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Record Information
Version	2.0
Creation Date	2012-05-31 14:27:12 -0600
Update Date	2015-06-03 17:19:18 -0600
Secondary Accession Numbers	ECMDB20095
Identification
Name:	4-Phospho-D-erythronate
Description	4-phospho-D-erythronate is a member of the chemical class known as Beta Hydroxy Acids and Derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. To establish a possible role of E4PDH in pyridoxal 5'-phosphate biosynthesis, we showed that 4-phosphoerythronate is a likely substrate for the 2-hydroxy-acid dehydrogenase encoded by the pdxB gene. (PMID 7751290)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xac43adbc> Close
Synonyms:	(2R,3S)-2,3-dihydroxy-4-phosphonooxybutanoate (2R,3S)-2,3-dihydroxy-4-phosphonooxybutanoic acid 2,3-Dihydroxy-4-phosphonooxybutanoate 2,3-Dihydroxy-4-phosphonooxybutanoic acid 4-Phospho-D-erythronate 4-Phospho-D-erythronic acid 4-Phosphoerythronate 4-Phosphoerythronic acid D-4-Phosphoerythronate D-4-Phosphoerythronic Acid D-Erythronate-4-phosphate D-Erythronate-4P D-Erythronic acid-4-phosphoric acid D-Erythronic acid-4P Ery4P Erythronate-4P Erythronic acid-4P
Chemical Formula:	C4H9O8P
Weight:	Average: 216.0832 Monoisotopic: 216.003503776
InChI Key:	ZCZXOHUILRHRQJ-PWNYCUMCSA-N
InChI:	InChI=1S/C4H9O8P/c5-2(3(6)4(7)8)1-12-13(9,10)11/h2-3,5-6H,1H2,(H,7,8)(H2,9,10,11)/t2-,3-/m1/s1
CAS number:	Not Available
IUPAC Name:	(2R,3R)-2,3-dihydroxy-4-(phosphonooxy)butanoic acid
Traditional IUPAC Name:	4-phospho-D-erythronic acid
SMILES:	[H][C@@](O)(COP(O)(O)=O)[C@@]([H])(O)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Monosaccharide phosphates
Alternative Parents	Sugar acids and derivatives Short-chain hydroxy acids and derivatives Monoalkyl phosphates Beta hydroxy acids and derivatives Fatty acids and conjugates Alpha hydroxy acids and derivatives Secondary alcohols 1,2-diols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	Monosaccharide phosphate Beta-hydroxy acid Short-chain hydroxy acid Sugar acid Monoalkyl phosphate Phosphoric acid ester Organic phosphoric acid derivative Hydroxy acid Alkyl phosphate Alpha-hydroxy acid Fatty acid Secondary alcohol 1,2-diol Monocarboxylic acid or derivatives Carboxylic acid Carboxylic acid derivative Alcohol Organic oxide Carbonyl group Hydrocarbon derivative Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	4-phosphoerythronic acid (CHEBI:49003 )
Physical Properties
State:	Not Available
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 19.6 g/L ALOGPS logP -2.3 ALOGPS logP -2.3 ChemAxon logS -1 ALOGPS pKa (Strongest Acidic) 1.47 ChemAxon pKa (Strongest Basic) -3.6 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 144.52 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 37.22 m³·mol⁻¹ ChemAxon Polarizability 15.98 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:	D-Erythrose 4-phosphate + Water + NAD <> 4-Phospho-D-erythronate +2 Hydrogen ion + NADH 4-Phospho-D-erythronate + NAD <> Hydrogen ion + NADH + 2-Oxo-3-hydroxy-4-phosphobutanoic acid D-Erythrose 4-phosphate + NAD + Water <> 4-Phospho-D-erythronate + NADH + Hydrogen ion D-Erythrose 4-phosphate + Water + NAD > 4-Phospho-D-erythronate + NADH + Hydrogen ion 4-Phospho-D-erythronate + NAD > Hydrogen ion + 2-Oxo-3-hydroxy-4-phosphobutanoic acid + NADH D-Erythrose 4-phosphate + NAD + Water > 4-Phospho-D-erythronate + NADH 4-Phospho-D-erythronate + NAD > 2-Oxo-3-hydroxy-4-phosphobutanoic acid + NADH D-Erythrose 4-phosphate + NAD + Water > 4-Phospho-D-erythronate + NADH +2 Hydrogen ion D-Erythrose 4-phosphate + Water + NAD <>4 4-Phospho-D-erythronate +2 Hydrogen ion + NADH 4 4-Phospho-D-erythronate + NAD <> Hydrogen ion + NADH +2 2-Oxo-3-hydroxy-4-phosphobutanoic acid 4 4-Phospho-D-erythronate + NAD <> Hydrogen ion + NADH +2 2-Oxo-3-hydroxy-4-phosphobutanoic acid D-Erythrose 4-phosphate + Water + NAD <>4 4-Phospho-D-erythronate +2 Hydrogen ion + NADH
SMPDB Pathways:	Vitamin B6 1430936196 PW000891
KEGG Pathways:	Metabolic pathways eco01100 Vitamin B6 metabolism ec00750
EcoCyc Pathways:	pyridoxal 5'-phosphate biosynthesis I PYRIDOXSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0002-9300000000-6fa3e5b82781cb309499 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00kb-2920000000-a5fad921f0528d94b501 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-006w-5900000000-2a302dc69738f987eaa5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0ukd-9400000000-6ca80e65d20c4cbc9b25 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0200-9620000000-6d48091baa2eae7a7fa1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9200000000-bde656d6bf6a34ee39b8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-3a70f8c5027b4eb6e241 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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 49003 HMDB ID Not Available Pubchem Compound ID 696 Kegg ID C03393 ChemSpider ID 676 Wikipedia ID Not Available BioCyc ID ERYTHRONATE-4P EcoCyc ID ERYTHRONATE-4P Ligand Expo DEZ

Enzymes