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Record Information
Version	2.0
Creation Date	2012-05-31 14:10:18 -0600
Update Date	2015-06-03 15:54:57 -0600
Secondary Accession Numbers	ECMDB06938
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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xb2f0c208> Close
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.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Monosaccharides
Alternative Parents	Alpha hydroxy acids and derivatives 1,3-dicarbonyl compounds Alpha-hydroxyaldehydes Secondary alcohols Monocarboxylic acids and derivatives Carboxylic acids Short-chain aldehydes Organic oxides Hydrocarbon derivatives
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 Framework	Aliphatic acyclic compounds
External Descriptors	3-oxo monocarboxylic acid (CHEBI:16992 ) 2-hydroxy monocarboxylic acid (CHEBI:16992 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 327 g/L ALOGPS logP -0.92 ALOGPS logP -1.2 ChemAxon logS 0.5 ALOGPS pKa (Strongest Acidic) 3.04 ChemAxon pKa (Strongest Basic) -4.5 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 74.6 Ų ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 19.4 m³·mol⁻¹ ChemAxon Polarizability 8.1 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
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 degradation PW000827 glycolate and glyoxylate degradation II PW002021 superpathway of D-glucarate and D-galactarate degradation PW000795
KEGG Pathways:	Ascorbate and aldarate metabolism ec00053 Glyoxylate and dicarboxylate metabolism ec00630 Metabolic pathways eco01100
EcoCyc Pathways:	D-glucarate degradation I GLUCARDEG-PWY D-galactarate degradation I GALACTARDEG-PWY glycolate and glyoxylate degradation I GLYCOLATEMET-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-052f-9000000000-a60f01ed6b22e180e045 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-00ac-9440000000-afd8c910b7b1f49d2e62 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0a4r-9500000000-f812e132ac3b2e736637 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0a4r-9100000000-ceca81538df1215a85f7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4u-9000000000-9d63dd3b34de8e05e06e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0udi-6900000000-e9845cd50bf0a0e27a71 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0pc0-9200000000-a8bdb790ea1f2037fb61 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-9000000000-3b924f51c31faa2a9e9a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0zi3-9300000000-607c03f7e8cd6716e11d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0006-9000000000-f440bef0a5740a66164c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-9000000000-87a1803920534b6e560e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0a4u-9100000000-46786392dfaa1185c663 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-066u-9000000000-5de8c87d45a4af20988e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0006-9000000000-034038c78b2eda187f41 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer
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
Links
External Links:	Resource Link CHEBI ID 16992 HMDB ID HMDB06938 Pubchem Compound ID 1122 Kegg ID C01146 ChemSpider ID 1090 Wikipedia ID Not Available BioCyc ID TARTRONATE-S-ALD EcoCyc ID TARTRONATE-S-ALD

Enzymes