C00048
PubChem Compound
760
PubChem Substance
46507705
ChemSpider
740
BindingDB
19472
ChEBI
16891
ChEMBL
CHEMBL1162545
HET
GLV
PDB Entries
1d8c / 1f8i / 1n8i / 1n8w / 1nxj / 1yqc / 2bkw / 2et1 / 2ete / 2hcj
show 17 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)98 °CPhysProp
pKa3.3 (at 25 °C)DEAN,JA (1985)
Predicted Properties
PropertyValueSource
Water Solubility224.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity13.5 m3·mol-1ChemAxon
Polarizability5.35 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9438
Blood Brain Barrier+0.9511
Caco-2 permeable-0.6479
P-glycoprotein substrateNon-substrate0.8635
P-glycoprotein inhibitor INon-inhibitor0.9774
P-glycoprotein inhibitor IINon-inhibitor0.9786
Renal organic cation transporterNon-inhibitor0.9556
CYP450 2C9 substrateNon-substrate0.8352
CYP450 2D6 substrateNon-substrate0.9403
CYP450 3A4 substrateNon-substrate0.8286
CYP450 1A2 substrateNon-inhibitor0.9697
CYP450 2C9 inhibitorNon-inhibitor0.9683
CYP450 2D6 inhibitorNon-inhibitor0.9619
CYP450 2C19 inhibitorNon-inhibitor0.9881
CYP450 3A4 inhibitorNon-inhibitor0.9892
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9961
Ames testNon AMES toxic0.7673
CarcinogenicityCarcinogens 0.5
BiodegradationReady biodegradable0.8937
Rat acute toxicity1.5816 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9925
hERG inhibition (predictor II)Non-inhibitor0.9874
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)GC-MSsplash10-03di-3900000000-16bc69e0e9d51e54854e
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-03di-3900000000-16bc69e0e9d51e54854e
Mass Spectrum (Electron Ionization)MSsplash10-004l-9000000000-a04bafbf8e0b990094a3
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-00di-9000000000-72c34bc34b8c3341442b
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-00di-9000000000-920a0dc738957201d4ba
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-00di-9000000000-857c7f2d72c3d4c10dbf
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-00di-9000000000-9b5825d5d9d8b094fefa
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-00di-9000000000-de556f03ea428deff5e2
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-00dl-9000000000-74b253632894213d473c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-a8cc2c89793394fdf9e4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-9000000000-d20183b08984d4766e8a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-ea9968e3933fd734506c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-cef8efc477a2500a7ead
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-3817c0865df629803538
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-bb935f857fb5fd08c7e3
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-9000000000-9b5825d5d9d8b094fefa
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-9000000000-de556f03ea428deff5e2
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00dl-9000000000-74b253632894213d473c
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as carboxylic acids. These are compounds containing a carboxylic acid group with the formula -C(=O)OH.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Carboxylic acids
Direct Parent
Carboxylic acids
Alternative Parents
Monocarboxylic acids and derivatives / Short-chain aldehydes / Organic oxides / Hydrocarbon derivatives
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 Framework
Aliphatic acyclic compounds
External Descriptors
2-oxo monocarboxylic acid, aldehydic acid (CHEBI:16891)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Involved in the glycolate utilization. Catalyzes the condensation and subsequent hydrolysis of acetyl-coenzyme A (acetyl-CoA) and glyoxylate to form malate and CoA.
Gene Name
glcB
Uniprot ID
P37330
Uniprot Name
Malate synthase G
Molecular Weight
80487.88 Da
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]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Involved in the persistence and virulence of M.tuberculosis. Catalyzes the reversible formation of succinate and glyoxylate from isocitrate, a key step of the glyoxylate cycle, which operates as an anaplerotic route for replenishing the tricarboxylic acid cycle during growth on fatty acid substrates (PubMed:10932251, PubMed:10963599, PubMed:18275086, PubMed:24354272). It could also catalyze the formation of pyruvate and succinate from 2-methylisocitrate, a key step in the methylcitrate cycle (propionate degradation route) (By similarity).
Specific Function
Isocitrate lyase activity
Gene Name
icl
Uniprot ID
P9WKK7
Uniprot Name
Isocitrate lyase
Molecular Weight
47086.255 Da
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]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Involved in the glycolate utilization. Catalyzes the condensation and subsequent hydrolysis of acetyl-coenzyme A (acetyl-CoA) and glyoxylate to form malate and CoA.
Specific Function
Coenzyme binding
Gene Name
glcB
Uniprot ID
P9WK17
Uniprot Name
Malate synthase G
Molecular Weight
80402.24 Da
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]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Catalyzes the aldol cleavage of 4-hydroxy-4-methyl-2-oxoglutarate (HMG) into 2 molecules of pyruvate. Also contains a secondary oxaloacetate (OAA) decarboxylase activity due to the common pyruvate enolate transition state formed following C-C bond cleavage in the retro-aldol and decarboxylation reactions (By similarity).
Specific Function
4-hydroxy-4-methyl-2-oxoglutarate aldolase activity
Gene Name
rraA
Uniprot ID
P9WGY3
Uniprot Name
Putative 4-hydroxy-4-methyl-2-oxoglutarate aldolase
Molecular Weight
16235.24 Da
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]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Symporter activity
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...
Gene Name
SLC16A3
Uniprot ID
O15427
Uniprot Name
Monocarboxylate transporter 4
Molecular Weight
49468.9 Da
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]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:40