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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:11:37 UTC

Update Date

2019-07-23 07:15:32 UTC

HMDB ID

HMDB0060996

Secondary Accession Numbers

HMDB60996

Metabolite Identification

Common Name

N-Acetyl-3-hydroxyprocainamide

Description

N-Acetyl-3-hydroxyprocainamide, also known as NA-3-HP, belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated. N-Acetyl-3-hydroxyprocainamide is a very strong basic compound (based on its pKa).

Structure

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

HMDB0060996
     RDKit          3D
N-Acetyl-3-hydroxyprocainamide
 44 44  0  0  0  0  0  0  0  0999 V2000
   -5.9239    0.6144   -1.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4635    0.5265   -0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0686   -0.7360   -0.4212 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5637   -1.1340    0.8295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0060   -1.4402    0.9711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6313   -0.8768   -0.4780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9000    0.0326    0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764   -0.1965    0.3169 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3435    0.5740    0.9379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1223    1.6039    1.7301 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8052    0.3739    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6647    1.2081    1.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0269    1.0433    1.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5232    0.0156    0.6245 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9083   -0.2356    0.4880 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6470    0.4537   -0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0969    0.0744   -0.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1369    1.4819   -1.0601 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6483   -0.8318   -0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1273   -1.8649   -0.8438 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2944   -0.6463    0.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1019    1.4136   -2.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5178    0.9256   -0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2003   -0.3265   -1.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8897    0.7289   -1.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1715    1.3677   -0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9682   -2.0238    1.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3384   -0.3104    1.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6211   -0.6188    1.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1065   -2.2690    1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4721   -1.8633    0.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3098   -1.9210   -0.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2484   -0.6706   -1.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0758    1.0960    0.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1879   -0.2384    1.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1044    2.5442    1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2607    2.0118    2.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7344    1.6728    1.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4395   -0.0782    0.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2194   -0.8978   -0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6798    0.8510   -0.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167    2.3166   -0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4702   -2.4548   -1.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6264   -1.2958   -0.4781 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  2  3
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 14 19  1  0
 19 20  1  0
 19 21  2  0
 21 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 10 36  1  0
 12 37  1  0
 13 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 20 43  1  0
 21 44  1  0
M  END


  Mrv0541 07091309112D          

 21 21  0  0  0  0            999 V2000
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.1250    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  7  6  2  0  0  0  0
  9  8  1  0  0  0  0
 11  3  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  2  0  0  0  0
 13  7  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  2  0  0  0  0
 15 12  1  0  0  0  0
 16  8  1  4  0  0  0
 16 15  2  0  0  0  0
 17 11  2  0  0  0  0
 17 13  1  4  0  0  0
 18  4  1  0  0  0  0
 18  5  1  0  0  0  0
 18  9  1  0  0  0  0
 19 11  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060996

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(CC)CCN=C(O)C1=CC(O)=C(C=C1)N=C(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C15H23N3O3/c1-4-18(5-2)9-8-16-15(21)12-6-7-13(14(20)10-12)17-11(3)19/h6-7,10,20H,4-5,8-9H2,1-3H3,(H,16,21)(H,17,19)

> <INCHI_KEY>
REELIONXYPAEGO-UHFFFAOYSA-N

> <FORMULA>
C15H23N3O3

> <MOLECULAR_WEIGHT>
293.3614

> <EXACT_MASS>
293.173941617

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
33.35797305701169

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[2-(diethylamino)ethyl]-3-hydroxy-4-[(1-hydroxyethylidene)amino]benzene-1-carboximidic acid

> <ALOGPS_LOGP>
1.64

> <JCHEM_LOGP>
0.8156913663388844

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
8.152455140899589

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.670241301808488

> <JCHEM_PKA_STRONGEST_BASIC>
9.946270139620534

> <JCHEM_POLAR_SURFACE_AREA>
88.65

> <JCHEM_REFRACTIVITY>
85.6701

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[2-(diethylamino)ethyl]-3-hydroxy-4-[(1-hydroxyethylidene)amino]benzenecarboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060996
     RDKit          3D
N-Acetyl-3-hydroxyprocainamide
 44 44  0  0  0  0  0  0  0  0999 V2000
   -5.9239    0.6144   -1.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4635    0.5265   -0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0686   -0.7360   -0.4212 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5637   -1.1340    0.8295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0060   -1.4402    0.9711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6313   -0.8768   -0.4780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9000    0.0326    0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764   -0.1965    0.3169 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3435    0.5740    0.9379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1223    1.6039    1.7301 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8052    0.3739    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6647    1.2081    1.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0269    1.0433    1.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5232    0.0156    0.6245 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9083   -0.2356    0.4880 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6470    0.4537   -0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0969    0.0744   -0.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1369    1.4819   -1.0601 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6483   -0.8318   -0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1273   -1.8649   -0.8438 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2944   -0.6463    0.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1019    1.4136   -2.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5178    0.9256   -0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2003   -0.3265   -1.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8897    0.7289   -1.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1715    1.3677   -0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9682   -2.0238    1.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3384   -0.3104    1.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6211   -0.6188    1.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1065   -2.2690    1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4721   -1.8633    0.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3098   -1.9210   -0.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2484   -0.6706   -1.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0758    1.0960    0.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1879   -0.2384    1.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1044    2.5442    1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2607    2.0118    2.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7344    1.6728    1.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4395   -0.0782    0.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2194   -0.8978   -0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6798    0.8510   -0.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167    2.3166   -0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4702   -2.4548   -1.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6264   -1.2958   -0.4781 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  2  3
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 14 19  1  0
 19 20  1  0
 19 21  2  0
 21 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 10 36  1  0
 12 37  1  0
 13 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 20 43  1  0
 21 44  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  12.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       0.000   7.700   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       6.668  10.010   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -4.001   6.930   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       5.335  12.320   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001  11.550   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3   11                                                            
CONECT    4    1   18                                                       
CONECT    5    2   18                                                       
CONECT    6    7   12                                                       
CONECT    7    6   13                                                       
CONECT    8    9   16                                                       
CONECT    9    8   18                                                       
CONECT   10   12   14                                                       
CONECT   11    3   17   19                                                  
CONECT   12    6   10   15                                                  
CONECT   13    7   14   17                                                  
CONECT   14   10   13   20                                                  
CONECT   15   12   16   21                                                  
CONECT   16    8   15                                                       
CONECT   17   11   13                                                       
CONECT   18    4    5    9                                                  
CONECT   19   11                                                            
CONECT   20   14                                                            
CONECT   21   15                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0060996
HETATM    1  C1  UNL     1      -5.924   0.614  -1.300  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.463   0.526  -0.925  1.00  0.00           C  
HETATM    3  N1  UNL     1      -4.069  -0.736  -0.421  1.00  0.00           N  
HETATM    4  C3  UNL     1      -4.564  -1.134   0.830  1.00  0.00           C  
HETATM    5  C4  UNL     1      -6.006  -1.440   0.971  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.631  -0.877  -0.478  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.900   0.033   0.461  1.00  0.00           C  
HETATM    8  N2  UNL     1      -0.476  -0.196   0.317  1.00  0.00           N  
HETATM    9  C7  UNL     1       0.343   0.574   0.938  1.00  0.00           C  
HETATM   10  O1  UNL     1      -0.122   1.604   1.730  1.00  0.00           O  
HETATM   11  C8  UNL     1       1.805   0.374   0.817  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.665   1.208   1.489  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.027   1.043   1.403  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.523   0.016   0.624  1.00  0.00           C  
HETATM   15  N3  UNL     1       5.908  -0.236   0.488  1.00  0.00           N  
HETATM   16  C12 UNL     1       6.647   0.454  -0.298  1.00  0.00           C  
HETATM   17  C13 UNL     1       8.097   0.074  -0.340  1.00  0.00           C  
HETATM   18  O2  UNL     1       6.137   1.482  -1.060  1.00  0.00           O  
HETATM   19  C14 UNL     1       3.648  -0.832  -0.058  1.00  0.00           C  
HETATM   20  O3  UNL     1       4.127  -1.865  -0.844  1.00  0.00           O  
HETATM   21  C15 UNL     1       2.294  -0.646   0.043  1.00  0.00           C  
HETATM   22  H1  UNL     1      -6.102   1.414  -2.080  1.00  0.00           H  
HETATM   23  H2  UNL     1      -6.518   0.926  -0.431  1.00  0.00           H  
HETATM   24  H3  UNL     1      -6.200  -0.326  -1.772  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.890   0.729  -1.859  1.00  0.00           H  
HETATM   26  H5  UNL     1      -4.171   1.368  -0.234  1.00  0.00           H  
HETATM   27  H6  UNL     1      -3.968  -2.024   1.167  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.338  -0.310   1.574  1.00  0.00           H  
HETATM   29  H8  UNL     1      -6.621  -0.619   1.397  1.00  0.00           H  
HETATM   30  H9  UNL     1      -6.106  -2.269   1.735  1.00  0.00           H  
HETATM   31  H10 UNL     1      -6.472  -1.863   0.053  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.310  -1.921  -0.238  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.248  -0.671  -1.514  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.076   1.096   0.287  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.188  -0.238   1.496  1.00  0.00           H  
HETATM   36  H15 UNL     1      -0.104   2.544   1.313  1.00  0.00           H  
HETATM   37  H16 UNL     1       2.261   2.012   2.096  1.00  0.00           H  
HETATM   38  H17 UNL     1       4.734   1.673   1.911  1.00  0.00           H  
HETATM   39  H18 UNL     1       8.440  -0.078   0.726  1.00  0.00           H  
HETATM   40  H19 UNL     1       8.219  -0.898  -0.836  1.00  0.00           H  
HETATM   41  H20 UNL     1       8.680   0.851  -0.861  1.00  0.00           H  
HETATM   42  H21 UNL     1       5.817   2.317  -0.562  1.00  0.00           H  
HETATM   43  H22 UNL     1       3.470  -2.455  -1.319  1.00  0.00           H  
HETATM   44  H23 UNL     1       1.626  -1.296  -0.478  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4    6
CONECT    4    5   27   28
CONECT    5   29   30   31
CONECT    6    7   32   33
CONECT    7    8   34   35
CONECT    8    9    9
CONECT    9   10   11
CONECT   10   36
CONECT   11   12   12   21
CONECT   12   13   37
CONECT   13   14   14   38
CONECT   14   15   19
CONECT   15   16   16
CONECT   16   17   18
CONECT   17   39   40   41
CONECT   18   42
CONECT   19   20   21   21
CONECT   20   43
CONECT   21   44
END

HMDB0060996
     RDKit          3D
N-Acetyl-3-hydroxyprocainamide
 44 44  0  0  0  0  0  0  0  0999 V2000
   -5.9239    0.6144   -1.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4635    0.5265   -0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0686   -0.7360   -0.4212 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5637   -1.1340    0.8295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0060   -1.4402    0.9711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6313   -0.8768   -0.4780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9000    0.0326    0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764   -0.1965    0.3169 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3435    0.5740    0.9379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1223    1.6039    1.7301 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8052    0.3739    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6647    1.2081    1.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0269    1.0433    1.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5232    0.0156    0.6245 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9083   -0.2356    0.4880 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6470    0.4537   -0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0969    0.0744   -0.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1369    1.4819   -1.0601 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6483   -0.8318   -0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1273   -1.8649   -0.8438 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2944   -0.6463    0.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1019    1.4136   -2.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5178    0.9256   -0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2003   -0.3265   -1.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8897    0.7289   -1.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1715    1.3677   -0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9682   -2.0238    1.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3384   -0.3104    1.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6211   -0.6188    1.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1065   -2.2690    1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4721   -1.8633    0.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3098   -1.9210   -0.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2484   -0.6706   -1.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0758    1.0960    0.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1879   -0.2384    1.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1044    2.5442    1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2607    2.0118    2.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7344    1.6728    1.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4395   -0.0782    0.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2194   -0.8978   -0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6798    0.8510   -0.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167    2.3166   -0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4702   -2.4548   -1.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6264   -1.2958   -0.4781 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  2  3
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 14 19  1  0
 19 20  1  0
 19 21  2  0
 21 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 10 36  1  0
 12 37  1  0
 13 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 20 43  1  0
 21 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
NA-3-HP	HMDB

Chemical Formula

C₁₅H₂₃N₃O₃

Average Molecular Weight

293.3614

Monoisotopic Molecular Weight

293.173941617

IUPAC Name

N-[2-(diethylamino)ethyl]-3-hydroxy-4-[(1-hydroxyethylidene)amino]benzene-1-carboximidic acid

Traditional Name

N-[2-(diethylamino)ethyl]-3-hydroxy-4-[(1-hydroxyethylidene)amino]benzenecarboximidic acid

CAS Registry Number

Not Available

SMILES

CCN(CC)CCN=C(O)C1=CC(O)=C(C=C1)N=C(C)O

InChI Identifier

InChI=1S/C15H23N3O3/c1-4-18(5-2)9-8-16-15(21)12-6-7-13(14(20)10-12)17-11(3)19/h6-7,10,20H,4-5,8-9H2,1-3H3,(H,16,21)(H,17,19)

InChI Key

REELIONXYPAEGO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Acylaminobenzoic acid and derivatives

Alternative Parents

Substituents

Acylaminobenzoic acid or derivatives
Acetanilide
Benzamide
N-acetylarylamine
Anilide
Benzoyl
N-arylamide
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Acetamide
Amino acid or derivatives
Carboxamide group
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Carboxylic acid derivative
Amine
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060996)
Liver (HMDB: HMDB0060996)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060996)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060996)

Cellular substructure

Cytoplasm (HMDB: HMDB0060996)

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
Water Solubility	0.24 g/L	ALOGPS
logP	1.64	ALOGPS
logP	0.82	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.67	ChemAxon
pKa (Strongest Basic)	9.95	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	88.65 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	85.67 m³·mol⁻¹	ChemAxon
Polarizability	33.36 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]+	172.046	31661259
DarkChem	[M-H]-	169.104	31661259
DeepCCS	[M+H]+	173.294	30932474
DeepCCS	[M-H]-	170.936	30932474
DeepCCS	[M-2H]-	203.837	30932474
DeepCCS	[M+Na]+	179.387	30932474
AllCCS	[M+H]+	170.4	32859911
AllCCS	[M+H-H2O]+	167.3	32859911
AllCCS	[M+NH4]+	173.3	32859911
AllCCS	[M+Na]+	174.1	32859911
AllCCS	[M-H]-	172.6	32859911
AllCCS	[M+Na-2H]-	173.1	32859911
AllCCS	[M+HCOO]-	173.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-3-hydroxyprocainamide	CCN(CC)CCN=C(O)C1=CC(O)=C(C=C1)N=C(C)O	3176.5	Standard polar	33892256
N-Acetyl-3-hydroxyprocainamide	CCN(CC)CCN=C(O)C1=CC(O)=C(C=C1)N=C(C)O	2613.1	Standard non polar	33892256
N-Acetyl-3-hydroxyprocainamide	CCN(CC)CCN=C(O)C1=CC(O)=C(C=C1)N=C(C)O	2482.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-3-hydroxyprocainamide,1TMS,isomer #1	CCN(CC)CCN=C(O[Si](C)(C)C)C1=CC=C(N=C(C)O)C(O)=C1	2501.5	Semi standard non polar	33892256
N-Acetyl-3-hydroxyprocainamide,1TMS,isomer #2	CCN(CC)CCN=C(O)C1=CC=C(N=C(C)O)C(O[Si](C)(C)C)=C1	2613.8	Semi standard non polar	33892256
N-Acetyl-3-hydroxyprocainamide,1TMS,isomer #3	CCN(CC)CCN=C(O)C1=CC=C(N=C(C)O[Si](C)(C)C)C(O)=C1	2534.4	Semi standard non polar	33892256
N-Acetyl-3-hydroxyprocainamide,2TMS,isomer #1	CCN(CC)CCN=C(O[Si](C)(C)C)C1=CC=C(N=C(C)O[Si](C)(C)C)C(O)=C1	2450.4	Semi standard non polar	33892256
N-Acetyl-3-hydroxyprocainamide,2TMS,isomer #2	CCN(CC)CCN=C(O[Si](C)(C)C)C1=CC=C(N=C(C)O)C(O[Si](C)(C)C)=C1	2521.9	Semi standard non polar	33892256
N-Acetyl-3-hydroxyprocainamide,2TMS,isomer #3	CCN(CC)CCN=C(O)C1=CC=C(N=C(C)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	2526.6	Semi standard non polar	33892256
N-Acetyl-3-hydroxyprocainamide,3TMS,isomer #1	CCN(CC)CCN=C(O[Si](C)(C)C)C1=CC=C(N=C(C)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	2514.4	Semi standard non polar	33892256
N-Acetyl-3-hydroxyprocainamide,1TBDMS,isomer #1	CCN(CC)CCN=C(O[Si](C)(C)C(C)(C)C)C1=CC=C(N=C(C)O)C(O)=C1	2743.9	Semi standard non polar	33892256
N-Acetyl-3-hydroxyprocainamide,1TBDMS,isomer #2	CCN(CC)CCN=C(O)C1=CC=C(N=C(C)O)C(O[Si](C)(C)C(C)(C)C)=C1	2839.2	Semi standard non polar	33892256
N-Acetyl-3-hydroxyprocainamide,1TBDMS,isomer #3	CCN(CC)CCN=C(O)C1=CC=C(N=C(C)O[Si](C)(C)C(C)(C)C)C(O)=C1	2753.5	Semi standard non polar	33892256
N-Acetyl-3-hydroxyprocainamide,2TBDMS,isomer #1	CCN(CC)CCN=C(O[Si](C)(C)C(C)(C)C)C1=CC=C(N=C(C)O[Si](C)(C)C(C)(C)C)C(O)=C1	2824.9	Semi standard non polar	33892256
N-Acetyl-3-hydroxyprocainamide,2TBDMS,isomer #2	CCN(CC)CCN=C(O[Si](C)(C)C(C)(C)C)C1=CC=C(N=C(C)O)C(O[Si](C)(C)C(C)(C)C)=C1	2924.3	Semi standard non polar	33892256
N-Acetyl-3-hydroxyprocainamide,2TBDMS,isomer #3	CCN(CC)CCN=C(O)C1=CC=C(N=C(C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2947.7	Semi standard non polar	33892256
N-Acetyl-3-hydroxyprocainamide,3TBDMS,isomer #1	CCN(CC)CCN=C(O[Si](C)(C)C(C)(C)C)C1=CC=C(N=C(C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	3046.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-3-hydroxyprocainamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pdr-9330000000-c1c7705773b3a386e376	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-3-hydroxyprocainamide GC-MS (3 TMS) - 70eV, Positive	splash10-000g-7001900000-7469c07ee63b5fc45db6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-3-hydroxyprocainamide 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-3-hydroxyprocainamide 10V, Positive-QTOF	splash10-0udl-0490000000-938ab89c73a1abcc7ddc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-3-hydroxyprocainamide 20V, Positive-QTOF	splash10-0udi-2940000000-e52839289b064cf36b54	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-3-hydroxyprocainamide 40V, Positive-QTOF	splash10-0fk9-8900000000-dfec958177c72657f646	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-3-hydroxyprocainamide 10V, Negative-QTOF	splash10-0006-0090000000-f4a0cfa3cfc4f1aff750	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-3-hydroxyprocainamide 20V, Negative-QTOF	splash10-0udl-4390000000-8d4fee7c7b782815dc08	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-3-hydroxyprocainamide 40V, Negative-QTOF	splash10-0a4l-9400000000-a82c1d03083f65aaeee0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-3-hydroxyprocainamide 10V, Negative-QTOF	splash10-00dj-0390000000-5fb04c1f41b628e3d6bb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-3-hydroxyprocainamide 20V, Negative-QTOF	splash10-0006-1590000000-259ba8f46abd4bb148c1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-3-hydroxyprocainamide 40V, Negative-QTOF	splash10-004i-2900000000-320650ce4c9c210795d4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-3-hydroxyprocainamide 10V, Positive-QTOF	splash10-006x-0190000000-9f073bee4a7812fbf53e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-3-hydroxyprocainamide 20V, Positive-QTOF	splash10-0fmi-0970000000-61b735f46c3fa6e96439	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-3-hydroxyprocainamide 40V, Positive-QTOF	splash10-057r-0900000000-a38c018fe0c0c293b63c	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

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

133158

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

Not Available

Showing metabocard for N-Acetyl-3-hydroxyprocainamide (HMDB0060996)

MOL for HMDB0060996 (N-Acetyl-3-hydroxyprocainamide)

3D MOL for HMDB0060996 (N-Acetyl-3-hydroxyprocainamide)

3D SDF for HMDB0060996 (N-Acetyl-3-hydroxyprocainamide)

3D-SDF for HMDB0060996 (N-Acetyl-3-hydroxyprocainamide)

PDB for HMDB0060996 (N-Acetyl-3-hydroxyprocainamide)

3D PDB for HMDB0060996 (N-Acetyl-3-hydroxyprocainamide)

SMILES for HMDB0060996 (N-Acetyl-3-hydroxyprocainamide)

INCHI for HMDB0060996 (N-Acetyl-3-hydroxyprocainamide)

Structure for HMDB0060996 (N-Acetyl-3-hydroxyprocainamide)

3D Structure for HMDB0060996 (N-Acetyl-3-hydroxyprocainamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra