Record Information
Version 1.0
Update Date 1/22/2018 12:54:53 PM
Metabolite IDPAMDB000707
Identification
Name: Tartronate semialdehyde
Description:Tartronate 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
Average Molecular Weight: 104.0615
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Hydroxy acids and derivatives
Sub ClassAlpha hydroxy acids and derivatives
Direct Parent Alpha hydroxy acids and derivatives
Alternative Parents
Substituents
  • 1,3-dicarbonyl compound
  • Monosaccharide
  • Alpha-hydroxy acid
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility327.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.4 m3·mol-1ChemAxon
Polarizability8.1 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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