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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 | 2009-03-03 11:17:37 UTC |
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Update Date | 2020-02-26 21:35:45 UTC |
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HMDB ID | HMDB0011738 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | N2-gamma-Glutamylglutamine |
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Description | N2-gamma-Glutamylglutamine, also known as gamma-L-Glu-L-Gln or L-gamma-glutamyl-L-glutamine, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. N2-gamma-Glutamylglutamine is a very strong basic compound (based on its pKa). N2-gamma-Glutamylglutamine is a dipeptide obtained from the condensation of the gamma-carboxy group of glutamic acid with the alpha-amino group of glutamine. Some dipeptides are known to have physiological or cell-signalling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. |
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Structure | |
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Synonyms | Value | Source |
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γ-Glu-Gln | HMDB, Generator | γ-L-Glu-L-Gln | HMDB, Generator | γ-Glutamylglutamine | HMDB, Generator | γ-L-Glutamyl-L-glutamine | HMDB | L-γ-Glutamyl-L-glutamine | HMDB | N2-γ-Glutamylglutamine | HMDB, Generator | N2-L-γ-Glutamylglutamine | HMDB | N2-L-γ-Glutamyl-L-glutamine | HMDB | gamma-Glu-Gln | HMDB, MeSH | gamma-L-Glu-L-Gln | HMDB, ChEBI | gamma-Glutamylglutamine | HMDB | gamma-L-Glutamyl-L-glutamine | HMDB | L-gamma-Glutamyl-L-glutamine | HMDB | N2-L-gamma-Glutamylglutamine | HMDB | N2-L-gamma-Glutamyl-L-glutamine | HMDB | N2-gamma-Glutamylglutamine | HMDB | g-L-Glu-L-Gln | Generator | g-Glutamyl glutamine | Generator, HMDB | γ-glutamyl glutamine | Generator, HMDB | g-Glu-Gln | Generator | N2-g-Glutamylglutamine | Generator | g-Glutamylglutamine | Generator |
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Chemical Formula | C10H17N3O6 |
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Average Molecular Weight | 275.2585 |
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Monoisotopic Molecular Weight | 275.111735291 |
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IUPAC Name | (2S)-2-[(4S)-4-amino-4-carboxybutanamido]-4-carbamoylbutanoic acid |
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Traditional Name | (2S)-2-[(4S)-4-amino-4-carboxybutanamido]-4-carbamoylbutanoic acid |
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CAS Registry Number | 10148-81-9 |
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SMILES | N[C@@H](CCC(=O)N[C@@H](CCC(N)=O)C(O)=O)C(O)=O |
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InChI Identifier | InChI=1S/C10H17N3O6/c11-5(9(16)17)1-4-8(15)13-6(10(18)19)2-3-7(12)14/h5-6H,1-4,11H2,(H2,12,14)(H,13,15)(H,16,17)(H,18,19)/t5-,6-/m0/s1 |
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InChI Key | JBFYFLXEJFQWMU-WDSKDSINSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. |
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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 | Dipeptides |
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Alternative Parents | |
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Substituents | - Alpha-dipeptide
- Gamma-glutamyl alpha-amino acid
- Glutamine or derivatives
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- N-acyl-l-alpha-amino acid
- N-acyl-l-glutamine
- Alpha-amino acid
- Alpha-amino acid or derivatives
- L-alpha-amino acid
- N-acyl-amine
- Fatty acyl
- Fatty acid
- Dicarboxylic acid or derivatives
- Fatty amide
- Secondary carboxylic acid amide
- Primary carboxylic acid amide
- Amino acid or derivatives
- Carboxamide group
- Amino acid
- Carboxylic acid
- Organic nitrogen compound
- Primary aliphatic amine
- Organonitrogen compound
- Organooxygen compound
- Primary amine
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organopnictogen compound
- Amine
- Organic oxygen 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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Physiological effect | Health effect: |
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Disposition | Source: Biological location: |
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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 | splash10-001l-9560000000-a956f772592da08ac91b | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-00dl-9314100000-7288034a17d80463b7ca | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , positive | splash10-0002-0900000000-aa0c06e268e954c25179 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a59-0290000000-53ebbfe26a1610c7d206 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01q9-1790000000-8b9c77dbe3ee9bfa3360 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a59-9600000000-7cf2074b159a06a79e69 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-05fr-0090000000-1e9b60fa2e6418acc332 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0bvm-3590000000-ebbac377891f30e322da | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9300000000-3685d99d954b21693f1c | Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Cerebrospinal Fluid (CSF) | Detected and Quantified | 2.46 +/- 0.47 uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 117.00 (20.00-214.00) uM | Adult (>18 years old) | Both | Hyperammonemia | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 2.07 +/- 0.52 uM | Adult (>18 years old) | Both | Schizophrenia | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 258.00 uM | Adult (>18 years old) | Both | Hyperammonemia | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Crohns disease | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Iron deficiency | | details |
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Associated Disorders and Diseases |
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Disease References | Hyperammonemia |
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- Hammond JW, Potter M, Truscott R, Wilcken B: gamma-Glutamylglutamine identified in plasma and cerebrospinal fluid from hyperammonaemic patients. Clin Chim Acta. 1990 Dec 24;194(2-3):173-83. [PubMed:2093471 ]
| Schizophrenia |
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- Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. [PubMed:7595563 ]
| Crohn's disease |
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- Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
| Iron deficiency |
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- Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
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Associated OMIM IDs | |
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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 | FDB028416 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 133013 |
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KEGG Compound ID | C05283 |
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BioCyc ID | Not Available |
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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 | 150914 |
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PDB ID | Not Available |
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ChEBI ID | 73707 |
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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 | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- 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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