Record Information
Version2.0
Creation Date2012-05-31 14:27:12 -0600
Update Date2015-06-03 17:19:18 -0600
Secondary Accession Numbers
  • ECMDB20095
Identification
Name:4-Phospho-D-erythronate
Description4-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
Thumb
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide phosphates
Alternative Parents
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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility19.6 g/LALOGPS
logP-2.3ALOGPS
logP-2.3ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)1.47ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.22 m³·mol⁻¹ChemAxon
Polarizability15.98 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Vitamin B6 1430936196PW000891 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, Positivesplash10-0002-9300000000-6fa3e5b82781cb309499View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-2920000000-a5fad921f0528d94b501View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006w-5900000000-2a302dc69738f987eaa5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ukd-9400000000-6ca80e65d20c4cbc9b25View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0200-9620000000-6d48091baa2eae7a7fa1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-bde656d6bf6a34ee39b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-3a70f8c5027b4eb6e241View 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID49003
HMDB IDNot Available
Pubchem Compound ID696
Kegg IDC03393
ChemSpider ID676
Wikipedia IDNot Available
BioCyc IDERYTHRONATE-4P
EcoCyc IDERYTHRONATE-4P
Ligand ExpoDEZ

Enzymes

General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Catalyzes the oxidation of erythronate-4-phosphate to 3- hydroxy-2-oxo-4-phosphonooxybutanoate
Gene Name:
pdxB
Uniprot ID:
P05459
Molecular weight:
41367
Reactions
4-phospho-D-erythronate + NAD(+) = (3R)-3-hydroxy-2-oxo-4-phosphonooxybutanoate + NADH.
General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, NAD or NADP as acceptor
Specific function:
D-glyceraldehyde 3-phosphate + phosphate + NAD(+) = 3-phospho-D-glyceroyl phosphate + NADH
Gene Name:
gapA
Uniprot ID:
P0A9B2
Molecular weight:
35532
Reactions
D-glyceraldehyde 3-phosphate + phosphate + NAD(+) = 3-phospho-D-glyceroyl phosphate + NADH.
General function:
Involved in erythrose-4-phosphate dehydrogenase activity
Specific function:
Catalyzes the NAD-dependent conversion of D-erythrose 4- phosphate to 4-phosphoerythronate
Gene Name:
epd
Uniprot ID:
P0A9B6
Molecular weight:
37299
Reactions
D-erythrose 4-phosphate + NAD(+) + H(2)O = 4-phosphoerythronate + NADH.