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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

enzymes (4) Show 4 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-05-22 14:17:45 UTC

Update Date

2021-09-14 15:40:00 UTC

HMDB ID

HMDB0002273

Secondary Accession Numbers

HMDB0001344
HMDB01344
HMDB02273

Metabolite Identification

Common Name

4-Hydroxy-L-glutamic acid

Description

4-Hydroxy-L-glutamic acid, also known as erythro-4-hydroxy-L-glutamate or 2-hydroxy-4-aminoglutarate, 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. In humans, 4-hydroxy-L-glutamic acid is involved in the metabolic disorder called the arginine: glycine amidinotransferase deficiency (agat deficiency) pathway. 4-Hydroxy-L-glutamic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 4-Hydroxy-L-glutamic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S,4R)-2-Amino-4-hydroxypentanedioic acid	ChEBI
L-Erythro-4-hydroxyglutamic acid	ChEBI
Erythro-4-hydroxy-L-glutamate	Kegg
(2S,4R)-2-Amino-4-hydroxypentanedioate	Generator
L-Erythro-4-hydroxyglutamate	Generator
Erythro-4-hydroxy-L-glutamic acid	Generator
4-Hydroxy-L-glutamate	Generator
(4R)-4-Hydroxy-L-glutamate	HMDB
(4R)-4-Hydroxy-L-glutamic acid	HMDB
2-Hydroxy-4-aminoglutarate	HMDB
2-Hydroxy-4-aminoglutaric acid	HMDB
4-Hydroxyglutamate	HMDB
4-Hydroxyglutamic acid	HMDB
(2S)-2-Amino-4-hydroxypentanedioic acid	HMDB
gamma-Hydroxyglutamic acid	HMDB
Γ-hydroxyglutamic acid	HMDB
4-Hydroxy-L-glutamic acid	HMDB

Chemical Formula

C₅H₉NO₅

Average Molecular Weight

163.1287

Monoisotopic Molecular Weight

163.048072403

IUPAC Name

(2S,4R)-2-amino-4-hydroxypentanedioic acid

Traditional Name

(2S,4R)-2-amino-4-hydroxypentanedioic acid

CAS Registry Number

2485-33-8

SMILES

N[C@@H](C[C@@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)/t2-,3+/m0/s1

InChI Key

HBDWQSHEVMSFGY-STHAYSLISA-N

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

4-hydroxy-L-glutamic acid (CHEBI:21285 )

Ontology

Disposition

Biological location

Excreta

Feces

Ingestion

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Arginine and proline metabolism

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	565 g/L	ALOGPS
logP	10^(-3.7) g/L	ALOGPS
logP	10^(-4.2) g/L	ChemAxon
logS	10^(-0.34) g/L	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	4	ChemAxon
Polar Surface Area	120.85 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	32.74 m³·mol⁻¹	ChemAxon
Polarizability	14.01 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

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-L-glutamic acid	N[C@@H](C[C@@H](O)C(O)=O)C(O)=O	2373.0	Standard polar	33892256
4-Hydroxy-L-glutamic acid	N[C@@H](C[C@@H](O)C(O)=O)C(O)=O	1300.3	Standard non polar	33892256
4-Hydroxy-L-glutamic acid	N[C@@H](C[C@@H](O)C(O)=O)C(O)=O	1798.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-L-glutamic acid,1TMS,isomer #1	C[Si](C)(C)O[C@H](C[C@H](N)C(=O)O)C(=O)O	1617.9	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](O)C[C@H](N)C(=O)O	1582.5	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,1TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H](N)C[C@@H](O)C(=O)O	1585.4	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,1TMS,isomer #4	C[Si](C)(C)N[C@@H](C[C@@H](O)C(=O)O)C(=O)O	1625.6	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)C[C@@H](O[Si](C)(C)C)C(=O)O	1644.1	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](C[C@H](N)C(=O)O)O[Si](C)(C)C	1632.1	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,2TMS,isomer #3	C[Si](C)(C)N[C@@H](C[C@@H](O[Si](C)(C)C)C(=O)O)C(=O)O	1700.3	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,2TMS,isomer #4	C[Si](C)(C)OC(=O)[C@@H](N)C[C@@H](O)C(=O)O[Si](C)(C)C	1588.2	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,2TMS,isomer #5	C[Si](C)(C)N[C@@H](C[C@@H](O)C(=O)O[Si](C)(C)C)C(=O)O	1679.4	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,2TMS,isomer #6	C[Si](C)(C)N[C@@H](C[C@@H](O)C(=O)O)C(=O)O[Si](C)(C)C	1674.7	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,2TMS,isomer #7	C[Si](C)(C)N([C@@H](C[C@@H](O)C(=O)O)C(=O)O)[Si](C)(C)C	1843.7	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)C[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1662.5	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,3TMS,isomer #2	C[Si](C)(C)N[C@@H](C[C@@H](O[Si](C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C	1732.6	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,3TMS,isomer #3	C[Si](C)(C)N[C@@H](C[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O	1737.2	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,3TMS,isomer #4	C[Si](C)(C)O[C@H](C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	1847.2	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,3TMS,isomer #5	C[Si](C)(C)N[C@@H](C[C@@H](O)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1708.2	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,3TMS,isomer #6	C[Si](C)(C)OC(=O)[C@H](O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1832.5	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,3TMS,isomer #7	C[Si](C)(C)OC(=O)[C@H](C[C@@H](O)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1855.2	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,4TMS,isomer #1	C[Si](C)(C)N[C@@H](C[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1777.1	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,4TMS,isomer #1	C[Si](C)(C)N[C@@H](C[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1803.1	Standard non polar	33892256
4-Hydroxy-L-glutamic acid,4TMS,isomer #1	C[Si](C)(C)N[C@@H](C[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1869.1	Standard polar	33892256
4-Hydroxy-L-glutamic acid,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](C[C@@H](O[Si](C)(C)C)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1878.7	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](C[C@@H](O[Si](C)(C)C)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1882.6	Standard non polar	33892256
4-Hydroxy-L-glutamic acid,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](C[C@@H](O[Si](C)(C)C)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1993.3	Standard polar	33892256
4-Hydroxy-L-glutamic acid,4TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H](C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	1861.0	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,4TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H](C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	1885.0	Standard non polar	33892256
4-Hydroxy-L-glutamic acid,4TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H](C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2012.1	Standard polar	33892256
4-Hydroxy-L-glutamic acid,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](C[C@@H](O)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1874.9	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](C[C@@H](O)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1850.7	Standard non polar	33892256
4-Hydroxy-L-glutamic acid,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](C[C@@H](O)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1947.9	Standard polar	33892256
4-Hydroxy-L-glutamic acid,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](C[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1933.7	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](C[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1919.7	Standard non polar	33892256
4-Hydroxy-L-glutamic acid,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](C[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1856.6	Standard polar	33892256
4-Hydroxy-L-glutamic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H](C[C@H](N)C(=O)O)C(=O)O	1870.5	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)C[C@H](N)C(=O)O	1842.1	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)C[C@@H](O)C(=O)O	1844.9	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](C[C@@H](O)C(=O)O)C(=O)O	1888.6	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2108.4	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](C[C@H](N)C(=O)O)O[Si](C)(C)C(C)(C)C	2100.2	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O	2142.4	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)C[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	2051.2	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N[C@@H](C[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2146.9	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](C[C@@H](O)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2134.5	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N([C@@H](C[C@@H](O)C(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	2275.7	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2303.0	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2381.9	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2383.2	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H](C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2503.0	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N[C@@H](C[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2348.8	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2503.9	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C[C@@H](O)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2511.2	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2590.6	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2538.7	Standard non polar	33892256
4-Hydroxy-L-glutamic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2405.8	Standard polar	33892256
4-Hydroxy-L-glutamic acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2761.0	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2592.3	Standard non polar	33892256
4-Hydroxy-L-glutamic acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2429.2	Standard polar	33892256
4-Hydroxy-L-glutamic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2750.2	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2610.3	Standard non polar	33892256
4-Hydroxy-L-glutamic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2440.7	Standard polar	33892256
4-Hydroxy-L-glutamic acid,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2735.6	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2612.2	Standard non polar	33892256
4-Hydroxy-L-glutamic acid,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2407.3	Standard polar	33892256
4-Hydroxy-L-glutamic acid,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2973.8	Semi standard non polar	33892256
4-Hydroxy-L-glutamic acid,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2803.6	Standard non polar	33892256
4-Hydroxy-L-glutamic acid,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2448.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-L-glutamic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9300000000-192385d58efcfe6d927a	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-L-glutamic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-L-glutamic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-L-glutamic acid 10V, Positive-QTOF	splash10-0fr2-1900000000-1952d82430e8d4d017ec	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-L-glutamic acid 20V, Positive-QTOF	splash10-0g4i-8900000000-9b552b5028c7cac0636c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-L-glutamic acid 40V, Positive-QTOF	splash10-006x-9200000000-69e6a42e7b8c893be2b0	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-L-glutamic acid 10V, Negative-QTOF	splash10-03di-3900000000-a1ac74b59a8487175409	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-L-glutamic acid 20V, Negative-QTOF	splash10-00di-9600000000-b341efd7d7ac7e6a7652	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-L-glutamic acid 40V, Negative-QTOF	splash10-00di-9100000000-a0987d89d6b50b5ee46a	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-L-glutamic acid 10V, Positive-QTOF	splash10-0gi0-3900000000-72a434ff0c346ae54bf5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-L-glutamic acid 20V, Positive-QTOF	splash10-0fk9-9600000000-16a8930ac7a8ed9a8656	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-L-glutamic acid 40V, Positive-QTOF	splash10-00di-9100000000-4825e58f647c6709f63e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-L-glutamic acid 10V, Negative-QTOF	splash10-0006-0900000000-f33be61e6a7e963f5725	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-L-glutamic acid 20V, Negative-QTOF	splash10-0079-9200000000-d4c3022fe2d2d99ba90b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-L-glutamic acid 40V, Negative-QTOF	splash10-0006-9000000000-ce7c939afbade242bd22	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Liver
Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Arginine and proline metabolism	Not Available
Prolidase Deficiency (PD)		Not Available
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)		Not Available
Hyperprolinemia Type II		Not Available
Hyperprolinemia Type I		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022938

KNApSAcK ID

Not Available

Chemspider ID

389696

KEGG Compound ID

C05947

BioCyc ID

L-ERYTHRO-4-HYDROXY-GLUTAMATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440854

PDB ID

Not Available

ChEBI ID

21285

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

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.

Material Safety Data Sheet (MSDS)

Not Available

General References

GOLDSTONE A, ADAMS E: Metabolism of gamma-hydroxyglutamic acid. I. Conversion to alpha-hydroxy-gamma-ketoglutarate by purified glutamic-aspartic transaminase to rat liver. J Biol Chem. 1962 Nov;237:3476-85. [PubMed:13948827 ]
Alaux S, Kusk M, Sagot E, Bolte J, Jensen AA, Brauner-Osborne H, Gefflaut T, Bunch L: Chemoenzymatic synthesis of a series of 4-substituted glutamate analogues and pharmacological characterization at human glutamate transporters subtypes 1-3. J Med Chem. 2005 Dec 15;48(25):7980-92. [PubMed:16335922 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details

1. Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Irreversible conversion of delta-1-pyrroline-5-carboxylate (P5C), derived either from proline or ornithine, to glutamate. This is a necessary step in the pathway interconnecting the urea and tricarboxylic acid cycles. The preferred substrate is glutamic gamma-semialdehyde, other substrates include succinic, glutaric and adipic semialdehydes.
Gene Name:: ALDH4A1
Uniprot ID:: P30038
Molecular weight:: 55117.24

Reactions

Pyrroline hydroxycarboxylic acid + NAD + Water → 4-Hydroxy-L-glutamic acid + NADH + Hydrogen Ion	details
Pyrroline hydroxycarboxylic acid + NADP + Water → 4-Hydroxy-L-glutamic acid + NADPH + Hydrogen Ion	details
4-Hydroxy-L-glutamic acid + NADH + Hydrogen Ion → L-4-Hydroxyglutamate semialdehyde + NAD + Water	details

Enzyme Details

2. Aspartate aminotransferase, cytoplasmic

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Plays a key role in amino acid metabolism (By similarity).
Gene Name:: GOT1
Uniprot ID:: P17174
Molecular weight:: 46247.14

Reactions

4-Hydroxy-L-glutamic acid + Oxoglutaric acid → D-4-Hydroxy-2-oxoglutarate + L-Glutamic acid	details

Enzyme Details

3. Aspartate aminotransferase, mitochondrial

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:: GOT2
Uniprot ID:: P00505
Molecular weight:: 47517.285

Reactions

4-Hydroxy-L-glutamic acid + Oxoglutaric acid → D-4-Hydroxy-2-oxoglutarate + L-Glutamic acid	details

Enzyme Details

4. Proline dehydrogenase 1, mitochondrial

General function:: Involved in proline dehydrogenase activity
Specific function:: Converts proline to delta-1-pyrroline-5-carboxylate.
Gene Name:: PRODH
Uniprot ID:: O43272
Molecular weight:: 56196.675

Reactions

4-Hydroxy-L-glutamic acid + NADH + Hydrogen Ion → L-4-Hydroxyglutamate semialdehyde + NAD + Water	details

Showing metabocard for 4-Hydroxy-L-glutamic acid (HMDB0002273)

MOL for HMDB0002273 (4-Hydroxy-L-glutamic acid)

3D MOL for HMDB0002273 (4-Hydroxy-L-glutamic acid)

3D SDF for HMDB0002273 (4-Hydroxy-L-glutamic acid)

3D-SDF for HMDB0002273 (4-Hydroxy-L-glutamic acid)

PDB for HMDB0002273 (4-Hydroxy-L-glutamic acid)

3D PDB for HMDB0002273 (4-Hydroxy-L-glutamic acid)

SMILES for HMDB0002273 (4-Hydroxy-L-glutamic acid)

INCHI for HMDB0002273 (4-Hydroxy-L-glutamic acid)

Structure for HMDB0002273 (4-Hydroxy-L-glutamic acid)

3D Structure for HMDB0002273 (4-Hydroxy-L-glutamic acid)

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions