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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:22:13 UTC

Update Date

2021-09-26 23:12:44 UTC

HMDB ID

HMDB0256787

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Procainamide 4-hydroxylamine

Description

Procainamide 4-hydroxylamine, also known as para-hydroxylamine procainamide or PAHA, belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring. Procainamide 4-hydroxylamine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Procainamide 4-hydroxylamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Procainamide 4-hydroxylamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Procainamide 4-hydroxylamine 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

HMDB0256787
     RDKit          3D
Procainamide 4-hydroxylamine
 39 39  0  0  0  0  0  0  0  0999 V2000
   -4.9395   -0.1043   -1.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7474   -1.0223   -0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6305   -0.4248   -0.2546 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8417   -0.2394    1.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9319   -1.5156    1.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4166    0.8702   -0.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2865    1.6510   -0.2676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0214    0.9542   -0.3660 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1868    1.5021    0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027    2.6436    0.6729 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4651    0.8487    0.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5887    1.5062    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8227    0.8989    0.4542 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9763   -0.3731   -0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2618   -0.9922   -0.1113 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4030   -2.2241   -0.6049 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792   -1.0486   -0.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6479   -0.4151   -0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8017    0.6350   -1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0756    0.5047   -0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8703   -0.6564   -1.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9749   -2.0385   -0.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4018   -1.1301   -2.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6857    0.4314    1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9216    0.2826    1.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7851   -2.1518    1.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -1.2366    2.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9691   -2.0723    1.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3633    1.4536   -0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3482    0.8126   -1.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1752    2.5618   -0.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4947    2.0752    0.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0209    0.0142   -0.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4802    2.5214    0.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7056    1.4298    0.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1195   -0.5052    0.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3070   -2.4341   -0.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9778   -2.0555   -0.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7959   -0.9572   -0.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  2  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
M  END

  Mrv1652309112119222D          

 18 18  0  0  0  0            999 V2000
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256787

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(CC)CCNC(=O)C1=CC=C(NO)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H21N3O2/c1-3-16(4-2)10-9-14-13(17)11-5-7-12(15-18)8-6-11/h5-8,15,18H,3-4,9-10H2,1-2H3,(H,14,17)

> <INCHI_KEY>
JBFULHOJGOVPTK-UHFFFAOYSA-N

> <FORMULA>
C13H21N3O2

> <MOLECULAR_WEIGHT>
251.33

> <EXACT_MASS>
251.163376928

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.87768797507764

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[2-(diethylamino)ethyl]-4-(hydroxyamino)benzamide

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
1.288092516333333

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.854910819006687

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.868201569975694

> <JCHEM_PKA_STRONGEST_BASIC>
9.044353174130606

> <JCHEM_POLAR_SURFACE_AREA>
64.60000000000001

> <JCHEM_REFRACTIVITY>
74.5366

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
PAHA

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256787
     RDKit          3D
Procainamide 4-hydroxylamine
 39 39  0  0  0  0  0  0  0  0999 V2000
   -4.9395   -0.1043   -1.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7474   -1.0223   -0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6305   -0.4248   -0.2546 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8417   -0.2394    1.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9319   -1.5156    1.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4166    0.8702   -0.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2865    1.6510   -0.2676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0214    0.9542   -0.3660 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1868    1.5021    0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027    2.6436    0.6729 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4651    0.8487    0.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5887    1.5062    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8227    0.8989    0.4542 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9763   -0.3731   -0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2618   -0.9922   -0.1113 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4030   -2.2241   -0.6049 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792   -1.0486   -0.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6479   -0.4151   -0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8017    0.6350   -1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0756    0.5047   -0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8703   -0.6564   -1.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9749   -2.0385   -0.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4018   -1.1301   -2.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6857    0.4314    1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9216    0.2826    1.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7851   -2.1518    1.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -1.2366    2.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9691   -2.0723    1.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3633    1.4536   -0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3482    0.8126   -1.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1752    2.5618   -0.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4947    2.0752    0.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0209    0.0142   -0.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4802    2.5214    0.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7056    1.4298    0.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1195   -0.5052    0.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3070   -2.4341   -0.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9778   -2.0555   -0.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7959   -0.9572   -0.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  2  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  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      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -4.001  -2.310   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0256787
HETATM    1  C1  UNL     1      -4.939  -0.104  -1.012  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.747  -1.022  -0.954  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.630  -0.425  -0.255  1.00  0.00           N  
HETATM    4  C3  UNL     1      -2.842  -0.239   1.136  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.932  -1.516   1.929  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.417   0.870  -0.865  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.287   1.651  -0.268  1.00  0.00           C  
HETATM    8  N2  UNL     1      -0.021   0.954  -0.366  1.00  0.00           N  
HETATM    9  C7  UNL     1       1.187   1.502   0.132  1.00  0.00           C  
HETATM   10  O1  UNL     1       1.103   2.644   0.673  1.00  0.00           O  
HETATM   11  C8  UNL     1       2.465   0.849   0.058  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.589   1.506   0.513  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.823   0.899   0.454  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.976  -0.373  -0.056  1.00  0.00           C  
HETATM   15  N3  UNL     1       6.262  -0.992  -0.111  1.00  0.00           N  
HETATM   16  O2  UNL     1       6.403  -2.224  -0.605  1.00  0.00           O  
HETATM   17  C12 UNL     1       3.879  -1.049  -0.514  1.00  0.00           C  
HETATM   18  C13 UNL     1       2.648  -0.415  -0.444  1.00  0.00           C  
HETATM   19  H1  UNL     1      -4.802   0.635  -1.846  1.00  0.00           H  
HETATM   20  H2  UNL     1      -5.076   0.505  -0.096  1.00  0.00           H  
HETATM   21  H3  UNL     1      -5.870  -0.656  -1.236  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.975  -2.039  -0.620  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.402  -1.130  -2.026  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.686   0.431   1.396  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.922   0.283   1.535  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.785  -2.152   1.663  1.00  0.00           H  
HETATM   27  H9  UNL     1      -3.058  -1.237   2.995  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.969  -2.072   1.851  1.00  0.00           H  
HETATM   29  H11 UNL     1      -3.363   1.454  -0.659  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.348   0.813  -1.972  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.175   2.562  -0.937  1.00  0.00           H  
HETATM   32  H14 UNL     1      -1.495   2.075   0.725  1.00  0.00           H  
HETATM   33  H15 UNL     1       0.021   0.014  -0.817  1.00  0.00           H  
HETATM   34  H16 UNL     1       3.480   2.521   0.922  1.00  0.00           H  
HETATM   35  H17 UNL     1       5.706   1.430   0.818  1.00  0.00           H  
HETATM   36  H18 UNL     1       7.120  -0.505   0.229  1.00  0.00           H  
HETATM   37  H19 UNL     1       7.307  -2.434  -0.913  1.00  0.00           H  
HETATM   38  H20 UNL     1       3.978  -2.055  -0.922  1.00  0.00           H  
HETATM   39  H21 UNL     1       1.796  -0.957  -0.807  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4    6
CONECT    4    5   24   25
CONECT    5   26   27   28
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9   33
CONECT    9   10   10   11
CONECT   11   12   12   18
CONECT   12   13   34
CONECT   13   14   14   35
CONECT   14   15   17
CONECT   15   16   36
CONECT   16   37
CONECT   17   18   18   38
CONECT   18   39
END

HMDB0256787
     RDKit          3D
Procainamide 4-hydroxylamine
 39 39  0  0  0  0  0  0  0  0999 V2000
   -4.9395   -0.1043   -1.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7474   -1.0223   -0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6305   -0.4248   -0.2546 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8417   -0.2394    1.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9319   -1.5156    1.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4166    0.8702   -0.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2865    1.6510   -0.2676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0214    0.9542   -0.3660 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1868    1.5021    0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027    2.6436    0.6729 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4651    0.8487    0.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5887    1.5062    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8227    0.8989    0.4542 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9763   -0.3731   -0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2618   -0.9922   -0.1113 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4030   -2.2241   -0.6049 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792   -1.0486   -0.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6479   -0.4151   -0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8017    0.6350   -1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0756    0.5047   -0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8703   -0.6564   -1.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9749   -2.0385   -0.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4018   -1.1301   -2.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6857    0.4314    1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9216    0.2826    1.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7851   -2.1518    1.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -1.2366    2.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9691   -2.0723    1.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3633    1.4536   -0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3482    0.8126   -1.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1752    2.5618   -0.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4947    2.0752    0.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0209    0.0142   -0.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4802    2.5214    0.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7056    1.4298    0.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1195   -0.5052    0.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3070   -2.4341   -0.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9778   -2.0555   -0.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7959   -0.9572   -0.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  2  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxylamino-N,N-diethylaminoethylbenzamide	ChEBI
PAHA	ChEBI
Para-hydroxylamine procainamide	ChEBI
Procainamide hydroxylamine	ChEBI

Chemical Formula

C₁₃H₂₁N₃O₂

Average Molecular Weight

251.33

Monoisotopic Molecular Weight

251.163376928

IUPAC Name

N-[2-(diethylamino)ethyl]-4-(hydroxyamino)benzamide

Traditional Name

PAHA

CAS Registry Number

Not Available

SMILES

CCN(CC)CCNC(=O)C1=CC=C(NO)C=C1

InChI Identifier

InChI=1S/C13H21N3O2/c1-3-16(4-2)10-9-14-13(17)11-5-7-12(15-18)8-6-11/h5-8,15,18H,3-4,9-10H2,1-2H3,(H,14,17)

InChI Key

JBFULHOJGOVPTK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzamides

Alternative Parents

Substituents

Benzamide
N-phenylhydroxylamine
1-hydroxylamino, 2-unsubstituted benzenoid
Benzoyl
Arylhydroxamate
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
N-organohydroxylamine
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

hydroxylamines (CHEBI:60726 )
benzamides (CHEBI:60726 )

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	1.58	ALOGPS
logP	1.29	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	13.87	ChemAxon
pKa (Strongest Basic)	9.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	64.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	74.54 m³·mol⁻¹	ChemAxon
Polarizability	28.88 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
DeepCCS	[M+H]+	158.663	30932474
DeepCCS	[M-H]-	156.305	30932474
DeepCCS	[M-2H]-	189.254	30932474
DeepCCS	[M+Na]+	164.756	30932474
AllCCS	[M+H]+	159.9	32859911
AllCCS	[M+H-H2O]+	156.5	32859911
AllCCS	[M+NH4]+	163.1	32859911
AllCCS	[M+Na]+	164.1	32859911
AllCCS	[M-H]-	162.5	32859911
AllCCS	[M+Na-2H]-	163.1	32859911
AllCCS	[M+HCOO]-	163.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Procainamide 4-hydroxylamine	CCN(CC)CCNC(=O)C1=CC=C(NO)C=C1	3364.1	Standard polar	33892256
Procainamide 4-hydroxylamine	CCN(CC)CCNC(=O)C1=CC=C(NO)C=C1	2455.4	Standard non polar	33892256
Procainamide 4-hydroxylamine	CCN(CC)CCNC(=O)C1=CC=C(NO)C=C1	2535.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Procainamide 4-hydroxylamine,1TMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(NO)C=C1)[Si](C)(C)C	2449.4	Semi standard non polar	33892256
Procainamide 4-hydroxylamine,1TMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(NO)C=C1)[Si](C)(C)C	2543.8	Standard non polar	33892256
Procainamide 4-hydroxylamine,1TMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(NO)C=C1)[Si](C)(C)C	3064.8	Standard polar	33892256
Procainamide 4-hydroxylamine,1TMS,isomer #2	CCN(CC)CCNC(=O)C1=CC=C(N(O)[Si](C)(C)C)C=C1	2514.6	Semi standard non polar	33892256
Procainamide 4-hydroxylamine,1TMS,isomer #2	CCN(CC)CCNC(=O)C1=CC=C(N(O)[Si](C)(C)C)C=C1	2467.5	Standard non polar	33892256
Procainamide 4-hydroxylamine,1TMS,isomer #2	CCN(CC)CCNC(=O)C1=CC=C(N(O)[Si](C)(C)C)C=C1	3065.7	Standard polar	33892256
Procainamide 4-hydroxylamine,2TMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(N(O)[Si](C)(C)C)C=C1)[Si](C)(C)C	2391.6	Semi standard non polar	33892256
Procainamide 4-hydroxylamine,2TMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(N(O)[Si](C)(C)C)C=C1)[Si](C)(C)C	2460.2	Standard non polar	33892256
Procainamide 4-hydroxylamine,2TMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(N(O)[Si](C)(C)C)C=C1)[Si](C)(C)C	2804.5	Standard polar	33892256
Procainamide 4-hydroxylamine,1TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(NO)C=C1)[Si](C)(C)C(C)(C)C	2726.2	Semi standard non polar	33892256
Procainamide 4-hydroxylamine,1TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(NO)C=C1)[Si](C)(C)C(C)(C)C	2758.2	Standard non polar	33892256
Procainamide 4-hydroxylamine,1TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(NO)C=C1)[Si](C)(C)C(C)(C)C	3095.1	Standard polar	33892256
Procainamide 4-hydroxylamine,1TBDMS,isomer #2	CCN(CC)CCNC(=O)C1=CC=C(N(O)[Si](C)(C)C(C)(C)C)C=C1	2743.7	Semi standard non polar	33892256
Procainamide 4-hydroxylamine,1TBDMS,isomer #2	CCN(CC)CCNC(=O)C1=CC=C(N(O)[Si](C)(C)C(C)(C)C)C=C1	2641.6	Standard non polar	33892256
Procainamide 4-hydroxylamine,1TBDMS,isomer #2	CCN(CC)CCNC(=O)C1=CC=C(N(O)[Si](C)(C)C(C)(C)C)C=C1	3090.2	Standard polar	33892256
Procainamide 4-hydroxylamine,2TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(N(O)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2913.1	Semi standard non polar	33892256
Procainamide 4-hydroxylamine,2TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(N(O)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2827.0	Standard non polar	33892256
Procainamide 4-hydroxylamine,2TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(N(O)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2970.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Procainamide 4-hydroxylamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-9710000000-f7008046cd43c23f1fae	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Procainamide 4-hydroxylamine 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

111723

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

125600

PDB ID

Not Available

ChEBI ID

60726

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 Procainamide 4-hydroxylamine (HMDB0256787)

MOL for HMDB0256787 (Procainamide 4-hydroxylamine)

3D MOL for HMDB0256787 (Procainamide 4-hydroxylamine)

3D SDF for HMDB0256787 (Procainamide 4-hydroxylamine)

3D-SDF for HMDB0256787 (Procainamide 4-hydroxylamine)

PDB for HMDB0256787 (Procainamide 4-hydroxylamine)

3D PDB for HMDB0256787 (Procainamide 4-hydroxylamine)

SMILES for HMDB0256787 (Procainamide 4-hydroxylamine)

INCHI for HMDB0256787 (Procainamide 4-hydroxylamine)

Structure for HMDB0256787 (Procainamide 4-hydroxylamine)

3D Structure for HMDB0256787 (Procainamide 4-hydroxylamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra