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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 | 2017-03-23 04:24:35 UTC |
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Update Date | 2020-06-15 17:04:53 UTC |
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HMDB ID | HMDB0062558 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Pyroglutamine |
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Description | Pyroglutamine (CAS: 2353-44-8), also known as alpha-aminoglutarimide or 3-amino-1,6-dioxopiperidine, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Pyroglutamine is considered to be soluble (in water) and acidic. Pyroglutamine has been identified in the human placenta (PMID: 32033212 ). |
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Structure | |
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Synonyms | Value | Source |
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(3S)-3-Amino-2,6-piperidinedione | HMDB | (3S)-3-Aminohexahydro-2,6-pyridinedione | HMDB | (3S)-3-Aminopiperidine-2,6-dione | HMDB | 3-Amino-2,6-dioxopiperidine | HMDB | 3-Amino-2,6-piperidinedione | HMDB | 3-Aminoglutarimide | HMDB | 3-Aminopiperidine-2,6-dione | HMDB | Glutamic acid imide | HMDB | Glutamimide | HMDB | alpha-Aminoglutarimide | HMDB | α-Aminoglutarimide | HMDB |
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Chemical Formula | C5H8N2O2 |
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Average Molecular Weight | 128.131 |
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Monoisotopic Molecular Weight | 128.058577506 |
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IUPAC Name | (3S)-3-aminopiperidine-2,6-dione |
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Traditional Name | (3S)-3-aminopiperidine-2,6-dione |
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CAS Registry Number | 29883-25-8 |
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SMILES | N[C@H]1CCC(=O)NC1=O |
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InChI Identifier | InChI=1S/C5H8N2O2/c6-3-1-2-4(8)7-5(3)9/h3H,1-2,6H2,(H,7,8,9)/t3-/m0/s1 |
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InChI Key | NPWMTBZSRRLQNJ-VKHMYHEASA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. |
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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 | Alpha amino acids and derivatives |
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Alternative Parents | |
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Substituents | - Alpha-amino acid or derivatives
- Piperidinedione
- 3-aminopiperidine
- Delta-lactam
- Piperidinone
- Piperidine
- Carboxylic acid imide
- Dicarboximide
- Carboxylic acid imide, n-unsubstituted
- Lactam
- Azacycle
- Organoheterocyclic compound
- Organic nitrogen compound
- Organonitrogen compound
- Primary aliphatic amine
- Organooxygen compound
- Primary amine
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organic oxygen compound
- Amine
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Biological location: |
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Physical Properties |
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State | Not Available |
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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 | 259 g/l | ALOGPS | LogP | -1.59 | ALOGPS |
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Predicted Properties | |
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Spectra |
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| Not Available |
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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 | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Attachment loss | | details |
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Associated Disorders and Diseases |
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Disease References | Attachment loss |
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- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
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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 | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | Not Available |
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KEGG Compound ID | Not Available |
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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 | 11984188 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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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 | - 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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