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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 15:27:56 UTC

Update Date

2020-02-26 21:25:05 UTC

HMDB ID

HMDB0004259

Secondary Accession Numbers

HMDB04259

Metabolite Identification

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. AFMK was also found in some patients to exceed the concentration of melatonin normally found in serum (PMID: 16150112 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0004259
     RDKit          3D
Acetyl-N-formyl-5-methoxykynurenamine
 35 35  0  0  0  0  0  0  0  0999 V2000
    3.1346   -2.4755    2.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9015   -1.9647    1.7791 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8968   -0.7160    1.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0491   -0.0021    0.9714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0490    1.2424    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8633    1.7883   -0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8870    3.0791   -0.6601 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0411    3.7632   -1.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2291    3.4349   -1.0102 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6841    1.0582    0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5905    1.5190   -0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454    2.5754   -1.0525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8586    0.7732   -0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1277   -0.2399   -1.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3485   -0.9702   -1.0092 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5893   -1.7582    0.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8654   -2.4820    0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7199   -1.8524    1.0183 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036   -0.1909    0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8741   -2.5691    1.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0300   -3.4498    2.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361   -1.7572    2.9695 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0215   -0.3872    1.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9784    1.7676    0.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9518    3.5708   -0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8802    4.7844   -1.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8433    0.3062    0.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7358    1.4859   -0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1052    0.2561   -2.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070   -0.9838   -1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0878   -0.8873   -1.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6290   -3.5046    0.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5071   -2.0265    1.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4266   -2.4679   -0.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2243   -0.7194    0.8389 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  6 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 10 19  2  0
 19  3  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 19 35  1  0
M  END


  Mrv1652301231818222D          

 19 19  0  0  0  0            999 V2000
10000.839710002.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.553610001.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.266010002.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.980410001.5993    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.692810002.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.405110001.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.692810002.8368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.839710002.8368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.415510002.8368    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.702310003.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.989110002.8368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.4155 9999.5426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6982 9999.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.128710001.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.414210002.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.699510001.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.699510000.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.414110000.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.128810000.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 13  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 14  1  0  0  0  0
 18 12  1  0  0  0  0
 15  9  1  0  0  0  0
  1 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004259

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(C(=O)CCNC(C)=O)=C(NC=O)C=C1

> <INCHI_IDENTIFIER>
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)

> <INCHI_KEY>
JYWNYMJKURVPFH-UHFFFAOYSA-N

> <FORMULA>
C13H16N2O4

> <MOLECULAR_WEIGHT>
264.2771

> <EXACT_MASS>
264.11100701

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.128527652920056

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide

> <ALOGPS_LOGP>
0.50

> <JCHEM_LOGP>
0.34396322500000004

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.91444802762295

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.901185222069476

> <JCHEM_PKA_STRONGEST_BASIC>
-1.571848798118829

> <JCHEM_POLAR_SURFACE_AREA>
84.5

> <JCHEM_REFRACTIVITY>
70.79940000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004259
     RDKit          3D
Acetyl-N-formyl-5-methoxykynurenamine
 35 35  0  0  0  0  0  0  0  0999 V2000
    3.1346   -2.4755    2.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9015   -1.9647    1.7791 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8968   -0.7160    1.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0491   -0.0021    0.9714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0490    1.2424    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8633    1.7883   -0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8870    3.0791   -0.6601 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0411    3.7632   -1.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2291    3.4349   -1.0102 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6841    1.0582    0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5905    1.5190   -0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454    2.5754   -1.0525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8586    0.7732   -0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1277   -0.2399   -1.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3485   -0.9702   -1.0092 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5893   -1.7582    0.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8654   -2.4820    0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7199   -1.8524    1.0183 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036   -0.1909    0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8741   -2.5691    1.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0300   -3.4498    2.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361   -1.7572    2.9695 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0215   -0.3872    1.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9784    1.7676    0.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9518    3.5708   -0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8802    4.7844   -1.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8433    0.3062    0.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7358    1.4859   -0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1052    0.2561   -2.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070   -0.9838   -1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0878   -0.8873   -1.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6290   -3.5046    0.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5071   -2.0265    1.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4266   -2.4679   -0.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2243   -0.7194    0.8389 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  6 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 10 19  2  0
 19  3  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 19 35  1  0
M  END

HEADER    PROTEIN                                 23-JAN-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JAN-18         0                                  
HETATM    1  C   UNK     0    8668.2348670.425   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.5678669.652   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8670.8978670.425   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0    8672.2308669.652   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0    8673.5608670.425   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8674.8898669.652   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8673.5608671.962   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8668.2348671.962   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0    8665.5768671.962   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0    8664.2448672.727   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8662.9138671.962   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8665.5768665.813   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8664.2378665.038   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8666.9078669.655   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.5738670.426   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.2398669.655   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8664.2398668.115   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8665.5738667.345   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.9078668.115   0.000  0.00  0.00           C+0
CONECT    1    2    8   14                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    1                                                            
CONECT    9   10   15                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12   13   18                                                       
CONECT   13   12                                                            
CONECT   14   15   19    1                                                  
CONECT   15   14   16    9                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   12                                                  
CONECT   19   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0004259
HETATM    1  C1  UNL     1       3.135  -2.475   2.216  1.00  0.00           C  
HETATM    2  O1  UNL     1       1.902  -1.965   1.779  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.897  -0.716   1.156  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.049  -0.002   0.971  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.049   1.242   0.352  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.863   1.788  -0.094  1.00  0.00           C  
HETATM    7  N1  UNL     1       1.887   3.079  -0.660  1.00  0.00           N  
HETATM    8  C6  UNL     1       3.041   3.763  -1.052  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.229   3.435  -1.010  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.684   1.058   0.093  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.591   1.519  -0.392  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.745   2.575  -1.053  1.00  0.00           O  
HETATM   13  C9  UNL     1      -1.859   0.773  -0.150  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.128  -0.240  -1.226  1.00  0.00           C  
HETATM   15  N2  UNL     1      -3.348  -0.970  -1.009  1.00  0.00           N  
HETATM   16  C11 UNL     1      -3.589  -1.758   0.128  1.00  0.00           C  
HETATM   17  C12 UNL     1      -4.865  -2.482   0.287  1.00  0.00           C  
HETATM   18  O4  UNL     1      -2.720  -1.852   1.018  1.00  0.00           O  
HETATM   19  C13 UNL     1       0.704  -0.191   0.718  1.00  0.00           C  
HETATM   20  H1  UNL     1       3.874  -2.569   1.390  1.00  0.00           H  
HETATM   21  H2  UNL     1       3.030  -3.450   2.730  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.536  -1.757   2.970  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.022  -0.387   1.306  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.978   1.768   0.239  1.00  0.00           H  
HETATM   25  H6  UNL     1       0.952   3.571  -0.767  1.00  0.00           H  
HETATM   26  H7  UNL     1       2.880   4.784  -1.480  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.843   0.306   0.815  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.736   1.486  -0.144  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.105   0.256  -2.223  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.307  -0.984  -1.262  1.00  0.00           H  
HETATM   31  H12 UNL     1      -4.088  -0.887  -1.771  1.00  0.00           H  
HETATM   32  H13 UNL     1      -4.629  -3.505   0.627  1.00  0.00           H  
HETATM   33  H14 UNL     1      -5.507  -2.027   1.070  1.00  0.00           H  
HETATM   34  H15 UNL     1      -5.427  -2.468  -0.668  1.00  0.00           H  
HETATM   35  H16 UNL     1      -0.224  -0.719   0.839  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   23
CONECT    5    6    6   24
CONECT    6    7   10
CONECT    7    8   25
CONECT    8    9    9   26
CONECT   10   11   19   19
CONECT   11   12   12   13
CONECT   13   14   27   28
CONECT   14   15   29   30
CONECT   15   16   31
CONECT   16   17   18   18
CONECT   17   32   33   34
CONECT   19   35
END

HMDB0004259
     RDKit          3D
Acetyl-N-formyl-5-methoxykynurenamine
 35 35  0  0  0  0  0  0  0  0999 V2000
    3.1346   -2.4755    2.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9015   -1.9647    1.7791 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8968   -0.7160    1.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0491   -0.0021    0.9714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0490    1.2424    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8633    1.7883   -0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8870    3.0791   -0.6601 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0411    3.7632   -1.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2291    3.4349   -1.0102 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6841    1.0582    0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5905    1.5190   -0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454    2.5754   -1.0525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8586    0.7732   -0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1277   -0.2399   -1.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3485   -0.9702   -1.0092 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5893   -1.7582    0.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8654   -2.4820    0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7199   -1.8524    1.0183 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036   -0.1909    0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8741   -2.5691    1.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0300   -3.4498    2.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361   -1.7572    2.9695 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0215   -0.3872    1.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9784    1.7676    0.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9518    3.5708   -0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8802    4.7844   -1.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8433    0.3062    0.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7358    1.4859   -0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1052    0.2561   -2.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070   -0.9838   -1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0878   -0.8873   -1.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6290   -3.5046    0.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5071   -2.0265    1.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4266   -2.4679   -0.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2243   -0.7194    0.8389 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  6 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 10 19  2  0
 19  3  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 19 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Acetyl-N-formyl-5-methoxykynurenamine	HMDB
AFMK	HMDB
Formyl-N-acetyl-5-methoxykynurenamine	HMDB
N-[3-(2-Formamido-5-methoxy-phenyl)-3-oxo-propyl]acetamide	HMDB
N1-Acetyl-N2-formyl-5-methoxykynurenine	HMDB
NSC 688263	HMDB
K1	HMDB

Chemical Formula

C₁₃H₁₆N₂O₄

Average Molecular Weight

264.2771

Monoisotopic Molecular Weight

264.11100701

IUPAC Name

N-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide

Traditional Name

N-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide

CAS Registry Number

52450-38-1

SMILES

COC1=CC(C(=O)CCNC(C)=O)=C(NC=O)C=C1

InChI Identifier

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)

InChI Key

JYWNYMJKURVPFH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Methoxyaniline
Anilide
Phenoxy compound
Anisole
Benzoyl
Phenol ether
Methoxybenzene
N-arylamide
Aryl alkyl ketone
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Acetamide
Vinylogous amide
Secondary carboxylic acid amide
Carboxamide group
Ether
Carboxylic acid derivative
Hydrocarbon derivative
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

kynurenamines (CHEBI:28613 )
a small molecule (CPD-12022 )

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Meningitis (HMDB: HMDB0004259)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 12865098)
Cerebrospinal Fluid (CSF) (PMID: 16150112)
Cerebrospinal fluid (HMDB: HMDB0004259)

Excreta

Biofluid or Excreta

Feces (PMID: 26848182)

Cellular substructure

Cytoplasm (HMDB: HMDB0004259)

Source

Endogenous

Endogenous (HMDB: HMDB0004259)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (PathBank: SMP0063693)
Tryptophan Metabolism (HMDB: HMDB0004259)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-0.158	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	0.5	ALOGPS
logP	0.34	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.9	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	84.5 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	70.8 m³·mol⁻¹	ChemAxon
Polarizability	27.13 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	161.987	31661259
DarkChem	[M-H]-	159.415	31661259
DeepCCS	[M+H]+	162.724	30932474
DeepCCS	[M-H]-	160.366	30932474
DeepCCS	[M-2H]-	193.252	30932474
DeepCCS	[M+Na]+	168.818	30932474
AllCCS	[M+H]+	160.6	32859911
AllCCS	[M+H-H2O]+	157.1	32859911
AllCCS	[M+NH4]+	163.9	32859911
AllCCS	[M+Na]+	164.8	32859911
AllCCS	[M-H]-	161.9	32859911
AllCCS	[M+Na-2H]-	162.2	32859911
AllCCS	[M+HCOO]-	162.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.46 minutes	32390414
Predicted by Siyang on May 30, 2022	10.5844 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.29 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1577.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	241.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	120.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	69.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	297.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	411.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	106.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	806.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	338.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1157.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	265.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	281.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	324.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	188.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	105.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acetyl-N-formyl-5-methoxykynurenamine	COC1=CC(C(=O)CCNC(C)=O)=C(NC=O)C=C1	3805.9	Standard polar	33892256
Acetyl-N-formyl-5-methoxykynurenamine	COC1=CC(C(=O)CCNC(C)=O)=C(NC=O)C=C1	2604.3	Standard non polar	33892256
Acetyl-N-formyl-5-methoxykynurenamine	COC1=CC(C(=O)CCNC(C)=O)=C(NC=O)C=C1	2528.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Acetyl-N-formyl-5-methoxykynurenamine,1TMS,isomer #1	COC1=CC=C(NC=O)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C1	2555.1	Semi standard non polar	33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TMS,isomer #1	COC1=CC=C(NC=O)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C1	2672.1	Standard non polar	33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TMS,isomer #1	COC1=CC=C(NC=O)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C1	3499.4	Standard polar	33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TMS,isomer #2	COC1=CC=C(N(C=O)[Si](C)(C)C)C(C(=O)CCNC(C)=O)=C1	2452.0	Semi standard non polar	33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TMS,isomer #2	COC1=CC=C(N(C=O)[Si](C)(C)C)C(C(=O)CCNC(C)=O)=C1	2578.0	Standard non polar	33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TMS,isomer #2	COC1=CC=C(N(C=O)[Si](C)(C)C)C(C(=O)CCNC(C)=O)=C1	3240.7	Standard polar	33892256
Acetyl-N-formyl-5-methoxykynurenamine,2TMS,isomer #1	COC1=CC=C(N(C=O)[Si](C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C1	2367.6	Semi standard non polar	33892256
Acetyl-N-formyl-5-methoxykynurenamine,2TMS,isomer #1	COC1=CC=C(N(C=O)[Si](C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C1	2728.6	Standard non polar	33892256
Acetyl-N-formyl-5-methoxykynurenamine,2TMS,isomer #1	COC1=CC=C(N(C=O)[Si](C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C1	2968.8	Standard polar	33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TBDMS,isomer #1	COC1=CC=C(NC=O)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C1	2791.8	Semi standard non polar	33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TBDMS,isomer #1	COC1=CC=C(NC=O)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C1	2879.0	Standard non polar	33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TBDMS,isomer #1	COC1=CC=C(NC=O)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C1	3489.6	Standard polar	33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TBDMS,isomer #2	COC1=CC=C(N(C=O)[Si](C)(C)C(C)(C)C)C(C(=O)CCNC(C)=O)=C1	2722.3	Semi standard non polar	33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TBDMS,isomer #2	COC1=CC=C(N(C=O)[Si](C)(C)C(C)(C)C)C(C(=O)CCNC(C)=O)=C1	2763.2	Standard non polar	33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TBDMS,isomer #2	COC1=CC=C(N(C=O)[Si](C)(C)C(C)(C)C)C(C(=O)CCNC(C)=O)=C1	3312.9	Standard polar	33892256
Acetyl-N-formyl-5-methoxykynurenamine,2TBDMS,isomer #1	COC1=CC=C(N(C=O)[Si](C)(C)C(C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C1	2870.1	Semi standard non polar	33892256
Acetyl-N-formyl-5-methoxykynurenamine,2TBDMS,isomer #1	COC1=CC=C(N(C=O)[Si](C)(C)C(C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C1	3066.6	Standard non polar	33892256
Acetyl-N-formyl-5-methoxykynurenamine,2TBDMS,isomer #1	COC1=CC=C(N(C=O)[Si](C)(C)C(C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C1	3134.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine GC-EI-TOF (Non-derivatized)	splash10-001i-1790000000-08a018599da99d325111	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine GC-EI-TOF (Non-derivatized)	splash10-004r-1941000000-1fd6a7b0aa4a93746dce	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine GC-EI-TOF (Non-derivatized)	splash10-001i-1790000000-08a018599da99d325111	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine GC-EI-TOF (Non-derivatized)	splash10-004r-1941000000-1fd6a7b0aa4a93746dce	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kfy-8790000000-29b99509d4ad702e0c17	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 35V, Positive-QTOF	splash10-01ri-0900000000-befc2619a8b03b67929f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 35V, Negative-QTOF	splash10-0f79-1920000000-c1e957900fd03a536942	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 10V, Positive-QTOF	splash10-01bl-0190000000-cc0a8bf1c63ec5bda44d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 20V, Positive-QTOF	splash10-05dl-2970000000-e59ea14239ec95d81889	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 40V, Positive-QTOF	splash10-0fbc-4900000000-87c88186c3d6cd7b6c51	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 10V, Negative-QTOF	splash10-03dr-0090000000-6ea3042b8fae674f87bb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 20V, Negative-QTOF	splash10-00ku-3490000000-f9119264a2c3c8452765	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 40V, Negative-QTOF	splash10-052f-9110000000-7e684511197690c0f5cb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 10V, Negative-QTOF	splash10-03di-1190000000-9ea054e52d4b2713e40a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 20V, Negative-QTOF	splash10-0a4l-9420000000-5c7a32c26de619ab8544	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 40V, Negative-QTOF	splash10-0006-9410000000-be01b9cb02bd8503009a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 10V, Positive-QTOF	splash10-0170-0490000000-010747a672f5eb1374f0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 20V, Positive-QTOF	splash10-05bg-1950000000-b11b95cdcd40b6ee721a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 40V, Positive-QTOF	splash10-0kou-2900000000-ab1aed32a73b1f6ab74e	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000065 (0.000059-0.00189) uM	Adult (>18 years old)	Both	Normal	12865098	details
Cerebrospinal Fluid (CSF)	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	16150112	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.28 (0.06-0.50) uM	Adult (>18 years old)	Not Specified	Meningitis	16150112	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Iron deficiency	26848182	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	26848182	details

Associated Disorders and Diseases

Disease 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:16150112 ]
Iron deficiency
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Ulcerative colitis
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023355

KNApSAcK ID

Not Available

Chemspider ID

149637

KEGG Compound ID

C05642

BioCyc ID

Not Available

BiGG ID

46183

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

171161

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

FNA5MOXAM

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

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.

Material Safety Data Sheet (MSDS)

Download (PDF)

General 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:16150112 ]

Enzymes

Enzyme Details

1. Indoleamine 2,3-dioxygenase 1

General function:: Involved in heme binding
Specific function:: Catalyzes the cleavage of the pyrrol ring of tryptophan and incorporates both atoms of a molecule of oxygen.
Gene Name:: IDO1
Uniprot ID:: P14902
Molecular weight:: 45325.89

Reactions

Melatonin + Oxygen → Acetyl-N-formyl-5-methoxykynurenamine	details

Enzyme Details

2. Indoleamine 2,3-dioxygenase 2

General function:: Involved in heme binding
Specific function:: Catalyzes the first and rate-limiting step in the kynurenine pathway of tryptophan catabolism.
Gene Name:: IDO2
Uniprot ID:: Q6ZQW0
Molecular weight:: 47074.745

Reactions

Melatonin + Oxygen → Acetyl-N-formyl-5-methoxykynurenamine	details

Showing metabocard for Acetyl-N-formyl-5-methoxykynurenamine (HMDB0004259)

MOL for HMDB0004259 (Acetyl-N-formyl-5-methoxykynurenamine)

3D MOL for HMDB0004259 (Acetyl-N-formyl-5-methoxykynurenamine)

3D SDF for HMDB0004259 (Acetyl-N-formyl-5-methoxykynurenamine)

3D-SDF for HMDB0004259 (Acetyl-N-formyl-5-methoxykynurenamine)

PDB for HMDB0004259 (Acetyl-N-formyl-5-methoxykynurenamine)

3D PDB for HMDB0004259 (Acetyl-N-formyl-5-methoxykynurenamine)

SMILES for HMDB0004259 (Acetyl-N-formyl-5-methoxykynurenamine)

INCHI for HMDB0004259 (Acetyl-N-formyl-5-methoxykynurenamine)

Structure for HMDB0004259 (Acetyl-N-formyl-5-methoxykynurenamine)

3D Structure for HMDB0004259 (Acetyl-N-formyl-5-methoxykynurenamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions