| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-05-26 05:43:41 UTC |
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| Update Date | 2016-11-09 01:21:18 UTC |
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| Accession Number | CHEM035394 |
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| Identification |
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| Common Name | 4-Hydroxy-L-glutamic acid |
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| Class | Small Molecule |
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| Description | 4-Hydroxy-L-glutamic acid, also known as 4-hydroxy-L-glutamate or erythro-L-bhga, 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. 4-Hydroxy-L-glutamic acid is possibly soluble (in water) and a very strong basic compound (based on its pKa). 4-Hydroxy-L-glutamic acid exists in all living organisms, ranging from bacteria to humans. 4-Hydroxy-L-glutamic acid participates in a number of enzymatic reactions, within cattle. In particular, 4-Hydroxy-L-glutamic acid can be biosynthesized from pyrroline hydroxycarboxylic acid through the action of the enzyme Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial. In addition, 4-Hydroxy-L-glutamic acid can be converted into L-4-hydroxyglutamate semialdehyde through the action of the enzyme proline dehydrogenase 1, mitochondrial. In cattle, 4-hydroxy-L-glutamic acid is involved in the metabolic pathway called the arginine and proline metabolism pathway. |
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| Contaminant Sources | |
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| Contaminant Type | Not Available |
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| 4-Hydroxy-L-glutamate | Generator | | beta-Hydroxyglutamate | HMDB | | beta-Hydroxyglutamic acid | HMDB | | Erythro-L-bhga | HMDB | | Hydroxyglutamic acid, (DL)-isomer | HMDB | | Hydroxyglutamic acid, erythro-(DL)-isomer | HMDB | | Hydroxyglutamic acid, erythro-(L)-isomer | HMDB | | Hydroxyglutamic acid, sodium salt | HMDB | | Threo-L-bhga | HMDB |
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| Chemical Formula | C5H7NO5 |
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| Average Molecular Mass | 161.113 g/mol |
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| Monoisotopic Mass | 161.032 g/mol |
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| CAS Registry Number | 2485-33-8 |
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| IUPAC Name | 2-amino-4-hydroxypentanedioic acid |
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| Traditional Name | hydroxyglutamic acid |
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| SMILES | N[C@@H](CC(O)C([O-])=O)C([O-])=O |
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| 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 |
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| InChI Key | HBDWQSHEVMSFGY-SCQFTWEKSA-L |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Amino acids, peptides, and analogues |
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| Direct Parent | Glutamic acid and derivatives |
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| Alternative Parents | |
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| Substituents | - Glutamic acid or derivatives
- Alpha-amino acid
- Amino fatty acid
- Hydroxy fatty acid
- Short-chain hydroxy acid
- Alpha-hydroxy acid
- Dicarboxylic acid or derivatives
- Hydroxy acid
- Fatty acid
- Fatty acyl
- 1,3-aminoalcohol
- Secondary alcohol
- Amino acid
- Carboxylic acid
- Primary amine
- Primary aliphatic amine
- Organopnictogen compound
- Alcohol
- Organonitrogen compound
- Carbonyl group
- Organic oxygen compound
- Amine
- Organic oxide
- Organic nitrogen compound
- Organooxygen compound
- Hydrocarbon derivative
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | Not Available |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Not Available |
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| Cellular Locations | Not Available |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Appearance | Not Available |
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| Experimental Properties | | Property | Value |
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| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00kb-0900000000-ce005fc2e4492c63491a | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0g4i-7900000000-c99dab7460465a300d8c | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-006x-9100000000-9ca5dd20ed7c29d06525 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-1900000000-626615b98a6b2fb5e19d | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9800000000-a6e6074af92fb098b762 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-9100000000-68bf4be7fd2ead3fcb1e | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0gi0-3900000000-72a434ff0c346ae54bf5 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0fk9-9600000000-16a8930ac7a8ed9a8656 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00di-9100000000-4825e58f647c6709f63e | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0900000000-f33be61e6a7e963f5725 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0079-9200000000-d4c3022fe2d2d99ba90b | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-ce7c939afbade242bd22 | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | Not Available |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | Not Available |
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| Uses/Sources | Not Available |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB0002273 |
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| FooDB ID | FDB022938 |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | 1447439 |
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| BioCyc ID | L-ERYTHRO-4-HYDROXY-GLUTAMATE |
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| METLIN ID | 6586 |
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| PDB ID | Not Available |
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| Wikipedia Link | Not Available |
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| Chemspider ID | 816 |
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| ChEBI ID | 16338 |
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| PubChem Compound ID | 5460078 |
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| Kegg Compound ID | C03079 |
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| YMDB ID | Not Available |
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| ECMDB ID | ECMDB02273 |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Not Available |
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| General References | | 1. 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. | | 2. 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. | | 3. 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. |
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