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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2019-07-16 16:49:12 UTC

Update Date

2022-03-07 03:18:16 UTC

HMDB ID

HMDB0240369

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-Acetylaminophenoxazin-3-one

Description

2-Acetylaminophenoxazin-3-one, also known as 2-acetamido-3-phenoxazone or N-acetylquestiomycin a, belongs to the class of organic compounds known as phenoxazines. These are polycyclic aromatic compounds containing a phenoxazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a 1,4-oxazine ring. Based on a literature review very few articles have been published on 2-Acetylaminophenoxazin-3-one.

Structure

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

HMDB0240369
     RDKit          3D
2-Acetylaminophenoxazin-3-one
 29 31  0  0  0  0  0  0  0  0999 V2000
   -5.6011   -0.5980   -0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0918   -0.6282    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6016   -1.6337    0.5753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3985    0.4667   -0.4747 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9977    0.6537   -0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1074   -0.2762   -0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2614   -0.0928   -0.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1085   -1.0066    0.4355 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4589   -0.7824    0.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3430   -1.7101    0.8732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7148   -1.5280    0.8327 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1809   -0.3651    0.2646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3097    0.5813   -0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9378    0.3788   -0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318    1.2990   -0.6873 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8151    1.1130   -0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    2.0206   -1.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4508    1.8177   -1.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618    2.6868   -1.5502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0279   -0.0404    0.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8516   -0.1197   -0.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0017   -1.6517   -0.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9537    1.2872   -0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -1.1910    0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9915   -2.6271    1.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4052   -2.2791    1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2585   -0.1910    0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7183    1.4793   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2925    2.9370   -1.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18  5  1  0
 16  7  1  0
 14  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 17 29  1  0
M  END


  Mrv1652307161918492D          

 19 21  0  0  0  0            999 V2000
    0.3572    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2150    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151   -0.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9295    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  2  0  0  0  0
  8 12  1  0  0  0  0
  9 13  2  0  0  0  0
 10 14  2  0  0  0  0
 11 15  1  0  0  0  0
 13 16  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 15 16  2  0  0  0  0
 12 17  1  0  0  0  0
 17 19  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240369

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)NC1=CC2=NC3=CC=CC=C3OC2=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H10N2O3/c1-8(17)15-10-6-11-14(7-12(10)18)19-13-5-3-2-4-9(13)16-11/h2-7H,1H3,(H,15,17)

> <INCHI_KEY>
DWOBTNSFRDZSMA-UHFFFAOYSA-N

> <FORMULA>
C14H10N2O3

> <MOLECULAR_WEIGHT>
254.245

> <EXACT_MASS>
254.06914219

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
25.82376454979292

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(3-oxo-3H-phenoxazin-2-yl)acetamide

> <ALOGPS_LOGP>
1.78

> <JCHEM_LOGP>
1.0125960639999998

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.884396576667829

> <JCHEM_PKA_STRONGEST_BASIC>
-1.383418407585471

> <JCHEM_POLAR_SURFACE_AREA>
67.75999999999999

> <JCHEM_REFRACTIVITY>
73.0124

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(3-oxophenoxazin-2-yl)acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240369
     RDKit          3D
2-Acetylaminophenoxazin-3-one
 29 31  0  0  0  0  0  0  0  0999 V2000
   -5.6011   -0.5980   -0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0918   -0.6282    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6016   -1.6337    0.5753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3985    0.4667   -0.4747 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9977    0.6537   -0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1074   -0.2762   -0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2614   -0.0928   -0.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1085   -1.0066    0.4355 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4589   -0.7824    0.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3430   -1.7101    0.8732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7148   -1.5280    0.8327 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1809   -0.3651    0.2646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3097    0.5813   -0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9378    0.3788   -0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318    1.2990   -0.6873 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8151    1.1130   -0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    2.0206   -1.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4508    1.8177   -1.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618    2.6868   -1.5502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0279   -0.0404    0.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8516   -0.1197   -0.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0017   -1.6517   -0.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9537    1.2872   -0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -1.1910    0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9915   -2.6271    1.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4052   -2.2791    1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2585   -0.1910    0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7183    1.4793   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2925    2.9370   -1.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18  5  1  0
 16  7  1  0
 14  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 17 29  1  0
M  END

HEADER    PROTEIN                                 16-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-JUL-19         0                                  
HETATM    1  C   UNK     0       0.667   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.667  -0.770   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.667   1.540   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       2.001   1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.667  -1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.001  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.001   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.334   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.334   1.540   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       4.668   1.540   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -3.334  -1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.668  -1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.668   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.001   0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.002  -0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.335   1.540   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   11    9                                                  
CONECT    8    4   12   10                                                  
CONECT    9    5   13    7                                                  
CONECT   10    6   14    8                                                  
CONECT   11    7   15                                                       
CONECT   12    8   17                                                       
CONECT   13    9   16                                                       
CONECT   14   10                                                            
CONECT   15   11   16                                                       
CONECT   16   13   15                                                       
CONECT   17   12   19   18                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0240369
HETATM    1  C1  UNL     1      -5.601  -0.598  -0.021  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.092  -0.628   0.051  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.602  -1.634   0.575  1.00  0.00           O  
HETATM    4  N1  UNL     1      -3.398   0.467  -0.475  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.998   0.654  -0.517  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.107  -0.276  -0.015  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.261  -0.093  -0.056  1.00  0.00           C  
HETATM    8  N2  UNL     1       1.109  -1.007   0.436  1.00  0.00           N  
HETATM    9  C6  UNL     1       2.459  -0.782   0.373  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.343  -1.710   0.873  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.715  -1.528   0.833  1.00  0.00           C  
HETATM   12  C9  UNL     1       5.181  -0.365   0.265  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.310   0.581  -0.245  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.938   0.379  -0.194  1.00  0.00           C  
HETATM   15  O2  UNL     1       2.132   1.299  -0.687  1.00  0.00           O  
HETATM   16  C12 UNL     1       0.815   1.113  -0.643  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.094   2.021  -1.134  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.451   1.818  -1.082  1.00  0.00           C  
HETATM   19  O3  UNL     1      -2.262   2.687  -1.550  1.00  0.00           O  
HETATM   20  H1  UNL     1      -6.028  -0.040   0.833  1.00  0.00           H  
HETATM   21  H2  UNL     1      -5.852  -0.120  -0.989  1.00  0.00           H  
HETATM   22  H3  UNL     1      -6.002  -1.652  -0.076  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.954   1.287  -0.909  1.00  0.00           H  
HETATM   24  H5  UNL     1      -1.488  -1.191   0.431  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.991  -2.627   1.322  1.00  0.00           H  
HETATM   26  H7  UNL     1       5.405  -2.279   1.237  1.00  0.00           H  
HETATM   27  H8  UNL     1       6.258  -0.191   0.217  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.718   1.479  -0.681  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.292   2.937  -1.581  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3    4
CONECT    4    5   23
CONECT    5    6    6   18
CONECT    6    7   24
CONECT    7    8    8   16
CONECT    8    9
CONECT    9   10   10   14
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   12   13   27
CONECT   13   14   14   28
CONECT   14   15
CONECT   15   16
CONECT   16   17   17
CONECT   17   18   29
CONECT   18   19   19
END

HMDB0240369
     RDKit          3D
2-Acetylaminophenoxazin-3-one
 29 31  0  0  0  0  0  0  0  0999 V2000
   -5.6011   -0.5980   -0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0918   -0.6282    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6016   -1.6337    0.5753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3985    0.4667   -0.4747 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9977    0.6537   -0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1074   -0.2762   -0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2614   -0.0928   -0.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1085   -1.0066    0.4355 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4589   -0.7824    0.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3430   -1.7101    0.8732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7148   -1.5280    0.8327 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1809   -0.3651    0.2646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3097    0.5813   -0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9378    0.3788   -0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318    1.2990   -0.6873 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8151    1.1130   -0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    2.0206   -1.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4508    1.8177   -1.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618    2.6868   -1.5502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0279   -0.0404    0.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8516   -0.1197   -0.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0017   -1.6517   -0.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9537    1.2872   -0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -1.1910    0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9915   -2.6271    1.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4052   -2.2791    1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2585   -0.1910    0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7183    1.4793   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2925    2.9370   -1.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18  5  1  0
 16  7  1  0
 14  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 17 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-(3-oxo-3H-Phenoxazin-2-yl)ethanimidate	HMDB
2-(N-Acetylamino)-3-phenoxazone	HMDB
2-Acetamido-3-phenoxazone	HMDB
2-Acetaminophenoxazin-3-one	HMDB
2-Acetylamino-3H-phenoxazin-3-one	HMDB
N-(3-oxo-3H-Phenoxazin-2-yl)acetamide	HMDB
N-Acetyl-2-amino-3H-phenoxazin-3-one	HMDB
N-Acetylquestiomycin a	HMDB
2-Acetylaminophenoxazin-3-one	HMDB

Chemical Formula

C₁₄H₁₀N₂O₃

Average Molecular Weight

254.245

Monoisotopic Molecular Weight

254.06914219

IUPAC Name

N-(3-oxo-3H-phenoxazin-2-yl)acetamide

Traditional Name

N-(3-oxophenoxazin-2-yl)acetamide

CAS Registry Number

1916-55-8

SMILES

CC(=O)NC1=CC2=NC3=CC=CC=C3OC2=CC1=O

InChI Identifier

InChI=1S/C14H10N2O3/c1-8(17)15-10-6-11-14(7-12(10)18)19-13-5-3-2-4-9(13)16-11/h2-7H,1H3,(H,15,17)

InChI Key

DWOBTNSFRDZSMA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenoxazines. These are polycyclic aromatic compounds containing a phenoxazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a 1,4-oxazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazines

Sub Class

Phenoxazines

Direct Parent

Phenoxazines

Alternative Parents

Substituents

Phenoxazine
N-acetylarylamine
N-arylamide
Benzenoid
Heteroaromatic compound
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Cyclic ketone
Carboxylic acid derivative
Oxacycle
Azacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Source

Exogenous

Exogenous (HMDB: HMDB0240369)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.78	ALOGPS
logP	1.01	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	12.88	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	67.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.01 m³·mol⁻¹	ChemAxon
Polarizability	25.82 Å³	ChemAxon
Number of Rings	3	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
DeepCCS	[M+H]+	154.125	30932474
DeepCCS	[M-H]-	151.767	30932474
DeepCCS	[M-2H]-	184.78	30932474
DeepCCS	[M+Na]+	160.218	30932474
AllCCS	[M+H]+	156.1	32859911
AllCCS	[M+H-H2O]+	152.4	32859911
AllCCS	[M+NH4]+	159.6	32859911
AllCCS	[M+Na]+	160.6	32859911
AllCCS	[M-H]-	160.0	32859911
AllCCS	[M+Na-2H]-	159.4	32859911
AllCCS	[M+HCOO]-	158.8	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.	4.98 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6156 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.34 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1482.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	287.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	117.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	179.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	125.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	310.4 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	444.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	165.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	816.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	283.9 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	1029.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	276.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	272.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	315.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	197.7 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	92.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Acetylaminophenoxazin-3-one	CC(=O)NC1=CC2=NC3=CC=CC=C3OC2=CC1=O	3383.1	Standard polar	33892256
2-Acetylaminophenoxazin-3-one	CC(=O)NC1=CC2=NC3=CC=CC=C3OC2=CC1=O	2477.0	Standard non polar	33892256
2-Acetylaminophenoxazin-3-one	CC(=O)NC1=CC2=NC3=CC=CC=C3OC2=CC1=O	2579.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Acetylaminophenoxazin-3-one,1TMS,isomer #1	CC(=O)N(C1=CC2=NC3=CC=CC=C3OC2=CC1=O)[Si](C)(C)C	2678.6	Semi standard non polar	33892256
2-Acetylaminophenoxazin-3-one,1TMS,isomer #1	CC(=O)N(C1=CC2=NC3=CC=CC=C3OC2=CC1=O)[Si](C)(C)C	2625.3	Standard non polar	33892256
2-Acetylaminophenoxazin-3-one,1TMS,isomer #1	CC(=O)N(C1=CC2=NC3=CC=CC=C3OC2=CC1=O)[Si](C)(C)C	3363.1	Standard polar	33892256
2-Acetylaminophenoxazin-3-one,1TBDMS,isomer #1	CC(=O)N(C1=CC2=NC3=CC=CC=C3OC2=CC1=O)[Si](C)(C)C(C)(C)C	2900.9	Semi standard non polar	33892256
2-Acetylaminophenoxazin-3-one,1TBDMS,isomer #1	CC(=O)N(C1=CC2=NC3=CC=CC=C3OC2=CC1=O)[Si](C)(C)C(C)(C)C	2822.3	Standard non polar	33892256
2-Acetylaminophenoxazin-3-one,1TBDMS,isomer #1	CC(=O)N(C1=CC2=NC3=CC=CC=C3OC2=CC1=O)[Si](C)(C)C(C)(C)C	3402.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Acetylaminophenoxazin-3-one 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 - 2-Acetylaminophenoxazin-3-one 10V, Positive-QTOF	splash10-08fr-0090000000-c13b512a2163871a57f7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetylaminophenoxazin-3-one 20V, Positive-QTOF	splash10-03di-0090000000-577856e5ef81f7fd4ef6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetylaminophenoxazin-3-one 40V, Positive-QTOF	splash10-08fr-0890000000-32f92429da0bd7a643c2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetylaminophenoxazin-3-one 10V, Negative-QTOF	splash10-0w29-0090000000-636f8a65e9b27e4b8251	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetylaminophenoxazin-3-one 20V, Negative-QTOF	splash10-03di-0090000000-110769cb8520d4f26a65	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetylaminophenoxazin-3-one 40V, Negative-QTOF	splash10-01qi-0490000000-70068c4f5b09921da7f4	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

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

167772

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

193337

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Adhikari KB, Laerke HN, Mortensen AG, Fomsgaard IS: Plasma and urine concentrations of bioactive dietary benzoxazinoids and their glucuronidated conjugates in rats fed a rye bread-based diet. J Agric Food Chem. 2012 Nov 21;60(46):11518-24. doi: 10.1021/jf301737n. Epub 2012 Nov 12. [PubMed:23113707 ]
Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]

Showing metabocard for 2-Acetylaminophenoxazin-3-one (HMDB0240369)

MOL for HMDB0240369 (2-Acetylaminophenoxazin-3-one)

3D MOL for HMDB0240369 (2-Acetylaminophenoxazin-3-one)

3D SDF for HMDB0240369 (2-Acetylaminophenoxazin-3-one)

3D-SDF for HMDB0240369 (2-Acetylaminophenoxazin-3-one)

PDB for HMDB0240369 (2-Acetylaminophenoxazin-3-one)

3D PDB for HMDB0240369 (2-Acetylaminophenoxazin-3-one)

SMILES for HMDB0240369 (2-Acetylaminophenoxazin-3-one)

INCHI for HMDB0240369 (2-Acetylaminophenoxazin-3-one)

Structure for HMDB0240369 (2-Acetylaminophenoxazin-3-one)

3D Structure for HMDB0240369 (2-Acetylaminophenoxazin-3-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra