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Human Metabolome Database Version 2.5

 

Showing metabocard for Acetyl-N-formyl-5-methoxykynurenamine (HMDB04259)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-08-13 16:27:56
Update Date 2009-05-26 17:10:52
Accession Number HMDB04259
Secondary Accession Numbers Not Available
Common Name Acetyl-N-formyl-5-methoxykynurenamine
Description 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)
Synonyms
  1. N-Acetyl-N-formyl-5-methoxykynurenamine
  2. AFMK
  3. Formyl-N-acetyl-5-methoxykynurenamine
  4. N-[3-(2-formamido-5-methoxy-phenyl)-3-oxo-propyl]acetamide
Chemical IUPAC Name N-[3-(2-formamido-5-methoxy-phenyl)-3-oxo-propyl]acetamide
Chemical Formula C13H16N2O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
—
Class
  • Amino Ketones
Sub Class
—
Family
  • Mammalian Metabolite
Species
  • ketone
  • alkyl aryl ether
  • secondary carboxylic acid amide
  • aromatic compound
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 264.277
Monoisotopic Molecular Weight 264.110992
Isomeric SMILES COC1=CC(C(=O)CCNC(C)=O)=C(NC=O)C=C1
Canonical SMILES COC1=CC(C(=O)CCNC(C)=O)=C(NC=O)C=C1
KEGG Compound ID C05642 Link Image
BioCyc ID Not Available
BiGG ID 46183 Link Image
Wikipedia Link Not Available
NuGOwiki Link HMDB04259 Link Image
Metagene Link HMDB04259 Link Image
METLIN ID Not Available
PubChem Compound 171161 Link Image
PubChem Substance 7953 Link Image
ChEBI ID Not Available
CAS Registry Number 52450-38-1
InChI Identifier InChI=1/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)
Synthesis Reference de Almeida Eduardo A; Martinez Glaucia R; Klitzke Clecio F; de Medeiros Marisa H G; Di Mascio Paolo Oxidation of melatonin by singlet molecular oxygen (O2(1deltag)) produces N1-acetyl-N2-formyl-5-methoxykynurenine. Journal of pineal research (2003), 35(2), 131-7.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.169 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity -0.158 Source: PhysProp
Predicted LogP/Hydrophobicity 0.50 [Predicted by ALOGPS]; 0.6 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location
  • Blood
  • Cerebrospinal Fluid
Tissue Location Not Available
Concentrations (Normal)
Biofluid Blood
Value 0.000065 (0.000059-0.00189) uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Harthe C, Claudy D, Dechaud H, Vivien-Roels B, Pevet P, Claustrat B: Radioimmunoassay of N-acetyl-N-formyl-5-methoxykynuramine (AFMK): a melatonin oxidative metabolite. Life Sci. 2003 Aug 8;73(12):1587-97. [PubMed Link Image]
Biofluid CSF
Value 0 uM
Age Adult:>18 yrs old
Sex N/A
Patient information Normal
Comments Not Available
References
  • Silva SO, Ximenes VF, Livramento JA, Catalani LH, Campa A: High concentrations of the melatonin metabolite, N1-acetyl-N2-formyl-5-methoxykynuramine, in cerebrospinal fluid of patients with meningitis: a possible immunomodulatory mechanism. J Pineal Res. 2005 Oct;39(3):302-6. [PubMed Link Image]
Concentrations (Abnormal)
Biofluid CSF
Value 0.28 (0.06-0.50) uM
Age Adult:>18 yrs old
Sex N/A
Condition Meningitis
Comments Viral
References
  • Silva SO, Ximenes VF, Livramento JA, Catalani LH, Campa A: High concentrations of the melatonin metabolite, N1-acetyl-N2-formyl-5-methoxykynuramine, in cerebrospinal fluid of patients with meningitis: a possible immunomodulatory mechanism. J Pineal Res. 2005 Oct;39(3):302-6. [PubMed Link Image]
Associated Disorders
Condition References
Meningitis
  • Silva SO, Ximenes VF, Livramento JA, Catalani LH, Campa A: High concentrations of the melatonin metabolite, N1-acetyl-N2-formyl-5-methoxykynuramine, in cerebrospinal fluid of patients with meningitis: a possible immunomodulatory mechanism. J Pineal Res. 2005 Oct;39(3):302-6. [PubMed Link Image]
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Tryptophan Metabolism SMP00063 Link Image map00380 Link Image
General References
  1. Silva SO, Ximenes VF, Livramento JA, Catalani LH, Campa A: High concentrations of the melatonin metabolite, N1-acetyl-N2-formyl-5-methoxykynuramine, in cerebrospinal fluid of patients with meningitis: a possible immunomodulatory mechanism. J Pineal Res. 2005 Oct;39(3):302-6. [PubMed Link Image]
Metabolic Enzymes
  1. Indoleamine 2,3-dioxygenase-like protein 1
Enzyme 1 [top]
Enzyme 1 ID 13115
Enzyme 1 Name Indoleamine 2,3-dioxygenase-like protein 1
Enzyme 1 Synonyms
  1. Indoleamine-pyrrole 2,3-dioxygenase-like protein 1
Enzyme 1 Gene Name INDOL1
Enzyme 1 Protein Sequence >Indoleamine 2,3-dioxygenase-like protein 1 
MEPHRPNVKTAVPLSLESYHISEEYGFLLPDSLKELPDHYRPWMEIANKLPQLIDAHQLQ
AHVDKMPLLSCQFLKGHREQRLAHLVLSFLTMGYVWQEGEAQPAEVLPRNLALPFVEVSR
NLGLPPILVHSDLVLTNWTKKDPDGNLETIISFPGGESLHGFILVTALVEKEAVPGIKAL
VQATNAILQPNQEALLQALQRLRLSIQDITKTLGQMHDYVDPDIFYAGIRIFLSGWKDNP
AMPAGLMYEGVSQEPLKYSGGSAAQSTVLHAFDEFLGIRHSKESGDFLYRMRDYMPPSHK
AFIEDIHSAPSLRDYILSSGQDHLLTAYNQCVQALAELRSYHITMVTKYLITAAAKAKHG
KPNHLPGPPQALKDRGTGGTAVMSFLKSVRDKTLESILHPRG
Enzyme 1 Number of Residues 402
Enzyme 1 Molecular Weight 44865
Enzyme 1 Theoretical pI 6.94
Enzyme 1 GO Classification
Function
  • binding
  • heme binding
  • tetrapyrrole binding
Process
—
Component
—
Enzyme 1 General Function Not Available
Enzyme 1 Specific Function Not Available
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 34536196 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q6ZQW0 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name I23OL_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence Not Available
Enzyme 1 GenBank Gene ID AK128691 Link Image
Enzyme 1 GeneCard ID Q6ZQW0 Link Image
Enzyme 1 GenAtlas ID INDOL1 Link Image
Enzyme 1 HGNC ID HGNC:27269 Link Image
Enzyme 1 Chromosome Location Not Available
Enzyme 1 Locus Not Available
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References Not Available
Enzyme 1 Metabolite References Not Available