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Record Information |
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Version | 4.0 |
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Status | Detected but not Quantified |
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Creation Date | 2006-05-22 14:17:45 UTC |
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Update Date | 2020-02-26 21:24:00 UTC |
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HMDB ID | HMDB0002273 |
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Secondary Accession Numbers | - HMDB0001344
- HMDB01344
- HMDB02273
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Metabolite Identification |
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Common Name | 4-Hydroxy-L-glutamic acid |
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Description | 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 ). |
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Structure | |
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Synonyms | Value | Source |
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(2S,4R)-2-Amino-4-hydroxypentanedioic acid | ChEBI | L-Erythro-4-hydroxyglutamic acid | ChEBI | (2S,4R)-2-Amino-4-hydroxypentanedioate | Generator | L-Erythro-4-hydroxyglutamate | Generator | Erythro-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-Hydroxy-L-glutamate | HMDB | 4-Hydroxy-L-glutamic acid | HMDB | 4-Hydroxyglutamate | HMDB | 4-Hydroxyglutamic acid | HMDB | erythro-4-Hydroxy-L-glutamic acid | HMDB | (2S)-2-Amino-4-hydroxypentanedioic acid | HMDB | gamma-Hydroxyglutamic acid | HMDB | γ-Hydroxyglutamic acid | HMDB |
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Chemical Formula | C5H9NO5 |
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Average Molecular Weight | 163.1287 |
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Monoisotopic Molecular Weight | 163.048072403 |
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IUPAC Name | (2S,4R)-2-amino-4-hydroxypentanedioic acid |
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Traditional Name | (2S,4R)-2-amino-4-hydroxypentanedioic acid |
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CAS Registry Number | 2485-33-8 |
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SMILES | N[C@@H](C[C@@H](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)/t2-,3+/m0/s1 |
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InChI Key | HBDWQSHEVMSFGY-STHAYSLISA-N |
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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
- 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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Biological location: Source: |
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Process | Naturally occurring process: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00dl-9300000000-192385d58efcfe6d927a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0fr2-1900000000-1952d82430e8d4d017ec | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0g4i-8900000000-9b552b5028c7cac0636c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-006x-9200000000-69e6a42e7b8c893be2b0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-3900000000-a1ac74b59a8487175409 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9600000000-b341efd7d7ac7e6a7652 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-9100000000-a0987d89d6b50b5ee46a | Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022938 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 389696 |
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KEGG Compound ID | C03079 |
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BioCyc ID | L-ERYTHRO-4-HYDROXY-GLUTAMATE |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 440854 |
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PDB ID | Not Available |
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ChEBI ID | 21285 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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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. |
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Material Safety Data Sheet (MSDS) | Not Available |
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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 ]
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