P. aeruginosa Metabolome Database: Aminoacetone (PAMDB000441)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000441

Identification

Name:

Aminoacetone

Description:

Threonine dehydrogenase catalyzes the oxidation of threonine by NAD+ to glycine and acetyl-CoA (5), but when the ratio acetyl-CoA/CoA increases in nutritional deprivation (e.g., in diabetes) the enzyme produces AA. (Chem. Res. Toxicol., 14 (9), 1323 -1329, 2001);

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

1-Amino-(8CI,9CI)-2-propanone
1-Amino-2-propanone
1-Aminopropan-2-one
a-Aminoacetone
Alpha-Aminoacetone
Amino-(6CI)-2-propanone
Amino-2-propanone
α-Aminoacetone

Chemical Formula:

C₃H₇NO

Average Molecular Weight:

73.0938

Monoisotopic Molecular Weight:

73.052763851

InChI Key:

BCDGQXUMWHRQCB-UHFFFAOYSA-N

InChI:

InChI=1S/C3H7NO/c1-3(5)2-4/h2,4H2,1H3

CAS number:

298-08-8

IUPAC Name:

1-aminopropan-2-one

Traditional IUPAC Name:

α-aminoacetone

SMILES:

CC(=O)CN

Chemical Taxonomy

Taxonomy 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.

Kingdom

Organic compounds

Super Class

Organooxygen compounds

Class

Carbonyl compounds

Sub Class

Ketones

Direct Parent

Alpha-amino ketones

Alternative Parents

Substituents

Alpha-aminoketone
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Primary aliphatic amine
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

propanone (CHEBI:17906 )

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	528.0 mg/mL	ALOGPS
logP	-1.3	ALOGPS
logP	-0.82	ChemAxon
logS	0.86	ALOGPS
pKa (Strongest Acidic)	17.3	ChemAxon
pKa (Strongest Basic)	7.84	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.09 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	19.55 m³·mol^-1	ChemAxon
Polarizability	7.71 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Aminoacetone + Hydrogen ion + NADH <> 1-Amino-2-propanol + NAD
L-2-Amino-3-oxobutanoic acid + Hydrogen ion > Aminoacetone + Carbon dioxide
Aminoacetone + Water + Oxygen <> Pyruvaldehyde + Ammonia + Hydrogen peroxide
Aminoacetone + Water + Oxygen > Hydrogen ion + Pyruvaldehyde + Ammonia + Hydrogen peroxide
L-Allothreonine + NADP + L-2-Amino-3-oxobutanoic acid <> Aminoacetone + Carbon dioxide + NADPH + Hydrogen ion
1-Amino-2-propanol + NAD + 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene < NADH + Hydrogen ion + Aminoacetone

Pathways:

Glycine, serine and threonine metabolism pae00260
Pyrimidine metabolism pae00240

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-11399cdd8e4f4b0b0a0a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-9000000000-a82e70bf32acfda0125f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-b3cd82ec754798e33b8b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-1c501c72ceda6ba07e56	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-d7cb45a11c770b6c8611	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kml-9000000000-b2494e27f62747d5ed80	View in MoNA

References

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
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
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
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
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 Mar 3. doi: 10.1038/nbt.2488. Pubmed: 23455439
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Turner, J. M. Aminoacetone production by microorganisms. Biochemical Journal (1966), 98(1), 7P.

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17906
HMDB ID	HMDB02134
Pubchem Compound ID	215
Kegg ID	C01888
ChemSpider ID	210
Wikipedia	1-Amino-2-propanone
BioCyc ID	AMINO-ACETONE
EcoCyc ID	AMINO-ACETONE
Ligand Expo	GLM

Aminoacetone (PAMDB000441)

Structure for Aminoacetone (PAMDB000441)