ECMDB: 4-Hydroxy-L-threonine (ECMDB20092) (M2MDB000940)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (1)XML

Proteins (491)

Record Information

Version

2.0

Creation Date

2012-05-31 14:27:00 -0600

Update Date

2015-06-03 17:19:17 -0600

Secondary Accession Numbers

ECMDB20092

Identification

Name:

4-Hydroxy-L-threonine

Description

4-hydroxy-L-threonine is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).4-hydroxyl-L-threonine is involved in pyridoxine biosynthesis. This result is consistent with a model in which 4-phospho-hydroxy-L-threonine (synonym, 3-hydroxyhomoserine phosphate), rather than 4-hydroxy-L-threonine, is an obligatory intermediate in pyridoxal 5'-phosphate biosynthesis. (PMID 8595869)

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms:

(2S,3S)-2-amino-3,4-dihydroxybutanoate
(2S,3S)-2-amino-3,4-dihydroxybutanoic acid
2-Amino-3,4-dihydroxy-(S-(R*,R*))-L-Threonate
2-Amino-3,4-dihydroxy-(S-(R*,R*))-L-Threonic acid
3-Hydroxyhomoserine
a-amino-b,g-Dihydroxybutyrate
a-amino-b,g-Dihydroxybutyric acid
Alpha-Amino-beta,gamma-dihydroxybutyrate
Alpha-Amino-beta,gamma-dihydroxybutyric acid
Hydroxythreonine
α-amino-β,γ-Dihydroxybutyrate
α-amino-β,γ-Dihydroxybutyric acid

Chemical Formula:

C₄H₉NO₄

Weight:

Average: 135.1186
Monoisotopic: 135.053157781

InChI Key:

JBNUARFQOCGDRK-GBXIJSLDSA-N

InChI:

InChI=1S/C4H9NO4/c5-3(4(8)9)2(7)1-6/h2-3,6-7H,1,5H2,(H,8,9)/t2-,3+/m1/s1

CAS number:

21768-45-6

IUPAC Name:

(2S,3S)-2-amino-3,4-dihydroxybutanoic acid

Traditional IUPAC Name:

hydroxythreonine

SMILES:

N[C@@H]([C@H](O)CO)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Beta-hydroxy acid
Short-chain hydroxy acid
Hydroxy acid
Fatty acid
1,3-aminoalcohol
1,2-diol
Amino acid
Secondary alcohol
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Primary amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Alcohol
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:28330 )
L-threonine derivative (CHEBI:28330 )
hydroxy-amino acid (CHEBI:28330 )

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	357 g/L	ALOGPS
logP	-3.4	ALOGPS
logP	-4.5	ChemAxon
logS	0.42	ALOGPS
pKa (Strongest Acidic)	1.92	ChemAxon
pKa (Strongest Basic)	8.62	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	103.78 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	28 m³·mol⁻¹	ChemAxon
Polarizability	12.04 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:

Water + O-Phospho-4-hydroxy-L-threonine > 4-Hydroxy-L-threonine + Phosphate
O-Phospho-4-hydroxy-L-threonine + Water <> 4-Hydroxy-L-threonine + Phosphate
4-Hydroxy-L-threonine <> Glycolaldehyde + Glycine
4-Hydroxy-L-threonine + Adenosine triphosphate > Hydrogen ion + O-Phospho-4-hydroxy-L-threonine + ADP

SMPDB Pathways:

Not Available

KEGG Pathways:

Vitamin B6 metabolism ec00750

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ec-9000000000-ed89b9334f5be14dc8c5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-4900000000-dbd9d3d88c247a29f9c9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9100000000-2070d819d44de1960ae0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9100000000-283552f8bd87ff9d06d5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-8900000000-75b8c2945f1960264b7f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pw9-9400000000-43e8a71f87678ae42e12	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-9000000000-437c14b312f426383b44	View 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

Links

External Links:

Resource	Link
CHEBI ID	28330
HMDB ID	Not Available
Pubchem Compound ID	193577
Kegg ID	C06056
ChemSpider ID	167988
Wikipedia ID	Not Available
BioCyc ID	CPD0-2189
EcoCyc ID	CPD0-2189
Ligand Expo	TH6

Enzymes

Protein Details

1. Threonine synthase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the gamma-elimination of phosphate from L- phosphohomoserine and the beta-addition of water to produce L- threonine. To a lesser extent, is able to slowly catalyze the deamination of L-threonine into alpha-ketobutyrate and that of L- serine and 3-chloroalanine into pyruvate. Is also able to rapidly convert vinylglycine to threonine, which proves that the pyridoxal p-quinonoid of vinylglycine is an intermediate in the TS reaction
Gene Name:: thrC
Uniprot ID:: P00934
Molecular weight:: 47113

Reactions

O-phospho-L-homoserine + H(2)O = L-threonine + phosphate.

4-Hydroxy-L-threonine (ECMDB20092) (M2MDB000940)

Structure for #<Compound:0xad647938>

Enzymes

Reactions