Aminoacetone (BioDeep_00000004787)

 

Secondary id: BioDeep_00001868923

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


1-amino-(8CI,9ci)-2-propanone

化学式: C3H7NO (73.0528)
中文名称: 盐酸乙酰丙酮
谱图信息: 最多检出来源 Homo sapiens(blood) 23.46%

分子结构信息

SMILES: CC(=O)CN
InChI: InChI=1S/C3H7NO/c1-3(5)2-4/h2,4H2,1H3

描述信息

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 ).
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);

同义名列表

10 个代谢物同义名

1-amino-(8CI,9ci)-2-propanone; amino-(6CI)-2-propanone; 1-AMINO-propan-2-one; 1-aminopropan-2-one; 1-Amino-2-propanone; alpha-Aminoacetone; amino-2-Propanone; Ammonioacetone; aminoacetone; Aminoacetone



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(2)

PlantCyc(0)

代谢反应

299 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(3)

WikiPathways(0)

Plant Reactome(269)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(26)

PharmGKB(0)

3 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 9 AOC3, BCL2, CASP3, CAT, FTH1, GLO1, PKM, SDS, XDH
Peripheral membrane protein 2 AOC1, HSD17B6
Endoplasmic reticulum membrane 1 BCL2
Cytoplasmic vesicle, autophagosome 1 FTH1
Nucleus 5 BCL2, CASP3, FTH1, PKM, TDG
autophagosome 1 FTH1
cytosol 10 BCL2, CASP3, CAT, FTH1, GLO1, GSR, MB, PKM, SDS, XDH
nucleoplasm 3 CASP3, GLO1, TDG
Cell membrane 2 AOC1, AOC3
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 1 TPRA1
cell surface 1 AOC3
glutamatergic synapse 1 CASP3
Golgi apparatus 1 AOC3
Golgi membrane 1 INS
lysosomal membrane 1 CP
mitochondrial inner membrane 1 TDH
neuronal cell body 1 CASP3
Lysosome 2 FTH1, IL4I1
acrosomal vesicle 1 IL4I1
plasma membrane 6 AOC1, AOC3, CP, GLO1, TDG, TPRA1
Membrane 5 AOC3, BCL2, CAT, FTH1, TPRA1
extracellular exosome 9 AOC1, CAT, CP, FTH1, GLO1, GSR, MB, PKM, SOD2
Lumenal side 1 HSD17B6
endoplasmic reticulum 3 AOC3, BCL2, HSD17B6
extracellular space 4 AOC1, CP, INS, XDH
bicellular tight junction 1 AOC1
mitochondrion 7 BCL2, CAT, GSR, PKM, SDS, SOD2, TDH
protein-containing complex 2 BCL2, CAT
intracellular membrane-bounded organelle 2 CAT, HSD17B6
Microsome membrane 1 HSD17B6
postsynaptic density 1 CASP3
Secreted 3 CP, IL4I1, INS
extracellular region 7 AOC1, CAT, CP, FTH1, IL4I1, INS, PKM
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
Mitochondrion matrix 1 SOD2
mitochondrial matrix 3 CAT, GSR, SOD2
Extracellular side 1 AOC1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 GSR
Extracellular vesicle 1 PKM
sarcoplasm 1 MB
Early endosome 1 AOC3
Single-pass type II membrane protein 1 AOC3
vesicle 1 PKM
pore complex 1 BCL2
focal adhesion 1 CAT
mitochondrial nucleoid 1 SOD2
Peroxisome 3 AOC1, CAT, XDH
sarcoplasmic reticulum 1 XDH
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
PML body 1 TDG
collagen-containing extracellular matrix 1 PKM
cilium 1 PKM
Secreted, extracellular space 1 AOC1
Cytoplasmic vesicle, secretory vesicle, acrosome 1 IL4I1
blood microparticle 1 CP
sperm midpiece 1 IL4I1
endosome lumen 1 INS
microvillus 1 AOC3
myelin sheath 1 BCL2
ficolin-1-rich granule lumen 3 CAT, FTH1, PKM
secretory granule lumen 3 CAT, INS, PKM
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 CP, INS
specific granule lumen 1 AOC1
tertiary granule lumen 1 FTH1
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
immunological synapse 1 IL4I1
death-inducing signaling complex 1 CASP3
Rough endoplasmic reticulum 1 PKM
Cytoplasm, sarcoplasm 1 MB
Autolysosome 1 FTH1
ferritin complex 1 FTH1
catalase complex 1 CAT
BAD-BCL-2 complex 1 BCL2
[Isoform M2]: Cytoplasm 1 PKM
[Isoform M1]: Cytoplasm 1 PKM


文献列表

  • R D Divine, D Sommer, A Lopez-Hernandez, S A Rankin. Short communication: Evidence for methylglyoxal-mediated browning of Parmesan cheese during low temperature storage. Journal of dairy science. 2012 May; 95(5):2347-54. doi: 10.3168/jds.2011-4828. [PMID: 22541463]
  • Alvaro Arjona-Sánchez, Juan Ruiz-Rabelo, María D Perea, Reyes Vázquez, Adolfo Cruz, María del C Muñoz, Isaac Túnez, Jordi Muntané, Francisco J Padillo. Effects of capecitabine and celecoxib in experimental pancreatic cancer. Pancreatology : official journal of the International Association of Pancreatology (IAP) ... [et al.]. 2010; 10(5):641-7. doi: 10.1159/000288708. [PMID: 21051919]
  • Shengyuan Xiao, Peter H Yu. A fluorometric high-performance liquid chromatography procedure for simultaneous determination of methylamine and aminoacetone in blood and tissues. Analytical biochemistry. 2009 Jan; 384(1):20-6. doi: 10.1016/j.ab.2008.09.029. [PMID: 18845121]
  • Katja Witzel, Annette Weidner, Giridara-Kumar Surabhi, Andreas Börner, Hans-Peter Mock. Salt stress-induced alterations in the root proteome of barley genotypes with contrasting response towards salinity. Journal of experimental botany. 2009; 60(12):3545-57. doi: 10.1093/jxb/erp198. [PMID: 19671579]
  • Adriano Sartori, Humberto M Garay-Malpartida, Maria F Forni, Robert I Schumacher, Fernando Dutra, Mari C Sogayar, Etelvino J H Bechara. Aminoacetone, a putative endogenous source of methylglyoxal, causes oxidative stress and death to insulin-producing RINm5f cells. Chemical research in toxicology. 2008 Sep; 21(9):1841-50. doi: 10.1021/tx8001753. [PMID: 18729331]
  • Chang-Yin Lee, Yi-Chao Hsu, Jir-You Wang, Chien-Chih Chen, Jen-Hwey Chiu. Chemopreventive effect of selenium and Chinese medicinal herbs on N-nitrosobis(2-oxopropyl)amine-induced hepatocellular carcinoma in Syrian hamsters. Liver international : official journal of the International Association for the Study of the Liver. 2008 Jul; 28(6):841-55. doi: 10.1111/j.1478-3231.2008.01698.x. [PMID: 18346132]
  • Michael Kazachkov, Kun Chen, Sergey Babiy, Peter H Yu. Evidence for in vivo scavenging by aminoguanidine of formaldehyde produced via semicarbazide-sensitive amine oxidase-mediated deamination. The Journal of pharmacology and experimental therapeutics. 2007 Sep; 322(3):1201-7. doi: 10.1124/jpet.107.124123. [PMID: 17596537]
  • K Chen, M Kazachkov, P H Yu. Effect of aldehydes derived from oxidative deamination and oxidative stress on beta-amyloid aggregation; pathological implications to Alzheimer's disease. Journal of neural transmission (Vienna, Austria : 1996). 2007; 114(6):835-9. doi: 10.1007/s00702-007-0697-5. [PMID: 17401529]
  • F Boomsma, K F Tipton. Renalase, a catecholamine-metabolising enzyme?. Journal of neural transmission (Vienna, Austria : 1996). 2007; 114(6):775-6. doi: 10.1007/s00702-007-0672-1. [PMID: 17385068]
  • Kun Chen, Jason Maley, Peter H Yu. Potential inplications of endogenous aldehydes in beta-amyloid misfolding, oligomerization and fibrillogenesis. Journal of neurochemistry. 2006 Dec; 99(5):1413-24. doi: 10.1111/j.1471-4159.2006.04181.x. [PMID: 17074066]
  • Toshio Obata. Diabetes and semicarbazide-sensitive amine oxidase (SSAO) activity: a review. Life sciences. 2006 Jun; 79(5):417-22. doi: 10.1016/j.lfs.2006.01.017. [PMID: 16487546]
  • Simrat P Singh, Piero R Gardinali. Trace determination of 1-aminopropanone, a potential marker for wastewater contamination by liquid chromatography and atmospheric pressure chemical ionization-mass spectrometry. Water research. 2006 Feb; 40(3):588-94. doi: 10.1016/j.watres.2005.11.036. [PMID: 16443254]
  • Michael Kazachkov, Peter H Yu. A novel HPLC procedure for detection and quantification of aminoacetone, a precursor of methylglyoxal, in biological samples. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Sep; 824(1-2):116-22. doi: 10.1016/j.jchromb.2005.07.006. [PMID: 16046286]
  • Fernando Dutra, Maria R Ciriolo, Lilia Calabrese, Etelvino J H Bechara. Aminoacetone induces oxidative modification to human plasma ceruloplasmin. Chemical research in toxicology. 2005 Apr; 18(4):755-60. doi: 10.1021/tx049655u. [PMID: 15833036]
  • P Mátyus, B Dajka-Halász, A Földi, N Haider, D Barlocco, K Magyar. Semicarbazide-sensitive amine oxidase: current status and perspectives. Current medicinal chemistry. 2004 May; 11(10):1285-98. doi: 10.2174/0929867043365305. [PMID: 15134520]
  • Peter H Yu, Michael Wang, Hui Fan, Yulin Deng, Diana Gubisne-Haberle. Involvement of SSAO-mediated deamination in adipose glucose transport and weight gain in obese diabetic KKAy mice. American journal of physiology. Endocrinology and metabolism. 2004 Apr; 286(4):E634-41. doi: 10.1152/ajpendo.00272.2003. [PMID: 14656718]
  • Hiroyasu Kinemuchi, Haruyo Sugimoto, Toshio Obata, Nobunori Satoh, Shiro Ueda. Selective inhibitors of membrane-bound semicarbazide-sensitive amine oxidase (SSAO) activity in mammalian tissues. Neurotoxicology. 2004 Jan; 25(1-2):325-35. doi: 10.1016/s0161-813x(03)00118-9. [PMID: 14697907]
  • Jeff O'Sullivan, Mercedes Unzeta, Joe Healy, Michael I O'Sullivan, Gavin Davey, Keith F Tipton. Semicarbazide-sensitive amine oxidases: enzymes with quite a lot to do. Neurotoxicology. 2004 Jan; 25(1-2):303-15. doi: 10.1016/s0161-813x(03)00117-7. [PMID: 14697905]
  • Peter H Yu, Shannon Wright, Ellen H Fan, Zhao-Rong Lun, Diana Gubisne-Harberle. Physiological and pathological implications of semicarbazide-sensitive amine oxidase. Biochimica et biophysica acta. 2003 Apr; 1647(1-2):193-9. doi: 10.1016/s1570-9639(03)00101-8. [PMID: 12686132]
  • P H Yu, M Wang, Y L Deng, H Fan, L Shira-Bock. Involvement of semicarbazide-sensitive amine oxidase-mediated deamination in atherogenesis in KKAy diabetic mice fed with high cholesterol diet. Diabetologia. 2002 Sep; 45(9):1255-62. doi: 10.1007/s00125-002-0903-9. [PMID: 12242458]
  • Alasdair J Edgar. Molecular cloning and tissue distribution of mammalian L-threonine 3-dehydrogenases. BMC biochemistry. 2002 Jun; 3(?):19. doi: 10.1186/1471-2091-3-19. [PMID: 12097150]
  • M Dawit, I D Williams, M F Fitzsimons. Determination of 1-aminopropan-2-one, a dissolved sewage component, in water samples. Water research. 2001 Apr; 35(5):1135-40. doi: 10.1016/s0043-1354(00)00371-7. [PMID: 11268833]
  • P H Yu, B A Davis, Y Deng. 2-Bromoethylamine as a potent selective suicide inhibitor for semicarbazide-sensitive amine oxidase. Biochemical pharmacology. 2001 Mar; 61(6):741-8. doi: 10.1016/s0006-2952(01)00524-x. [PMID: 11266660]
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