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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2019-01-11 19:15:12 UTC |
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HMDB ID | HMDB0000854 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Formiminoglutamic acid |
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Description | Measurement of this acid in the urine after oral administration of histidine provides the basis for the diagnostic test of folic acid deficiency and of megaloblastic anemia of pregnancy. |
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Structure | |
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Synonyms | Value | Source |
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N-Formimidoyl-L-glutamate | ChEBI | N-formimino-L-Glutamate | ChEBI | N-Formimidoyl-L-glutamic acid | Generator | Formiminoglutamate | Generator | N-formimino-L-Glutamic acid | Generator | formimino-Glu | HMDB | formimino-L-Glutamate | HMDB | formimino-L-Glutamic acid | HMDB | N-(Iminomethyl)-L-glutamic acid | HMDB | N-Formimidoyl-glutamic acid | HMDB | N-formimino-Glutamate | HMDB | Acid, formiminoglutamic | MeSH | FIGLU | MeSH |
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Chemical Formula | C6H10N2O4 |
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Average Molecular Weight | 174.1546 |
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Monoisotopic Molecular Weight | 174.064056818 |
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IUPAC Name | (2S)-2-methanimidamidopentanedioic acid |
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Traditional Name | N-formimino-L-glutamate |
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CAS Registry Number | 816-90-0 |
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SMILES | OC(=O)CC[C@H](NC=N)C(O)=O |
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InChI Identifier | InChI=1S/C6H10N2O4/c7-3-8-4(6(11)12)1-2-5(9)10/h3-4H,1-2H2,(H2,7,8)(H,9,10)(H,11,12)/t4-/m0/s1 |
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InChI Key | NRXIKWMTVXPVEF-BYPYZUCNSA-N |
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Chemical Taxonomy |
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Description | This compound belongs to the class of organic compounds known as glutamic acid and derivatives. These 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
- Dicarboxylic acid or derivatives
- Fatty acid
- Amidine
- Carboxylic acid amidine
- Carboxylic acid
- Carboximidamide
- Propargyl-type 1,3-dipolar organic compound
- Organic 1,3-dipolar compound
- Formamidine
- Organooxygen compound
- Carbonyl group
- Organic nitrogen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Organic oxide
- Organopnictogen compound
- 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 | Source: Biological location: |
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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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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 13.400-21.800 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.47 (0.0-0.80) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | - Geigy Scientific ...
- West Cadwell, N.J...
- Basel, Switzerlan...
| details | Urine | Detected and Quantified | 0.90 +/- 0.71 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal Cancer | | details | Urine | Detected and Quantified | 780.114-1876.796 umol/mmol creatinine | Children (1-13 years old) | Both | Glutamate formiminotransferase deficiency | | details |
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Associated Disorders and Diseases |
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Disease References | Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
| Glutamate formiminotransferase deficiency |
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- Perry TL, Applegarth DA, Evans ME, Hansen S, Jellum E: Metabolic studies of a family with massive formiminoglutamic aciduria. Pediatr Res. 1975 Mar;9(3):117-22. [PubMed:235753 ]
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Associated OMIM IDs | - 114500 (Colorectal cancer)
- 229100 (Glutamate formiminotransferase deficiency)
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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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FoodDB ID | FDB022280 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 388370 |
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KEGG Compound ID | C00439 |
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BioCyc ID | N-FORMIMINO-L-GLUTAMATE |
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BiGG ID | 34986 |
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Wikipedia Link | Formiminoglutamic acid |
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METLIN ID | 5817 |
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PubChem Compound | 439233 |
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PDB ID | NIG |
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ChEBI ID | 7274 |
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References |
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Synthesis Reference | Tabor, Herbert; Rabinowitz, Jesse C. Insts. Formiminoglycine, formimino-L-aspartic acid, and formimino-L-glutamic acid. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Hilton JF, Christensen KE, Watkins D, Raby BA, Renaud Y, de la Luna S, Estivill X, MacKenzie RE, Hudson TJ, Rosenblatt DS: The molecular basis of glutamate formiminotransferase deficiency. Hum Mutat. 2003 Jul;22(1):67-73. [PubMed:12815595 ]
- Haurani FI, Hall CA, Rubin R: Megaloblastic anemia as a result of an abnormal transcobalamin II (Cardeza). J Clin Invest. 1979 Nov;64(5):1253-9. [PubMed:500809 ]
- Perry TL, Applegarth DA, Evans ME, Hansen S, Jellum E: Metabolic studies of a family with massive formiminoglutamic aciduria. Pediatr Res. 1975 Mar;9(3):117-22. [PubMed:235753 ]
- Verhoeven NM, Wanders RJ, Poll-The BT, Saudubray JM, Jakobs C: The metabolism of phytanic acid and pristanic acid in man: a review. J Inherit Metab Dis. 1998 Oct;21(7):697-728. [PubMed:9819701 ]
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