NP-MRD: Showing NP-Card for 4-phospho-d-erythronic acid (NP0145045)

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Record Information

Version

2.0

Created at

2022-09-02 00:09:11 UTC

Updated at

2022-09-02 00:09:11 UTC

NP-MRD ID

NP0145045

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-phospho-d-erythronic acid

Description

4-Phospho-D-erythronate, also known as 4-phosphoerythronic acid, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. 4-Phospho-D-erythronate is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Phospho-D-erythronate exists in both E. Coli (prokaryote) and yeast (eukaryote). Within yeast, 4-phospho-D-erythronate participates in a number of enzymatic reactions. In particular, 4-phospho-D-erythronate can be biosynthesized from D-erythrose 4-phosphate; which is catalyzed by the enzyme erythrose 4-phosphate dehydrogenase. In addition, 4-phospho-D-erythronate can be converted into 2-oxo-3-hydroxy-4-phosphobutanoic acid; which is mediated by the enzyme erythronate-4-phosphate dehydrogenase. 4-phospho-d-erythronic acid is found in Mus musculus. In yeast, 4-phospho-D-erythronate is involved in the metabolic pathway called the vitamin B6 pathway.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 10211208552D          

 15 14  0  0  0  0            999 V2000
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  2  5  1  6  0  0  0
  3  6  1  1  0  0  0
  7  4  2  0  0  0  0
  8  4  1  0  0  0  0
 12  1  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 13 11  2  0  0  0  0
 13 12  1  0  0  0  0
  2 14  1  6  0  0  0
  3 15  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0145045

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](O)(COP(O)(O)=O)[C@@]([H])(O)C(O)=O

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
ZCZXOHUILRHRQJ-PWNYCUMCSA-N

> <FORMULA>
C4H9O8P

> <MOLECULAR_WEIGHT>
216.0832

> <EXACT_MASS>
216.003503776

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
15.983749664120523

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-2,3-dihydroxy-4-(phosphonooxy)butanoic acid

> <ALOGPS_LOGP>
-2.33

> <JCHEM_LOGP>
-2.2726404579999997

> <ALOGPS_LOGS>
-1.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.469281509972466

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4662169826577083

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6151014494314717

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
37.2189

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-phospho-D-erythronic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-OCT-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   14  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2   12                                                       
CONECT    2    1    3    5   14                                             
CONECT    3    2    4    6   15                                             
CONECT    4    3    7    8                                                  
CONECT    5    2                                                            
CONECT    6    3                                                            
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9   13                                                            
CONECT   10   13                                                            
CONECT   11   13                                                            
CONECT   12    1   13                                                       
CONECT   13    9   10   11   12                                             
CONECT   14    2                                                            
CONECT   15    3                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
4-Phosphoerythronate	ChEBI
4-Phosphoerythronic acid	Generator
4-Phospho-D-erythronic acid	Generator

Chemical Formula

C₄H₉O₈P

Average Mass

216.0832 Da

Monoisotopic Mass

216.00350 Da

IUPAC Name

(2R,3R)-2,3-dihydroxy-4-(phosphonooxy)butanoic acid

Traditional Name

4-phospho-D-erythronic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(COP(O)(O)=O)[C@@]([H])(O)C(O)=O

InChI Identifier

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

InChI Key

ZCZXOHUILRHRQJ-PWNYCUMCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mus musculus	LOTUS Database	35616633

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

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB03108

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C03393

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

49003

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-phospho-d-erythronic acid (NP0145045)

MOL for NP0145045 (4-phospho-d-erythronic acid)

3D MOL for NP0145045 (4-phospho-d-erythronic acid)

3D SDF for NP0145045 (4-phospho-d-erythronic acid)

3D-SDF for NP0145045 (4-phospho-d-erythronic acid)

PDB for NP0145045 (4-phospho-d-erythronic acid)

3D PDB for NP0145045 (4-phospho-d-erythronic acid)

SMILES for NP0145045 (4-phospho-d-erythronic acid)

INCHI for NP0145045 (4-phospho-d-erythronic acid)

Structure for NP0145045 (4-phospho-d-erythronic acid)

3D Structure for NP0145045 (4-phospho-d-erythronic acid)