Acetyl-N-formyl-5-methoxykynurenamine (BioDeep_00000001283)

 

Secondary id: BioDeep_00001868593

human metabolite Endogenous blood metabolite


代谢物信息卡片


N-[3-[2-(formylamino)-5-methoxyphenyl]-3-oxypropyl]-acetamide

化学式: C13H16N2O4 (264.111)
中文名称: N--乙酰基-N-2-甲酰-5-甲氧基犬尿氨酸
谱图信息: 最多检出来源 Homo sapiens(blood) 11.01%

分子结构信息

SMILES: CC(=O)NCCC(=O)C1=C(C=CC(=C1)OC)NC=O
InChI: InChI=1S/C13H16N2O4/c1-9(17)14-6-5-13(18)11-7-10(19-2)3-4-12(11)15-8-16/h3-4,7-8H,5-6H2,1-2H3,(H,14,17)(H,15,16)

描述信息

Acetyl-N-formyl-5-methoxykynurenamine (AFMK) results from the oxidative cleavage of the pyrrole ring during melatonin oxidation by myeloperoxidase (MPO), a superoxide anion (O)-dependent reaction. AFMK is also expected to be formed from oxidation catalyzed by the unspecific enzyme indoleamine-2,3-dioxygenase (IDO), found in a variety of cell types including monocyte/macrophage lineages. MPO- and IDO-catalyzed melatonin oxidation has the requirement of O in common, a species formed in large amounts in inflammatory conditions. The non-enzymatic formation of AFMK can also be expected by its direct reaction with highly reactive oxygen species, such as hydroxyl radical and singlet oxygen. Thus, we assume that AFMK is a product formed in a route of melatonin metabolism, especially active in inflammation. As AFMK is biologically more active on leukocytes than melatonin, the metabolizing of melatonin to AFMK at inflammatory sites possibly plays a role in immunomodulation. AFMK is found in the CSF of patients with meningitis, and in some samples at a remarkably high concentration, with AFMK found in some patients exceeding the concentration of melatonin normally found in serum. (PMID: 16150112) [HMDB]
Acetyl-N-formyl-5-methoxykynurenamine (AFMK) results from the oxidative cleavage of the pyrrole ring during melatonin oxidation by myeloperoxidase (MPO), a superoxide anion (O)-dependent reaction. AFMK is also expected to be formed from oxidation catalyzed by the unspecific enzyme indoleamine-2,3-dioxygenase (IDO), found in a variety of cell types including monocyte/macrophage lineages. MPO- and IDO-catalyzed melatonin oxidation has the requirement of O in common, a species formed in large amounts in inflammatory conditions. The non-enzymatic formation of AFMK can also be expected by its direct reaction with highly reactive oxygen species, such as hydroxyl radical and singlet oxygen. Thus, we assume that AFMK is a product formed in a route of melatonin metabolism, especially active in inflammation. As AFMK is biologically more active on leukocytes than melatonin, the metabolizing of melatonin to AFMK at inflammatory sites possibly plays a role in immunomodulation. AFMK is found in the CSF of patients with meningitis, and in some samples at a remarkably high concentration. AFMK was also found in some patients to exceed the concentration of melatonin normally found in serum (PMID: 16150112).

同义名列表

11 个代谢物同义名

N-[3-[2-(formylamino)-5-methoxyphenyl]-3-oxypropyl]-acetamide; N-[3-(2-Formamido-5-methoxy-phenyl)-3-oxo-propyl]acetamide; N-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide; N-γ-Acetyl-N-2-formyl-5-methoxykynurenamine; N-Acetyl-N-formyl-5-methoxykynurenamine; N1-Acetyl-N2-formyl-5-methoxykynurenine; Acetyl-N-formyl-5-methoxykynurenamine; Formyl-N-acetyl-5-methoxykynurenamine; NSC 688263; AFMK; K1



数据库引用编号

14 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(3)

PlantCyc(0)

代谢反应

10 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(5)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(5)

PharmGKB(0)

1 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 11 AHR, BCL2, CASP3, CAT, DCX, ELANE, IDO1, NOS2, PTGS1, PTGS2, TYR
Peripheral membrane protein 4 AP1S2, CYP1B1, PTGS1, PTGS2
Endoplasmic reticulum membrane 4 BCL2, CYP1B1, PTGS1, PTGS2
Nucleus 7 AHR, BCL2, CASP3, GABPA, MKI67, MPO, NOS2
cytosol 10 AHR, AP1S2, BCL2, CASP3, CAT, DCX, ELANE, IDO1, NOS2, NQO2
nuclear body 1 MKI67
phagocytic vesicle 1 ELANE
nucleoplasm 7 AHR, CASP3, GABPA, MKI67, MPO, NOS2, NQO2
Cell membrane 1 TNF
Cytoplasmic side 1 AP1S2
cell surface 2 ELANE, TNF
glutamatergic synapse 2 CASP3, DCX
Golgi apparatus 2 AP1S2, PTGS1
Golgi membrane 1 AP1S2
lysosomal membrane 1 AP1S2
neuronal cell body 2 CASP3, TNF
Cytoplasm, cytosol 2 IDO1, NOS2
Lysosome 2 MPO, TYR
plasma membrane 3 IFNLR1, NOS2, TNF
Membrane 5 BCL2, CAT, CYP1B1, IFNLR1, MKI67
caveola 1 PTGS2
extracellular exosome 5 CAT, ELANE, MPO, NQO2, PTGS1
endoplasmic reticulum 2 BCL2, PTGS2
extracellular space 4 CXCL8, ELANE, MPO, TNF
perinuclear region of cytoplasm 2 NOS2, TYR
mitochondrion 3 BCL2, CAT, CYP1B1
protein-containing complex 4 AHR, BCL2, CAT, PTGS2
intracellular membrane-bounded organelle 6 AP1S2, CAT, CYP1B1, MPO, PTGS1, TYR
Microsome membrane 3 CYP1B1, PTGS1, PTGS2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 2 IFNLR1, TYR
Secreted 1 CXCL8
extracellular region 5 CAT, CXCL8, ELANE, MPO, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
mitochondrial matrix 1 CAT
transcription regulator complex 1 AHR
photoreceptor outer segment 1 PTGS1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 TNF
nucleolus 1 MKI67
Melanosome membrane 1 TYR
Cytoplasm, P-body 1 NOS2
P-body 1 NOS2
Early endosome 1 AP1S2
Membrane, clathrin-coated pit 1 AP1S2
clathrin-coated pit 1 AP1S2
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Cytoplasm, perinuclear region 1 NOS2
Membrane raft 1 TNF
pore complex 1 BCL2
focal adhesion 1 CAT
microtubule 1 DCX
Peroxisome 2 CAT, NOS2
Peroxisome matrix 1 CAT
peroxisomal matrix 2 CAT, NOS2
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 1 ELANE
secretory granule 2 ELANE, MPO
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Cell projection, neuron projection 1 DCX
neuron projection 3 DCX, PTGS1, PTGS2
chromatin 2 AHR, GABPA
microtubule associated complex 1 DCX
stereocilium bundle 1 IDO1
phagocytic cup 1 TNF
Chromosome 1 MKI67
cytoskeleton 1 DCX
Nucleus, nucleolus 1 MKI67
Endomembrane system 2 AP1S2, PTGS1
aryl hydrocarbon receptor complex 1 AHR
Cytoplasmic vesicle membrane 1 AP1S2
Melanosome 1 TYR
myelin sheath 1 BCL2
azurophil granule 1 MPO
trans-Golgi network membrane 1 AP1S2
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
endoplasmic reticulum lumen 1 PTGS2
transcription repressor complex 1 ELANE
specific granule lumen 1 ELANE
azurophil granule lumen 2 ELANE, MPO
phagocytic vesicle lumen 1 MPO
death-inducing signaling complex 1 CASP3
AP-type membrane coat adaptor complex 1 AP1S2
membrane coat 1 AP1S2
AP-1 adaptor complex 1 AP1S2
Cytoplasmic vesicle, phagosome 1 ELANE
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
cortical cytoskeleton 1 NOS2
catalase complex 1 CAT
BAD-BCL-2 complex 1 BCL2
smooth muscle contractile fiber 1 IDO1
nuclear aryl hydrocarbon receptor complex 1 AHR
cytosolic aryl hydrocarbon receptor complex 1 AHR
interleukin-28 receptor complex 1 IFNLR1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Liguo Liu, Dongmei Xu, Fengxin Chen, Shengnan Cai, Jin Wei, Jiaheng Deng, Jianhua Zheng, Qi Jin, Wenhui Lun. Identification of potential biomarkers for diagnosis of syphilis from the cerebrospinal fluid based on untargeted metabolomic analysis. Molecular omics. 2023 Apr; ?(?):. doi: 10.1039/d3mo00026e. [PMID: 37185577]
  • Ewa Kulczykowska, Hanna Kalamarz-Kubiak, Magdalena Gozdowska, Ewa Sokołowska. Cortisol and melatonin in the cutaneous stress response system of fish. Comparative biochemistry and physiology. Part A, Molecular & integrative physiology. 2018 04; 218(?):1-7. doi: 10.1016/j.cbpa.2018.01.003. [PMID: 29355753]
  • Guangguo Tan, Haibo Wang, Jianlin Yuan, Weijun Qin, Xin Dong, Hong Wu, Ping Meng. Three serum metabolite signatures for diagnosing low-grade and high-grade bladder cancer. Scientific reports. 2017 04; 7(?):46176. doi: 10.1038/srep46176. [PMID: 28382976]
  • J Jaworek, J Szklarczyk, J Bonior, M Kot, M Goralska, P Pierzchalski, R J Reiter, U Czech, R Tomaszewska. Melatonin metabolite, N(1)-acetyl-N(1)-formyl-5-methoxykynuramine (AFMK), attenuates acute pancreatitis in the rat: in vivo and in vitro studies. Journal of physiology and pharmacology : an official journal of the Polish Physiological Society. 2016 Jun; 67(3):411-21. doi: . [PMID: 27512002]
  • Sida Niu, Feng Li, Dun-Xian Tan, Lirong Zhang, Jeffrey R Idle, Frank J Gonzalez, Xiaochao Ma. Analysis of N1-acetyl-N2-formyl-5-methoxykynuramine/N1-acetyl-5-methoxy-kynuramine formation from melatonin in mice. Journal of pineal research. 2010 Sep; 49(2):106-14. doi: 10.1111/j.1600-079x.2010.00771.x. [PMID: 20545825]
  • Márcio Alberto Geihs, Marcelo Alves Vargas, Fábio Everton Maciel, Sergiane Souza Caldas, Bruno Pinto Cruz, Ednei Gilberto Primel, José Maria Monserrat, Luiz Eduardo Maia Nery. Effect of melatonin in the antioxidant defense system in the locomotor muscles of the estuarine crab Neohelice granulata (Decapoda, Brachyura). General and comparative endocrinology. 2010 Mar; 166(1):72-82. doi: 10.1016/j.ygcen.2009.09.018. [PMID: 19818787]
  • Kailash Manda, Megumi Ueno, Kazunori Anzai. Space radiation-induced inhibition of neurogenesis in the hippocampal dentate gyrus and memory impairment in mice: ameliorative potential of the melatonin metabolite, AFMK. Journal of pineal research. 2008 Nov; 45(4):430-8. doi: 10.1111/j.1600-079x.2008.00611.x. [PMID: 18631288]
  • Natalia Fagali, Angel Catalá. The effect of melatonin and structural analogues on the lipid peroxidation of triglycerides enriched in omega-3 polyunsaturated fatty acids. Life sciences. 2007 Jul; 81(4):299-305. doi: 10.1016/j.lfs.2007.05.013. [PMID: 17603083]
  • Dun-Xian Tan, Lucien C Manchester, Paolo Di Mascio, Glaucia R Martinez, Fernanda M Prado, Russel J Reiter. Novel rhythms of N1-acetyl-N2-formyl-5-methoxykynuramine and its precursor melatonin in water hyacinth: importance for phytoremediation. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2007 Jun; 21(8):1724-9. doi: 10.1096/fj.06-7745com. [PMID: 17314136]
  • Valdecir F Ximenes, João Roberto Fernandes, Vânia B Bueno, Luiz H Catalani, Georgino H de Oliveira, Rosângela G P Machado. The effect of pH on horseradish peroxidase-catalyzed oxidation of melatonin: production of N1-acetyl-N2-5-methoxykynuramine versus radical-mediated degradation. Journal of pineal research. 2007 Apr; 42(3):291-6. doi: 10.1111/j.1600-079x.2007.00419.x. [PMID: 17349028]
  • Kailash Manda, Megumi Ueno, Kazunori Anzai. AFMK, a melatonin metabolite, attenuates X-ray-induced oxidative damage to DNA, proteins and lipids in mice. Journal of pineal research. 2007 Apr; 42(4):386-93. doi: 10.1111/j.1600-079x.2007.00432.x. [PMID: 17439555]
  • Eduardo A Almeida, Clécio F Klitzke, Glaucia R Martinez, Marisa H G Medeiros, Paolo Di Mascio. Synthesis of internal labeled standards of melatonin and its metabolite N1-acetyl-N2-formyl-5-methoxykynuramine for their quantification using an on-line liquid chromatography-electrospray tandem mass spectrometry system. Journal of pineal research. 2004 Jan; 36(1):64-71. doi: 10.1046/j.1600-079x.2003.00098.x. [PMID: 14675132]
  • Stanislav V Rozov, Elena V Filatova, Alexandr A Orlov, Anvara V Volkova, Alexand R A Zhloba, Eduard L Blashko, Nikita V Pozdeyev. N1-acetyl-N2-formyl-5-methoxykynuramine is a product of melatonin oxidation in rats. Journal of pineal research. 2003 Nov; 35(4):245-50. doi: 10.1034/j.1600-079x.2003.00081.x. [PMID: 14521629]
  • Catherine Harthé, Danièle Claudy, Henri Déchaud, Berthe Vivien-Roels, Paul Pévet, Bruno Claustrat. Radioimmunoassay of N-acetyl-N-formyl-5-methoxykynuramine (AFMK): a melatonin oxidative metabolite. Life sciences. 2003 Aug; 73(12):1587-97. doi: 10.1016/s0024-3205(03)00483-1. [PMID: 12865098]
  • Maria R Rodrigues, Dunia Rodriguez, Luiz Henrique Catalani, Momtchilo Russo, Ana Campa. Interferon-gamma independent oxidation of melatonin by macrophages. Journal of pineal research. 2003 Jan; 34(1):69-74. doi: 10.1034/j.1600-079x.2003.02944.x. [PMID: 12485374]
  • D X Tan, L C Manchester, S Burkhardt, R M Sainz, J C Mayo, R Kohen, E Shohami, Y S Huo, R Hardeland, R J Reiter. N1-acetyl-N2-formyl-5-methoxykynuramine, a biogenic amine and melatonin metabolite, functions as a potent antioxidant. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2001 Oct; 15(12):2294-6. doi: 10.1096/fj.01-0309fje. [PMID: 11511530]