ECMDB: 4-Phospho-D-erythronate (ECMDB20095) (M2MDB000943)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)XML

Proteins (72)

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

MOL SDF PDB SMILES InChI

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

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 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	37.22 m³·mol⁻¹	ChemAxon
Polarizability	15.98 Å³	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:

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

Protein Details

1. Erythronate-4-phosphate dehydrogenase

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.

Protein Details

2. Glyceraldehyde-3-phosphate dehydrogenase A

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.

Protein Details

3. D-erythrose-4-phosphate dehydrogenase

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.

4-Phospho-D-erythronate (ECMDB20095) (M2MDB000943)

Structure for #<Compound:0xacb3cfac>

Enzymes

Reactions

Reactions

Reactions