Record Information
Version2.0
Creation Date2012-05-31 14:10:18 -0600
Update Date2015-06-03 15:54:57 -0600
Secondary Accession Numbers
  • ECMDB06938
Identification
Name:Tartronate semialdehyde
DescriptionTartronate semialdehyde is an intermediate in ascorbate and aldarate as well as glyoxylate and dicarboxylate metabolism. It is generated from 2-dehydro-3-deoxy-D-glucarate and 5-dehydro-4-deoxy-D-glucarate via the enzyme 2-dehydro-3-deoxyglucarate aldolase [EC:4.1.2.20].
Structure
Thumb
Synonyms:
  • 2-Hydroxy-3-oxopropanoate
  • 2-Hydroxy-3-oxopropanoic acid
  • Hydroxymalonaldehydate
  • Hydroxymalonaldehydic acid
  • Tartronate-S-ald
  • Tartronic acid semialdehyde
  • Tartronic acid-S-ald
  • Tartronic semialdehyde
Chemical Formula:C3H4O4
Weight:Average: 104.0615
Monoisotopic: 104.010958616
InChI Key:QWBAFPFNGRFSFB-UHFFFAOYSA-N
InChI:InChI=1S/C3H4O4/c4-1-2(5)3(6)7/h1-2,5H,(H,6,7)
CAS number:Not Available
IUPAC Name:2-hydroxy-3-oxopropanoic acid
Traditional IUPAC Name:tartronate semialdehyde
SMILES:OC(C=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Alpha-hydroxy acid
  • Hydroxy acid
  • 1,3-dicarbonyl compound
  • Monosaccharide
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Aldehyde
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility327 g/LALOGPS
logP-0.92ALOGPS
logP-1.2ChemAxon
logS0.5ALOGPS
pKa (Strongest Acidic)3.04ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.4 m³·mol⁻¹ChemAxon
Polarizability8.1 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Tartronate semialdehyde + Hydrogen ion + NADH <> Glyceric acid + NAD
2 Glyoxylic acid + Hydrogen ion <> Tartronate semialdehyde + Carbon dioxide
Hydroxypyruvic acid <> Tartronate semialdehyde
5-Dehydro-4-deoxy-D-glucarate > Tartronate semialdehyde + Pyruvic acid
2 Glyoxylic acid <> Tartronate semialdehyde + Carbon dioxide
Glyceric acid + NAD <> Tartronate semialdehyde + NADH + Hydrogen ion
Glyceric acid + NADP <> Tartronate semialdehyde + NADPH + Hydrogen ion
5-Dehydro-4-deoxy-D-glucarate <> Pyruvic acid + Tartronate semialdehyde
Tartronate semialdehyde + Pyruvic acid <> 2-Dehydro-3-deoxy-D-glucarate
Hydrogen ion + Glyoxylic acid > Carbon dioxide + Tartronate semialdehyde
NAD(P)<sup>+</sup> + Glyceric acid < NAD(P)H + Tartronate semialdehyde + Hydrogen ion
2-Dehydro-3-deoxy-D-glucarate > Pyruvic acid + Tartronate semialdehyde
Glyceric acid + NAD(P)(+) > Tartronate semialdehyde + NAD(P)H
2 Glyoxylic acid > Tartronate semialdehyde + Carbon dioxide
Hydroxypyruvic acid > Tartronate semialdehyde
Glyceric acid + NAD + NADP <> Tartronate semialdehyde + NADH + NADPH + Hydrogen ion
5-dehydro-4-deoxy-D-glucarate(2−) > Pyruvic acid + Tartronate semialdehyde
Tartronate semialdehyde + Hydrogen ion + NADPH + NADPH > NADP + Glyceric acid
2 Glyoxylic acid + Hydrogen ion > Carbon dioxide + Tartronate semialdehyde
Tartronate semialdehyde + NADH + Hydrogen ion > NAD + Glyceric acid
Tartronate semialdehyde + Hydrogen ion + NADH <> Glyceric acid + NAD
Hydroxypyruvic acid <> Tartronate semialdehyde
2 Glyoxylic acid + Hydrogen ion <> Tartronate semialdehyde + Carbon dioxide
Hydroxypyruvic acid <> Tartronate semialdehyde
SMPDB Pathways:
glycolate and glyoxylate degradationPW000827 ThumbThumb?image type=greyscaleThumb?image type=simple
glycolate and glyoxylate degradation IIPW002021 ThumbThumb?image type=greyscaleThumb?image type=simple
superpathway of D-glucarate and D-galactarate degradationPW000795 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-a60f01ed6b22e180e045View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ac-9440000000-afd8c910b7b1f49d2e62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-9500000000-f812e132ac3b2e736637View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-ceca81538df1215a85f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4u-9000000000-9d63dd3b34de8e05e06eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-6900000000-e9845cd50bf0a0e27a71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc0-9200000000-a8bdb790ea1f2037fb61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-3b924f51c31faa2a9e9aView in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16992
HMDB IDHMDB06938
Pubchem Compound ID1122
Kegg IDC01146
ChemSpider ID1090
Wikipedia IDNot Available
BioCyc IDTARTRONATE-S-ALD
EcoCyc IDTARTRONATE-S-ALD

Enzymes

General function:
Involved in 3-hydroxyisobutyrate dehydrogenase activity
Specific function:
(R)-glycerate + NAD(P)(+) = 2-hydroxy-3- oxopropanoate + NAD(P)H
Gene Name:
garR
Uniprot ID:
P0ABQ2
Molecular weight:
30427
Reactions
D-glycerate + NAD(P)(+) = 2-hydroxy-3-oxopropanoate + NAD(P)H.
General function:
Involved in tartronate-semialdehyde synthase activity
Specific function:
Catalyzes the condensation of two molecules of glyoxylate to give 2-hydroxy-3-oxopropanoate (also termed tartronate semialdehyde)
Gene Name:
gcl
Uniprot ID:
P0AEP7
Molecular weight:
64731
Reactions
2 glyoxylate = tartronate semialdehyde + CO(2).
General function:
Involved in carbon-carbon lyase activity
Specific function:
Catalyzes the reversible retro-aldol cleavage of both 5- keto-4-deoxy-D-glucarate and 2-keto-3-deoxy-D-glucarate to pyruvate and tartronic semialdehyde
Gene Name:
garL
Uniprot ID:
P23522
Molecular weight:
27384
Reactions
5-dehydro-4-deoxy-D-glucarate = pyruvate + tartronate semialdehyde.
2-dehydro-3-deoxy-D-glucarate = pyruvate + tartronate semialdehyde.
General function:
Carbohydrate transport and metabolism
Specific function:
Catalyzes the reversible isomerization between hydroxypyruvate and 2-hydroxy-3-oxopropanoate (also termed tartronate semialdehyde)
Gene Name:
hyi
Uniprot ID:
P30147
Molecular weight:
29377
Reactions
Hydroxypyruvate = 2-hydroxy-3-oxopropanoate.
General function:
Involved in 3-hydroxyisobutyrate dehydrogenase activity
Specific function:
(R)-glycerate + NAD(P)(+) = 2-hydroxy-3- oxopropanoate + NAD(P)H
Gene Name:
glxR
Uniprot ID:
P77161
Molecular weight:
30800
Reactions
D-glycerate + NAD(P)(+) = 2-hydroxy-3-oxopropanoate + NAD(P)H.