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Record Information
Version	2.0
Creation Date	2012-05-31 14:34:10 -0600
Update Date	2015-06-03 17:19:35 -0600
Secondary Accession Numbers	ECMDB20227
Identification
Name:	2-Hydroxymalonate
Description	2-hydroxymalonate is a member of the chemical class known as Sugar Acids and Derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group. 2-hydroxymalonate is involved in d-glycerate biosynthesis. Further evidence for identification as tartronate semialdehyde reductase is the observation that the coding region for this protein is directly preceded by genes coding for hydroxypyruvate isomerase and glyoxylate carboligase, two enzymes that synthesize tartronate semialdehyde, producing an operon clearly designed for d-glycerate biosynthesis from tartronate semialdehyde. (PMID 10978349)
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xb48ee194> Close
Synonyms:	2-Hydroxymalonic acid 2-Hydroxypropanedioate 2-Hydroxypropanedioic acid Hydroxy-Malonate Hydroxy-Malonic acid Hydroxy-Propanedioate Hydroxy-Propanedioic acid Hydroxymalonate Hydroxymalonate(2-) Hydroxymalonic acid Hydroxymalonic acid(2-) Hydroxypropanedioate Hydroxypropanedioic acid Tartronate Tartronic acid TTN
Chemical Formula:	C3H2O5
Weight:	Average: 118.045 Monoisotopic: 117.990223174
InChI Key:	ROBFUDYVXSDBQM-UHFFFAOYSA-L
InChI:	InChI=1S/C3H4O5/c4-1(2(5)6)3(7)8/h1,4H,(H,5,6)(H,7,8)/p-2
CAS number:	80-69-3
IUPAC Name:	2-hydroxypropanedioate
Traditional IUPAC Name:	tartronate
SMILES:	OC(C([O-])=O)C([O-])=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Sugar acids and derivatives
Alternative Parents	Monosaccharides Dicarboxylic acids and derivatives 1,3-dicarbonyl compounds Secondary alcohols Carboxylic acids Organic oxides Hydrocarbon derivatives Organic anions
Substituents	Sugar acid 1,3-dicarbonyl compound Monosaccharide Dicarboxylic acid or derivatives Secondary alcohol Carboxylic acid Carboxylic acid derivative Organic oxide Hydrocarbon derivative Carbonyl group Alcohol Organic anion Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	dicarboxylic acid dianion (CHEBI:17649 ) a small molecule (HYDROXYMALONATE )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	157 °C
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 542 g/L ALOGPS logP -0.92 ALOGPS logP -1 ChemAxon logS 0.55 ALOGPS pKa (Strongest Acidic) 2.16 ChemAxon pKa (Strongest Basic) -4.9 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 100.49 Ų ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 42 m³·mol⁻¹ ChemAxon Polarizability 8.16 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:
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-014i-0900000000-29963ba4d2404024a214 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0a4i-2900000000-18b6feaa599cdf529d3e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-052r-9400000000-5bb345ec907d4ce0e358 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-016r-7900000000-0ecf421c4ce21679443e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00or-9700000000-60ddfb8dcb4ad9c5948b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-056r-9000000000-068bb2ae87dfe07231cb View in MoNA 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 1D NMR 1H 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 Njau, R. K., Herndon, C. A., Hawes, J. W. (2000). "Novel beta -hydroxyacid dehydrogenases in Escherichia coli and Haemophilus influenzae." J Biol Chem 275:38780-38786. Pubmed: 10978349 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 16513 HMDB ID Not Available Pubchem Compound ID 44 Kegg ID C02287 ChemSpider ID 43 Wikipedia ID Tartronic acid BioCyc ID HYDROXYMALONATE EcoCyc ID HYDROXYMALONATE