Aminoacetone
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 ).
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Structure for HMDB02134 (Aminoacetone)
C3H7NO
73.0938
73.052763851
1-aminopropan-2-one
α-aminoacetone
298-08-8
CC(=O)CN
InChI=1S/C3H7NO/c1-3(5)2-4/h2,4H2,1H3
BCDGQXUMWHRQCB-UHFFFAOYSA-N
This compound belongs to the class of chemical entities 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.
Chemical entities
Organic compounds
Organic oxygen compounds
Organooxygen compounds
Alpha-amino ketones
Aliphatic acyclic compounds
Detected and Quantified
Not Available
Not Available
Solid
Predicted GC-MS Spectrum – GC-MSNot Available
Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-00di-9000000000-11399cdd8e4f4b0b0a0aView in MoNA
Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-05fr-9000000000-a82e70bf32acfda0125fView in MoNA
Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-0a4i-9000000000-b3cd82ec754798e33b8bView in MoNA
Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-00di-9000000000-1c501c72ceda6ba07e56View in MoNA
Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-00di-9000000000-d7cb45a11c770b6c8611View in MoNA
Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-0kml-9000000000-b2494e27f62747d5ed80View in MoNA
Not Available
None
None
Not Available
Not Available
Not Available
Not Available
FDB022860
Not Available
210
C01888
AMINO-ACETONE
38629
1-Amino-2-propanone
HMDB02134
HMDB02134
6502
215
GLM
17906
- 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 ]
Enzymes
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
- Gene Name:
- MAOB
- Uniprot ID:
- P27338
- Molecular weight:
- 58762.475
Reactions
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
- Gene Name:
- MAOA
- Uniprot ID:
- P21397
- Molecular weight:
- 59681.27
Reactions
- General function:
- Lipid transport and metabolism
- Specific function:
- Catalyzes fat and vitamin absorption. Acts in concert with pancreatic lipase and colipase for the complete digestion of dietary triglycerides.
- Gene Name:
- CEL
- Uniprot ID:
- P19835
- Molecular weight:
- 79666.385
- General function:
- Involved in copper ion binding
- Specific function:
- Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
- Gene Name:
- ABP1
- Uniprot ID:
- P19801
- Molecular weight:
- 85377.1
- General function:
- Involved in copper ion binding
- Specific function:
- Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
- Gene Name:
- AOC3
- Uniprot ID:
- Q16853
- Molecular weight:
- 84621.27
Reactions
- General function:
- Involved in copper ion binding
- Specific function:
- Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
- Gene Name:
- AOC2
- Uniprot ID:
- O75106
- Molecular weight:
- 80515.11