ChemFOnt: Showing chemical card for 4-Hydroxy-L-glutamic acid (CFc000001533)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:11 UTC

Chemfont ID

CFc000001533

Molecule Identification

Common Name

4-Hydroxy-L-glutamic acid

Definition

4-Hydroxy-L-glutamic acid is an intermediate in the metabolism of gamma-hydroxyglutamic acid. Specifically, 4-hydroxy-L-glutamic acid combines with 2-oxoglutarate to produce 4-hydroxy-2-oxoglutarate and glutamate. The reaction can be described as: 4-hydroxy-L-glutamate + 2-oxoglutarate <=> 4-hydroxy-2-oxoglutarate + L-glutamate. This reaction is catalyzed by 4-hydroxyglutamate aminotransferase (PMID: 13948827 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-2-Amino-4-hydroxypentanedioate	ChEBI
(2S)-2-Amino-4-hydroxypentanedioic acid	Generator
4-Hydroxy-L-glutamate	Generator
erythro-4-Hydroxyglutamate	HMDB
L-erythro-4-Hydroxy-glutamate	HMDB
L-erythro-4-Hydroxyglutamate	HMDB

Chemical Formula

C₅H₇NO₅

Average Molecular Weight

161.1128

Monoisotopic Molecular Weight

161.032422339

IUPAC Name

(2S)-2-amino-4-hydroxypentanedioate

Traditional Name

erythro-4-hydroxyglutamate

CAS Registry Number

2485-33-8

SMILES

[H][C@](N)(CC([H])(O)C([O-])=O)C([O-])=O

InChI Identifier

InChI=1S/C5H9NO5/c6-2(4(8)9)1-3(7)5(10)11/h2-3,7H,1,6H2,(H,8,9)(H,10,11)/p-2/t2-,3?/m0/s1

InChI Key

HBDWQSHEVMSFGY-SCQFTWEKSA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
Alpha-amino acid
L-alpha-amino acid
Amino fatty acid
Hydroxy fatty acid
Short-chain hydroxy acid
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
1,3-aminoalcohol
Amino acid
Secondary alcohol
Carboxylic acid
Organic nitrogen compound
Alcohol
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organic oxygen compound
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dicarboxylic acid dianion (CHEBI:16338 )
L-alpha-amino acid anion (CHEBI:16338 )

Functional Ontology

Not Available

Liver (HMDB: HMDB0002273)
Placenta (HMDB: HMDB0002273)

Excreta

Biofluid or Excreta

Feces (PMID: 29808030)

Source

Endogenous

Endogenous (HMDB: HMDB0002273)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Arginine and Proline Metabolism (PathBank: SMP0012004)

Disease pathway

Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency) (PathBank: SMP0120454)
Creatine Deficiency, Guanidinoacetate Methyltransferase Deficiency (PathBank: SMP0120569)
Hyperprolinemia Type I (PathBank: SMP0120719)
Hyperornithinemia with Gyrate Atrophy (HOGA) (PathBank: SMP0120789)
Hyperprolinemia Type II (PathBank: SMP0120501)
Prolinemia Type II (PathBank: SMP0120539)
Prolidase Deficiency (PD) (PathBank: SMP0120541)
L-Arginine:Glycine Amidinotransferase Deficiency (PathBank: SMP0120572)
Hyperornithinemia-Hyperammonemia-Homocitrullinuria [HHH-syndrome] (PathBank: SMP0120790)
Ornithine Aminotransferase Deficiency (OAT Deficiency) (PathBank: SMP0120538)
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency) (PathBank: SMP0120710)
Hyperornithinemia-Hyperammonemia-Homocitrullinuria [HHH-syndrome] (PathBank: SMP0000506)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	565 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-4.2	ChemAxon
logS	0.46	ALOGPS
pKa (Strongest Acidic)	1.68	ChemAxon
pKa (Strongest Basic)	9.16	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	126.51 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	54.41 m³·mol⁻¹	ChemAxon
Polarizability	13.35 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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022938

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5460078

PDB ID

Not Available

ChEBI ID

16338

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Ducrocq, Claire; Decottignies-Le Marechal, Paulette; Azerad, Robert. Synthesis of L-glutamic acid stereospecifically labeled at C-4 with deuterium. Journal of Labelled Compounds and Radiopharmaceuticals (1985), 22(1), 61-70.

Showing chemical card for 4-Hydroxy-L-glutamic acid (CFc000001533)

MOL for CFc000001533 (4-Hydroxy-L-glutamic acid)

3D MOL for CFc000001533 (4-Hydroxy-L-glutamic acid)

3D SDF for CFc000001533 (4-Hydroxy-L-glutamic acid)

3D-SDF for CFc000001533 (4-Hydroxy-L-glutamic acid)

PDB for CFc000001533 (4-Hydroxy-L-glutamic acid)

3D PDB for CFc000001533 (4-Hydroxy-L-glutamic acid)

SMILES for CFc000001533 (4-Hydroxy-L-glutamic acid)

INCHI for CFc000001533 (4-Hydroxy-L-glutamic acid)

Structure for CFc000001533 (4-Hydroxy-L-glutamic acid)

3D Structure for CFc000001533 (4-Hydroxy-L-glutamic acid)