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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:21:26 UTC

Update Date

2021-09-26 23:12:43 UTC

HMDB ID

HMDB0256775

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Prinomide

Description

Prinomide, also known as CGS-10787-b, belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution. Based on a literature review very few articles have been published on Prinomide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Prinomide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Prinomide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0256775
     RDKit          3D
Prinomide
 33 34  0  0  0  0  0  0  0  0999 V2000
    3.5472   -1.4792    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8638   -0.0689    0.0497 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1608    0.3896    0.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1612    1.7282   -0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8796    2.1371   -0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0633    0.9816   -0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6164    1.0373   -0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0763    2.1953   -0.4421 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7289   -0.0998   -0.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8281   -0.7315    1.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8854   -1.2209    2.2892 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7213    0.3297   -0.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9434    1.5056   -0.4870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7002   -0.6642   -0.1382 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0990   -0.4454   -0.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6834    0.7680   -0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0556    0.9223   -0.6646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8871   -0.1776   -0.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3337   -1.4163   -0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9889   -1.5255   -0.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7924   -1.8729   -0.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4260   -1.7767    1.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4996   -2.0616   -0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0467   -0.2460    0.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0227    2.3879   -0.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    3.1510   -0.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8712   -0.8073   -0.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4172   -1.6808    0.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1001    1.6631   -0.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4761    1.9076   -0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9643   -0.0727   -0.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0200   -2.2528   -0.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5708   -2.5042    0.0741 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  2  0
  7  9  1  0
  9 10  1  0
 10 11  3  0
  9 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6  2  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  9 27  1  0
 14 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  0
M  END

  Mrv1652309112119212D          

 20 21  0  0  0  0            999 V2000
   -0.9252   -3.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7537   -2.8106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057   -2.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8932   -1.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0862   -1.6545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  3  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256775

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C=CC=C1C(=O)C(C#N)C(=O)NC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H13N3O2/c1-18-9-5-8-13(18)14(19)12(10-16)15(20)17-11-6-3-2-4-7-11/h2-9,12H,1H3,(H,17,20)

> <INCHI_KEY>
KBQUAIAGRLAZGP-UHFFFAOYSA-N

> <FORMULA>
C15H13N3O2

> <MOLECULAR_WEIGHT>
267.288

> <EXACT_MASS>
267.100776671

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.70240367366641

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-cyano-3-(1-methyl-1H-pyrrol-2-yl)-3-oxo-N-phenylpropanamide

> <ALOGPS_LOGP>
2.20

> <JCHEM_LOGP>
1.873612724333333

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.265444517861717

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.401188297949378

> <JCHEM_PKA_STRONGEST_BASIC>
-8.306744461748618

> <JCHEM_POLAR_SURFACE_AREA>
74.89

> <JCHEM_REFRACTIVITY>
75.88620000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-cyano-3-(1-methylpyrrol-2-yl)-3-oxo-N-phenylpropanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256775
     RDKit          3D
Prinomide
 33 34  0  0  0  0  0  0  0  0999 V2000
    3.5472   -1.4792    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8638   -0.0689    0.0497 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1608    0.3896    0.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1612    1.7282   -0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8796    2.1371   -0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0633    0.9816   -0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6164    1.0373   -0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0763    2.1953   -0.4421 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7289   -0.0998   -0.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8281   -0.7315    1.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8854   -1.2209    2.2892 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7213    0.3297   -0.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9434    1.5056   -0.4870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7002   -0.6642   -0.1382 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0990   -0.4454   -0.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6834    0.7680   -0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0556    0.9223   -0.6646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8871   -0.1776   -0.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3337   -1.4163   -0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9889   -1.5255   -0.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7924   -1.8729   -0.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4260   -1.7767    1.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4996   -2.0616   -0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0467   -0.2460    0.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0227    2.3879   -0.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    3.1510   -0.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8712   -0.8073   -0.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4172   -1.6808    0.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1001    1.6631   -0.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4761    1.9076   -0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9643   -0.0727   -0.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0200   -2.2528   -0.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5708   -2.5042    0.0741 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  2  0
  7  9  1  0
  9 10  1  0
 10 11  3  0
  9 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6  2  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  9 27  1  0
 14 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -1.727  -6.753   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -1.407  -5.246   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -2.437  -4.102   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.667  -2.768   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.161  -3.088   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.667  -1.540   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       5.335  -4.620   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0256775
HETATM    1  C1  UNL     1       3.547  -1.479   0.213  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.864  -0.069   0.050  1.00  0.00           N  
HETATM    3  C2  UNL     1       5.161   0.390   0.068  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.161   1.728  -0.112  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.880   2.137  -0.246  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.063   0.982  -0.140  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.616   1.037  -0.222  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.076   2.195  -0.442  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.729  -0.100  -0.074  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.828  -0.731   1.250  1.00  0.00           C  
HETATM   11  N2  UNL     1       0.885  -1.221   2.289  1.00  0.00           N  
HETATM   12  C9  UNL     1      -0.721   0.330  -0.254  1.00  0.00           C  
HETATM   13  O2  UNL     1      -0.943   1.506  -0.487  1.00  0.00           O  
HETATM   14  N3  UNL     1      -1.700  -0.664  -0.138  1.00  0.00           N  
HETATM   15  C10 UNL     1      -3.099  -0.445  -0.276  1.00  0.00           C  
HETATM   16  C11 UNL     1      -3.683   0.768  -0.541  1.00  0.00           C  
HETATM   17  C12 UNL     1      -5.056   0.922  -0.665  1.00  0.00           C  
HETATM   18  C13 UNL     1      -5.887  -0.178  -0.518  1.00  0.00           C  
HETATM   19  C14 UNL     1      -5.334  -1.416  -0.250  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.989  -1.525  -0.136  1.00  0.00           C  
HETATM   21  H1  UNL     1       2.792  -1.873  -0.469  1.00  0.00           H  
HETATM   22  H2  UNL     1       3.426  -1.777   1.278  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.500  -2.062  -0.081  1.00  0.00           H  
HETATM   24  H4  UNL     1       6.047  -0.246   0.209  1.00  0.00           H  
HETATM   25  H5  UNL     1       6.023   2.388  -0.148  1.00  0.00           H  
HETATM   26  H6  UNL     1       3.491   3.151  -0.406  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.871  -0.807  -0.914  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.417  -1.681   0.069  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.100   1.663  -0.667  1.00  0.00           H  
HETATM   30  H10 UNL     1      -5.476   1.908  -0.877  1.00  0.00           H  
HETATM   31  H11 UNL     1      -6.964  -0.073  -0.612  1.00  0.00           H  
HETATM   32  H12 UNL     1      -6.020  -2.253  -0.142  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.571  -2.504   0.074  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    6
CONECT    3    4    4   24
CONECT    4    5   25
CONECT    5    6    6   26
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   12   27
CONECT   10   11   11   11
CONECT   12   13   13   14
CONECT   14   15   28
CONECT   15   16   16   20
CONECT   16   17   29
CONECT   17   18   18   30
CONECT   18   19   31
CONECT   19   20   20   32
CONECT   20   33
END

HMDB0256775
     RDKit          3D
Prinomide
 33 34  0  0  0  0  0  0  0  0999 V2000
    3.5472   -1.4792    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8638   -0.0689    0.0497 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1608    0.3896    0.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1612    1.7282   -0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8796    2.1371   -0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0633    0.9816   -0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6164    1.0373   -0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0763    2.1953   -0.4421 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7289   -0.0998   -0.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8281   -0.7315    1.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8854   -1.2209    2.2892 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7213    0.3297   -0.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9434    1.5056   -0.4870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7002   -0.6642   -0.1382 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0990   -0.4454   -0.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6834    0.7680   -0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0556    0.9223   -0.6646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8871   -0.1776   -0.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3337   -1.4163   -0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9889   -1.5255   -0.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7924   -1.8729   -0.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4260   -1.7767    1.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4996   -2.0616   -0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0467   -0.2460    0.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0227    2.3879   -0.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    3.1510   -0.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8712   -0.8073   -0.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4172   -1.6808    0.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1001    1.6631   -0.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4761    1.9076   -0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9643   -0.0727   -0.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0200   -2.2528   -0.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5708   -2.5042    0.0741 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  2  0
  7  9  1  0
  9 10  1  0
 10 11  3  0
  9 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6  2  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  9 27  1  0
 14 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Cyano-3-(1-methyl-1H-pyrrol-2-yl)-3-oxo-N-phenylpropanimidate	HMDB
1-Methyl-beta-oxo-alpha-(phenylcarbamoyl)-2-pyrrolepropionitrile 2-(N,N-bis(2-hydroxyethyl)amino)ethanol (1:1)salt	HMDB
CGS-10787-b	HMDB

Chemical Formula

C₁₅H₁₃N₃O₂

Average Molecular Weight

267.288

Monoisotopic Molecular Weight

267.100776671

IUPAC Name

2-cyano-3-(1-methyl-1H-pyrrol-2-yl)-3-oxo-N-phenylpropanamide

Traditional Name

2-cyano-3-(1-methylpyrrol-2-yl)-3-oxo-N-phenylpropanamide

CAS Registry Number

Not Available

SMILES

CN1C=CC=C1C(=O)C(C#N)C(=O)NC1=CC=CC=C1

InChI Identifier

InChI=1S/C15H13N3O2/c1-18-9-5-8-13(18)14(19)12(10-16)15(20)17-11-6-3-2-4-7-11/h2-9,12H,1H3,(H,17,20)

InChI Key

KBQUAIAGRLAZGP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Anilides

Alternative Parents

Substituents

Anilide
Aryl alkyl ketone
Aryl ketone
N-arylamide
Fatty amide
N-methylpyrrole
Fatty acyl
Substituted pyrrole
1,3-dicarbonyl compound
Pyrrole
Heteroaromatic compound
Carboxamide group
Ketone
Secondary carboxylic acid amide
Carboxylic acid derivative
Carbonitrile
Nitrile
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

anilide (CHEBI:8415 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	2.2	ALOGPS
logP	1.87	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-8.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.89 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	75.89 m³·mol⁻¹	ChemAxon
Polarizability	27.7 Å³	ChemAxon
Number of Rings	2	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]+	160.594	30932474
DeepCCS	[M-H]-	158.236	30932474
DeepCCS	[M-2H]-	191.122	30932474
DeepCCS	[M+Na]+	166.688	30932474
AllCCS	[M+H]+	161.1	32859911
AllCCS	[M+H-H2O]+	157.3	32859911
AllCCS	[M+NH4]+	164.7	32859911
AllCCS	[M+Na]+	165.7	32859911
AllCCS	[M-H]-	163.8	32859911
AllCCS	[M+Na-2H]-	163.5	32859911
AllCCS	[M+HCOO]-	163.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prinomide	CN1C=CC=C1C(=O)C(C#N)C(=O)NC1=CC=CC=C1	3169.3	Standard polar	33892256
Prinomide	CN1C=CC=C1C(=O)C(C#N)C(=O)NC1=CC=CC=C1	2411.4	Standard non polar	33892256
Prinomide	CN1C=CC=C1C(=O)C(C#N)C(=O)NC1=CC=CC=C1	2258.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Prinomide,1TMS,isomer #1	CN1C=CC=C1C(=O)C(C#N)C(=O)N(C1=CC=CC=C1)[Si](C)(C)C	2201.9	Semi standard non polar	33892256
Prinomide,1TMS,isomer #1	CN1C=CC=C1C(=O)C(C#N)C(=O)N(C1=CC=CC=C1)[Si](C)(C)C	2326.3	Standard non polar	33892256
Prinomide,1TMS,isomer #1	CN1C=CC=C1C(=O)C(C#N)C(=O)N(C1=CC=CC=C1)[Si](C)(C)C	3082.0	Standard polar	33892256
Prinomide,1TBDMS,isomer #1	CN1C=CC=C1C(=O)C(C#N)C(=O)N(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2411.0	Semi standard non polar	33892256
Prinomide,1TBDMS,isomer #1	CN1C=CC=C1C(=O)C(C#N)C(=O)N(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2512.1	Standard non polar	33892256
Prinomide,1TBDMS,isomer #1	CN1C=CC=C1C(=O)C(C#N)C(=O)N(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3151.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Prinomide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0596-9510000000-a83bc21ba3aa3b6d62a7	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prinomide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

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	Not Specified	Not Specified	Normal	31557052	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

54416

KEGG Compound ID

C10958

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60352

PDB ID

Not Available

ChEBI ID

8415

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Prinomide (HMDB0256775)

MOL for HMDB0256775 (Prinomide)

3D MOL for HMDB0256775 (Prinomide)

3D SDF for HMDB0256775 (Prinomide)

3D-SDF for HMDB0256775 (Prinomide)

PDB for HMDB0256775 (Prinomide)

3D PDB for HMDB0256775 (Prinomide)

SMILES for HMDB0256775 (Prinomide)

INCHI for HMDB0256775 (Prinomide)

Structure for HMDB0256775 (Prinomide)

3D Structure for HMDB0256775 (Prinomide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra