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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-23 02:41:03 UTC

Update Date

2022-03-07 03:17:55 UTC

HMDB ID

HMDB0062497

Secondary Accession Numbers

HMDB62497

Metabolite Identification

Common Name

N-Acetyl-5-methoxykynuramine

Description

N-Acetyl-5-methoxykynuramine (AMK) is a melatonin metabolite. Its direct precursor, acetyl-N-formyl-5-methoxykynurenamine (AFMK), is a product of melatonin metabolization in the brain (PMID: 23963910 ). AMK is a potent scavenger of several reactive oxygen species (ROS) such as hydroxyl, peroxyl, and carbonate radicals as well as the non-radical singlet oxygen (PMID: 14599344 , 18643875 ).

Structure

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

HMDB0062497
     RDKit          3D
N-Acetyl-5-methoxykynuramine
 33 33  0  0  0  0  0  0  0  0999 V2000
    5.4911   -0.9660    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1745   -1.0195   -0.4115 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1629   -0.1912    0.0953 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4066    0.7064    1.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3966    1.5180    1.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1207    1.4660    1.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0936    2.3109    1.6214 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8591    0.5744    0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4744    0.4965   -0.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3686    1.2387   -0.0055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7691   -0.4538   -1.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126   -0.3904   -1.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1187   -0.7030   -0.9176 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5306   -0.7119   -1.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4382   -1.0381    0.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9889   -0.4289   -2.2246 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8839   -0.2461   -0.4098 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3802   -1.0127    1.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9869    0.0131   -0.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1083   -1.8041   -0.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4169    0.7591    1.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6189    2.2133    2.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2390    2.1821    2.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328    3.0552    1.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0802   -0.3645   -2.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6159   -1.5073   -1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4882    0.6053   -2.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3316   -1.1121   -2.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6912   -0.9317    0.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5227   -2.1393    0.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4422   -0.6099   -0.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1307   -0.5730    0.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6752   -0.9355   -1.1996 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
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
  8 17  2  0
 17  3  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
 11 25  1  0
 11 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 17 33  1  0
M  END

  Mrv1652301231818312D          

 17 17  0  0  0  0            999 V2000
 9998.0681 9999.8117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7831 9999.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5003 9999.8117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.2156 9999.4004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.9329 9999.8117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6481 9999.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.932910000.6386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.068110000.6386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6380 9997.3316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9179 9996.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.638010000.6386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6366 9999.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9223 9999.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9223 9998.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6366 9998.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3510 9998.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3510 9999.3987    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
 12 13  2  0  0  0  0
 13 14  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 12  1  0  0  0  0
 12 11  1  0  0  0  0
 15  9  1  0  0  0  0
  1 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062497

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H16N2O3/c1-8(15)14-6-5-12(16)10-7-9(17-2)3-4-11(10)13/h3-4,7H,5-6,13H2,1-2H3,(H,14,15)

> <INCHI_KEY>
RJQIZOKNUKRKTP-UHFFFAOYSA-N

> <FORMULA>
C12H16N2O3

> <MOLECULAR_WEIGHT>
236.271

> <EXACT_MASS>
236.116092383

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.30328664116603

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.40

> <JCHEM_LOGP>
0.3260256116666669

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.538171938084282

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.217804437831614

> <JCHEM_PKA_STRONGEST_BASIC>
3.189598278797957

> <JCHEM_POLAR_SURFACE_AREA>
81.42

> <JCHEM_REFRACTIVITY>
65.1273

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.18e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062497
     RDKit          3D
N-Acetyl-5-methoxykynuramine
 33 33  0  0  0  0  0  0  0  0999 V2000
    5.4911   -0.9660    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1745   -1.0195   -0.4115 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1629   -0.1912    0.0953 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4066    0.7064    1.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3966    1.5180    1.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1207    1.4660    1.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0936    2.3109    1.6214 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8591    0.5744    0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4744    0.4965   -0.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3686    1.2387   -0.0055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7691   -0.4538   -1.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126   -0.3904   -1.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1187   -0.7030   -0.9176 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5306   -0.7119   -1.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4382   -1.0381    0.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9889   -0.4289   -2.2246 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8839   -0.2461   -0.4098 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3802   -1.0127    1.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9869    0.0131   -0.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1083   -1.8041   -0.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4169    0.7591    1.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6189    2.2133    2.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2390    2.1821    2.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328    3.0552    1.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0802   -0.3645   -2.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6159   -1.5073   -1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4882    0.6053   -2.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3316   -1.1121   -2.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6912   -0.9317    0.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5227   -2.1393    0.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4422   -0.6099   -0.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1307   -0.5730    0.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6752   -0.9355   -1.1996 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
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
  8 17  2  0
 17  3  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
 11 25  1  0
 11 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 17 33  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    8663.0608666.315   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.3958665.547   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8665.7348666.315   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0    8667.0698665.547   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0    8668.4088666.315   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8669.7438665.547   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8668.4088667.859   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8663.0608667.859   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8660.3918661.686   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8659.0478660.912   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0    8660.3918667.859   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0    8660.3888666.314   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8659.0558665.544   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8659.0558664.004   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8660.3888663.234   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8661.7228664.004   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8661.7228665.544   0.000  0.00  0.00           C+0
CONECT    1    2    8   17                                                  
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                                                            
CONECT   11   12                                                            
CONECT   12   13   17   11                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16    9                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12    1                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0062497
HETATM    1  C1  UNL     1       5.491  -0.966   0.106  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.175  -1.020  -0.411  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.163  -0.191   0.095  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.407   0.706   1.114  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.397   1.518   1.604  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.121   1.466   1.103  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.094   2.311   1.621  1.00  0.00           N  
HETATM    8  C6  UNL     1       0.859   0.574   0.084  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.474   0.497  -0.464  1.00  0.00           C  
HETATM   10  O2  UNL     1      -1.369   1.239  -0.005  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.769  -0.454  -1.555  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.213  -0.390  -1.995  1.00  0.00           C  
HETATM   13  N2  UNL     1      -3.119  -0.703  -0.918  1.00  0.00           N  
HETATM   14  C10 UNL     1      -4.531  -0.712  -1.075  1.00  0.00           C  
HETATM   15  C11 UNL     1      -5.438  -1.038   0.054  1.00  0.00           C  
HETATM   16  O3  UNL     1      -4.989  -0.429  -2.225  1.00  0.00           O  
HETATM   17  C12 UNL     1       1.884  -0.246  -0.410  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.380  -1.013   1.229  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.987   0.013  -0.096  1.00  0.00           H  
HETATM   20  H3  UNL     1       6.108  -1.804  -0.213  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.417   0.759   1.522  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.619   2.213   2.405  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.239   2.182   2.589  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.333   3.055   1.055  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.080  -0.365  -2.418  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.616  -1.507  -1.177  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.488   0.605  -2.395  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.332  -1.112  -2.833  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.691  -0.932   0.019  1.00  0.00           H  
HETATM   30  H13 UNL     1      -5.523  -2.139   0.208  1.00  0.00           H  
HETATM   31  H14 UNL     1      -6.442  -0.610  -0.206  1.00  0.00           H  
HETATM   32  H15 UNL     1      -5.131  -0.573   0.995  1.00  0.00           H  
HETATM   33  H16 UNL     1       1.675  -0.935  -1.200  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5   21
CONECT    5    6    6   22
CONECT    6    7    8
CONECT    7   23   24
CONECT    8    9   17   17
CONECT    9   10   10   11
CONECT   11   12   25   26
CONECT   12   13   27   28
CONECT   13   14   29
CONECT   14   15   16   16
CONECT   15   30   31   32
CONECT   17   33
END

HMDB0062497
     RDKit          3D
N-Acetyl-5-methoxykynuramine
 33 33  0  0  0  0  0  0  0  0999 V2000
    5.4911   -0.9660    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1745   -1.0195   -0.4115 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1629   -0.1912    0.0953 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4066    0.7064    1.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3966    1.5180    1.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1207    1.4660    1.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0936    2.3109    1.6214 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8591    0.5744    0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4744    0.4965   -0.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3686    1.2387   -0.0055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7691   -0.4538   -1.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126   -0.3904   -1.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1187   -0.7030   -0.9176 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5306   -0.7119   -1.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4382   -1.0381    0.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9889   -0.4289   -2.2246 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8839   -0.2461   -0.4098 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3802   -1.0127    1.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9869    0.0131   -0.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1083   -1.8041   -0.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4169    0.7591    1.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6189    2.2133    2.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2390    2.1821    2.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328    3.0552    1.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0802   -0.3645   -2.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6159   -1.5073   -1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4882    0.6053   -2.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3316   -1.1121   -2.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6912   -0.9317    0.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5227   -2.1393    0.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4422   -0.6099   -0.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1307   -0.5730    0.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6752   -0.9355   -1.1996 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
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
  8 17  2  0
 17  3  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
 11 25  1  0
 11 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 17 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N(gamma)-Acetyl-5-methoxykynurenamine	MeSH
N-Acetyl-5-methoxy kynurenamine	MeSH
N(1)-Acetyl-5-methoxykynuramine	MeSH
AMK kynuramine CPD	MeSH
AMKA	HMDB
N1-Acetyl-5-methoxykynuramine	HMDB
NSC 688265	HMDB
AMK	HMDB
K2	HMDB

Chemical Formula

C₁₂H₁₆N₂O₃

Average Molecular Weight

236.271

Monoisotopic Molecular Weight

236.116092383

IUPAC Name

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

Traditional Name

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

CAS Registry Number

52450-39-2

SMILES

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

InChI Identifier

InChI=1S/C12H16N2O3/c1-8(15)14-6-5-12(16)10-7-9(17-2)3-4-11(10)13/h3-4,7H,5-6,13H2,1-2H3,(H,14,15)

InChI Key

RJQIZOKNUKRKTP-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
Aminophenyl ether
Methoxyaniline
Phenoxy compound
Anisole
Benzoyl
Methoxybenzene
Aniline or substituted anilines
Aryl alkyl ketone
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Acetamide
Vinylogous amide
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Ether
Carboxylic acid derivative
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organic nitrogen compound
Primary amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

a small molecule (CPD-12023 )

Ontology

Not Available

Exogenous (HMDB: HMDB0062497)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.72 g/l	ALOGPS
LogP	0.40	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.4	ALOGPS
logP	0.33	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	15.22	ChemAxon
pKa (Strongest Basic)	3.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	81.42 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	65.13 m³·mol⁻¹	ChemAxon
Polarizability	25.3 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]+	156.429	31661259
DarkChem	[M-H]-	155.358	31661259
DeepCCS	[M+H]+	156.466	30932474
DeepCCS	[M-H]-	154.108	30932474
DeepCCS	[M-2H]-	187.383	30932474
DeepCCS	[M+Na]+	162.559	30932474
AllCCS	[M+H]+	154.2	32859911
AllCCS	[M+H-H2O]+	150.5	32859911
AllCCS	[M+NH4]+	157.7	32859911
AllCCS	[M+Na]+	158.7	32859911
AllCCS	[M-H]-	156.3	32859911
AllCCS	[M+Na-2H]-	156.8	32859911
AllCCS	[M+HCOO]-	157.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-5-methoxykynuramine	COC1=CC=C(N)C(=C1)C(=O)CCNC(C)=O	3501.9	Standard polar	33892256
N-Acetyl-5-methoxykynuramine	COC1=CC=C(N)C(=C1)C(=O)CCNC(C)=O	2343.1	Standard non polar	33892256
N-Acetyl-5-methoxykynuramine	COC1=CC=C(N)C(=C1)C(=O)CCNC(C)=O	2347.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-5-methoxykynuramine,1TMS,isomer #1	COC1=CC=C(N[Si](C)(C)C)C(C(=O)CCNC(C)=O)=C1	2389.8	Semi standard non polar	33892256
N-Acetyl-5-methoxykynuramine,1TMS,isomer #1	COC1=CC=C(N[Si](C)(C)C)C(C(=O)CCNC(C)=O)=C1	2381.6	Standard non polar	33892256
N-Acetyl-5-methoxykynuramine,1TMS,isomer #1	COC1=CC=C(N[Si](C)(C)C)C(C(=O)CCNC(C)=O)=C1	3099.0	Standard polar	33892256
N-Acetyl-5-methoxykynuramine,1TMS,isomer #2	COC1=CC=C(N)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C1	2266.7	Semi standard non polar	33892256
N-Acetyl-5-methoxykynuramine,1TMS,isomer #2	COC1=CC=C(N)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C1	2429.3	Standard non polar	33892256
N-Acetyl-5-methoxykynuramine,1TMS,isomer #2	COC1=CC=C(N)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C1	3322.6	Standard polar	33892256
N-Acetyl-5-methoxykynuramine,2TMS,isomer #1	COC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C(=O)CCNC(C)=O)=C1	2377.6	Semi standard non polar	33892256
N-Acetyl-5-methoxykynuramine,2TMS,isomer #1	COC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C(=O)CCNC(C)=O)=C1	2441.5	Standard non polar	33892256
N-Acetyl-5-methoxykynuramine,2TMS,isomer #1	COC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C(=O)CCNC(C)=O)=C1	2828.7	Standard polar	33892256
N-Acetyl-5-methoxykynuramine,2TMS,isomer #2	COC1=CC=C(N[Si](C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C1	2364.8	Semi standard non polar	33892256
N-Acetyl-5-methoxykynuramine,2TMS,isomer #2	COC1=CC=C(N[Si](C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C1	2549.6	Standard non polar	33892256
N-Acetyl-5-methoxykynuramine,2TMS,isomer #2	COC1=CC=C(N[Si](C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C1	2796.9	Standard polar	33892256
N-Acetyl-5-methoxykynuramine,3TMS,isomer #1	COC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C1	2326.8	Semi standard non polar	33892256
N-Acetyl-5-methoxykynuramine,3TMS,isomer #1	COC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C1	2586.3	Standard non polar	33892256
N-Acetyl-5-methoxykynuramine,3TMS,isomer #1	COC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C1	2617.4	Standard polar	33892256
N-Acetyl-5-methoxykynuramine,1TBDMS,isomer #1	COC1=CC=C(N[Si](C)(C)C(C)(C)C)C(C(=O)CCNC(C)=O)=C1	2648.4	Semi standard non polar	33892256
N-Acetyl-5-methoxykynuramine,1TBDMS,isomer #1	COC1=CC=C(N[Si](C)(C)C(C)(C)C)C(C(=O)CCNC(C)=O)=C1	2626.0	Standard non polar	33892256
N-Acetyl-5-methoxykynuramine,1TBDMS,isomer #1	COC1=CC=C(N[Si](C)(C)C(C)(C)C)C(C(=O)CCNC(C)=O)=C1	3115.2	Standard polar	33892256
N-Acetyl-5-methoxykynuramine,1TBDMS,isomer #2	COC1=CC=C(N)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C1	2518.0	Semi standard non polar	33892256
N-Acetyl-5-methoxykynuramine,1TBDMS,isomer #2	COC1=CC=C(N)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C1	2626.2	Standard non polar	33892256
N-Acetyl-5-methoxykynuramine,1TBDMS,isomer #2	COC1=CC=C(N)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C1	3303.4	Standard polar	33892256
N-Acetyl-5-methoxykynuramine,2TBDMS,isomer #1	COC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C(=O)CCNC(C)=O)=C1	2857.4	Semi standard non polar	33892256
N-Acetyl-5-methoxykynuramine,2TBDMS,isomer #1	COC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C(=O)CCNC(C)=O)=C1	2832.5	Standard non polar	33892256
N-Acetyl-5-methoxykynuramine,2TBDMS,isomer #1	COC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C(=O)CCNC(C)=O)=C1	2946.9	Standard polar	33892256
N-Acetyl-5-methoxykynuramine,2TBDMS,isomer #2	COC1=CC=C(N[Si](C)(C)C(C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C1	2828.1	Semi standard non polar	33892256
N-Acetyl-5-methoxykynuramine,2TBDMS,isomer #2	COC1=CC=C(N[Si](C)(C)C(C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C1	2944.0	Standard non polar	33892256
N-Acetyl-5-methoxykynuramine,2TBDMS,isomer #2	COC1=CC=C(N[Si](C)(C)C(C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C1	2951.4	Standard polar	33892256
N-Acetyl-5-methoxykynuramine,3TBDMS,isomer #1	COC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C1	3031.6	Semi standard non polar	33892256
N-Acetyl-5-methoxykynuramine,3TBDMS,isomer #1	COC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C1	3123.7	Standard non polar	33892256
N-Acetyl-5-methoxykynuramine,3TBDMS,isomer #1	COC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C1	2916.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-5-methoxykynuramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fdo-7910000000-4b4cff2213e82830e6d4	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-5-methoxykynuramine GC-MS (1 TMS) - 70eV, Positive	splash10-0g6u-5930000000-6ce1c368022077642916	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-5-methoxykynuramine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-5-methoxykynuramine 10V, Positive-QTOF	splash10-009f-0970000000-7034223f331e657c7930	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-5-methoxykynuramine 20V, Positive-QTOF	splash10-004l-0900000000-0eccf0c5393310c4979d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-5-methoxykynuramine 40V, Positive-QTOF	splash10-0uk9-6900000000-0a46d5a2db1495007b7e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-5-methoxykynuramine 10V, Negative-QTOF	splash10-000i-0290000000-43d86bc62c5ff336dc0f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-5-methoxykynuramine 20V, Negative-QTOF	splash10-054x-3930000000-469f58c9cb19e27a7451	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-5-methoxykynuramine 40V, Negative-QTOF	splash10-0a4l-9300000000-6dfc9c0b2457a7fe8680	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-5-methoxykynuramine 10V, Negative-QTOF	splash10-069c-2970000000-5b74ef865226c9e9cf0d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-5-methoxykynuramine 20V, Negative-QTOF	splash10-0a4i-9300000000-ac01793b610aa6742a53	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-5-methoxykynuramine 40V, Negative-QTOF	splash10-0007-9700000000-cf809475e37e838ef929	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-5-methoxykynuramine 10V, Positive-QTOF	splash10-002r-1960000000-96c4a29280101eb0c691	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-5-methoxykynuramine 20V, Positive-QTOF	splash10-00fs-2900000000-d7882f58c4e83b79eb57	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-5-methoxykynuramine 40V, Positive-QTOF	splash10-00dl-8900000000-372e79842e71fb34bafc	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

390658

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

CE5860

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Hugel HM, Jones OA: Natural product chemistry in action: the synthesis of melatonin metabolites K(1) and K(2). Methods Mol Biol. 2013;1055:163-70. doi: 10.1007/978-1-62703-577-4_12. [PubMed:23963910 ]
Ressmeyer AR, Mayo JC, Zelosko V, Sainz RM, Tan DX, Poeggeler B, Antolin I, Zsizsik BK, Reiter RJ, Hardeland R: Antioxidant properties of the melatonin metabolite N1-acetyl-5-methoxykynuramine (AMK): scavenging of free radicals and prevention of protein destruction. Redox Rep. 2003;8(4):205-13. doi: 10.1179/135100003225002709. [PubMed:14599344 ]
Schaefer M, Hardeland R: The melatonin metabolite N-acetyl-5-methoxykynuramine is a potent singlet oxygen scavenger. J Pineal Res. 2009 Jan;46(1):49-52. doi: 10.1111/j.1600-079X.2008.00614.x. Epub 2008 Jun 28. [PubMed:18643875 ]

Showing metabocard for N-Acetyl-5-methoxykynuramine (HMDB0062497)

MOL for HMDB0062497 (N-Acetyl-5-methoxykynuramine)

3D MOL for HMDB0062497 (N-Acetyl-5-methoxykynuramine)

3D SDF for HMDB0062497 (N-Acetyl-5-methoxykynuramine)

3D-SDF for HMDB0062497 (N-Acetyl-5-methoxykynuramine)

PDB for HMDB0062497 (N-Acetyl-5-methoxykynuramine)

3D PDB for HMDB0062497 (N-Acetyl-5-methoxykynuramine)

SMILES for HMDB0062497 (N-Acetyl-5-methoxykynuramine)

INCHI for HMDB0062497 (N-Acetyl-5-methoxykynuramine)

Structure for HMDB0062497 (N-Acetyl-5-methoxykynuramine)

3D Structure for HMDB0062497 (N-Acetyl-5-methoxykynuramine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra