| Record Information |
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| Version | 4.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2006-05-22 14:17:38 UTC |
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| Update Date | 2019-01-11 19:16:42 UTC |
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| HMDB ID | HMDB0002134 |
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| Secondary Accession Numbers | - HMDB0060177
- HMDB02134
- HMDB60177
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| Metabolite Identification |
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| Common Name | Aminoacetone |
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| Description | Threonine dehydrogenase catalyzes the oxidation of threonine by NAD+ to glycine and acetyl-CoA, but when the ratio acetyl-CoA/CoA increases in nutritional deprivation (e.g., in diabetes) the enzyme produces aminoacetone (Chem. Res. Toxicol., 14 (9), 1323 -1329, 2001). Aminoacetone is thought to be a substrate for SSAO (semicarbazide-sensitive amine oxidase), leading to the production of the toxic product methylglyoxal (Journal of Chromatography B. Volume 824, Issues 1-2 , 25 September 2005, Pages 116-122 ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| 1-amino-2-Propanone | ChEBI | | 1-amino-PROPAN-2-one | ChEBI | | 1-amino-(8CI,9ci)-2-propanone | HMDB | | 1-Aminopropan-2-one | HMDB | | alpha-Aminoacetone | HMDB | | amino-(6CI)-2-propanone | HMDB | | amino-2-Propanone | HMDB | | Ammonioacetone | HMDB |
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| Chemical Formula | C3H7NO |
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| Average Molecular Weight | 73.0938 |
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| Monoisotopic Molecular Weight | 73.052763851 |
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| IUPAC Name | 1-aminopropan-2-one |
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| Traditional Name | α-aminoacetone |
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| CAS Registry Number | 298-08-8 |
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| SMILES | CC(=O)CN |
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| InChI Identifier | InChI=1S/C3H7NO/c1-3(5)2-4/h2,4H2,1H3 |
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| InChI Key | BCDGQXUMWHRQCB-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | This compound belongs to the class of organic compounds known as alpha-amino ketones. These are ketones containing a carboxylic acid, and an amine group attached to the alpha carbon atom relative to C=O group. |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Carbonyl compounds |
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| Direct Parent | Alpha-amino ketones |
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| Alternative Parents | |
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| Substituents | - Alpha-aminoketone
- Organic nitrogen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Primary amine
- Organonitrogen compound
- Primary aliphatic amine
- Amine
- 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 | Route of exposure: 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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| General References | - Dutra F, Knudsen FS, Curi D, Bechara EJ: Aerobic oxidation of aminoacetone, a threonine catabolite: iron catalysis and coupled iron release from ferritin. Chem Res Toxicol. 2001 Sep;14(9):1323-9. [PubMed:11559049 ]
- Karge E, Klinger W: [Effect of the pH value on the dissociation of the aminoketones delta-aminolevulinic acid and aminoacetone by extraction with ether and dichlormethane]. Z Med Lab Diagn. 1981;22(6):358-9. [PubMed:7342529 ]
- Kazachkov M, Yu PH: A novel HPLC procedure for detection and quantification of aminoacetone, a precursor of methylglyoxal, in biological samples. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Sep 25;824(1-2):116-22. [PubMed:16046286 ]
- Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
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