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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015377

Secondary Accession Numbers

HMDB15377

Metabolite Identification

Common Name

Isocarboxazid

Description

Isocarboxazid is only found in individuals that have used or taken this drug. It is an MAO inhibitor that is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in the treatment of panic disorder and the phobic disorders. (From AMA, Drug Evaluations Annual, 1994, p311). Isocarboxazid works by irreversibly blocking the action of a chemical substance known as monoamine oxidase (MAO) in the nervous system. MAO subtypes A and B are involved in the metabolism of serotonin and catecholamine neurotransmitters such as epinephrine, norepinephrine, and dopamine. Isocarboxazid, as a nonselective MAO inhibitor, binds irreversibly to monoamine oxidase–A (MAO-A) and monoamine oxidase–B (MAO-B). The reduced MAO activity results in an increased concentration of these neurotransmitters in storage sites throughout the central nervous system (CNS) and sympathetic nervous system. This increased availability of one or more monoamines is the basis for the antidepressant activity of MAO inhibitors.

Structure

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

HMDB0015377
     RDKit          3D
Isocarboxazid
 30 31  0  0  0  0  0  0  0  0999 V2000
    6.5294    0.2650    0.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1261    0.2459   -0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0043   -0.2198    0.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9033   -0.0596   -0.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5146   -0.4169    0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2618   -0.8829    1.2310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4639   -0.2524   -0.8554 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8315   -0.6027   -0.4735 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6616    0.5937   -0.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0059    0.2329   -0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2807    0.3766    1.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5197    0.0547    1.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4744   -0.4116    0.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2354   -0.5690   -0.6284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9590   -0.2301   -1.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3889    0.4826   -1.3687 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697    0.6535   -1.2732 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6064    0.8560    1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1671    0.6568   -0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8920   -0.7569    0.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9924   -0.6338    1.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6394    0.1161   -1.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8688   -0.8276    0.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2248    1.4449   -0.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6326    0.9142   -1.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5119    0.7510    1.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6910    0.1845    2.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4632   -0.6678    1.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0171   -0.9398   -1.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7819   -0.3574   -2.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  4 16  2  0
 16 17  1  0
 17  2  1  0
 15 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
M  END

1247
  Mrv0541 02231215212D          

 17 18  0  0  0  0            999 V2000
    3.3809    2.7761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.2690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.5560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.2690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1260    1.9915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -3.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4609    1.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060    2.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6909    3.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1 15  1  0  0  0  0
  2 11  2  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  4 11  1  0  0  0  0
  5 10  2  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
  8 12  1  0  0  0  0
  9 13  2  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 12 16  2  0  0  0  0
 13 16  1  0  0  0  0
 14 15  2  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015377

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(=NO1)C(=O)NNCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H13N3O2/c1-9-7-11(15-17-9)12(16)14-13-8-10-5-3-2-4-6-10/h2-7,13H,8H2,1H3,(H,14,16)

> <INCHI_KEY>
XKFPYPQQHFEXRZ-UHFFFAOYSA-N

> <FORMULA>
C12H13N3O2

> <MOLECULAR_WEIGHT>
231.2505

> <EXACT_MASS>
231.100776675

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.510960717633893

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N'-benzyl-5-methyl-1,2-oxazole-3-carbohydrazide

> <ALOGPS_LOGP>
1.19

> <JCHEM_LOGP>
1.4255166486666668

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.021473156034329

> <JCHEM_PKA_STRONGEST_BASIC>
3.123385867616713

> <JCHEM_POLAR_SURFACE_AREA>
67.16

> <JCHEM_REFRACTIVITY>
74.78030000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isocarboxazid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015377
     RDKit          3D
Isocarboxazid
 30 31  0  0  0  0  0  0  0  0999 V2000
    6.5294    0.2650    0.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1261    0.2459   -0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0043   -0.2198    0.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9033   -0.0596   -0.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5146   -0.4169    0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2618   -0.8829    1.2310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4639   -0.2524   -0.8554 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8315   -0.6027   -0.4735 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6616    0.5937   -0.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0059    0.2329   -0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2807    0.3766    1.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5197    0.0547    1.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4744   -0.4116    0.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2354   -0.5690   -0.6284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9590   -0.2301   -1.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3889    0.4826   -1.3687 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697    0.6535   -1.2732 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6064    0.8560    1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1671    0.6568   -0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8920   -0.7569    0.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9924   -0.6338    1.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6394    0.1161   -1.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8688   -0.8276    0.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2248    1.4449   -0.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6326    0.9142   -1.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5119    0.7510    1.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6910    0.1845    2.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4632   -0.6678    1.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0171   -0.9398   -1.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7819   -0.3574   -2.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  4 16  2  0
 16 17  1  0
 17  2  1  0
 15 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1247                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       6.311   5.182   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415   0.502   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.747  -1.038   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       5.747   0.502   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       5.835   3.717   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.414  -1.808   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414  -3.348   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.747  -4.118   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.080  -4.118   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081   2.812   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   1.272   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.747  -5.658   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080  -5.658   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.327   3.717   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.851   5.182   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414  -6.428   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.756   6.428   0.000  0.00  0.00           C+0
CONECT    1    5   15                                                       
CONECT    2   11                                                            
CONECT    3    4    6                                                       
CONECT    4    3   11                                                       
CONECT    5    1   10                                                       
CONECT    6    3    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7   12                                                       
CONECT    9    7   13                                                       
CONECT   10    5   11   14                                                  
CONECT   11    2    4   10                                                  
CONECT   12    8   16                                                       
CONECT   13    9   16                                                       
CONECT   14   10   15                                                       
CONECT   15    1   14   17                                                  
CONECT   16   12   13                                                       
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0015377
HETATM    1  C1  UNL     1       6.529   0.265   0.413  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.126   0.246  -0.100  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.004  -0.220   0.584  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.903  -0.060  -0.245  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.515  -0.417   0.081  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.262  -0.883   1.231  1.00  0.00           O  
HETATM    7  N1  UNL     1       0.464  -0.252  -0.855  1.00  0.00           N  
HETATM    8  N2  UNL     1      -0.832  -0.603  -0.473  1.00  0.00           N  
HETATM    9  C6  UNL     1      -1.662   0.594  -0.687  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.006   0.233  -0.214  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.281   0.377   1.123  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.520   0.055   1.601  1.00  0.00           C  
HETATM   13  C10 UNL     1      -5.474  -0.412   0.720  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.235  -0.569  -0.628  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.959  -0.230  -1.079  1.00  0.00           C  
HETATM   16  N3  UNL     1       3.389   0.483  -1.369  1.00  0.00           N  
HETATM   17  O2  UNL     1       4.670   0.654  -1.273  1.00  0.00           O  
HETATM   18  H1  UNL     1       6.606   0.856   1.335  1.00  0.00           H  
HETATM   19  H2  UNL     1       7.167   0.657  -0.405  1.00  0.00           H  
HETATM   20  H3  UNL     1       6.892  -0.757   0.636  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.992  -0.634   1.584  1.00  0.00           H  
HETATM   22  H5  UNL     1       0.639   0.116  -1.820  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.869  -0.828   0.525  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.225   1.445  -0.117  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.633   0.914  -1.752  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.512   0.751   1.819  1.00  0.00           H  
HETATM   27  H10 UNL     1      -4.691   0.184   2.658  1.00  0.00           H  
HETATM   28  H11 UNL     1      -6.463  -0.668   1.107  1.00  0.00           H  
HETATM   29  H12 UNL     1      -6.017  -0.940  -1.274  1.00  0.00           H  
HETATM   30  H13 UNL     1      -3.782  -0.357  -2.136  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   17
CONECT    3    4   21
CONECT    4    5   16   16
CONECT    5    6    6    7
CONECT    7    8   22
CONECT    8    9   23
CONECT    9   10   24   25
CONECT   10   11   11   15
CONECT   11   12   26
CONECT   12   13   13   27
CONECT   13   14   28
CONECT   14   15   15   29
CONECT   15   30
CONECT   16   17
END

HMDB0015377
     RDKit          3D
Isocarboxazid
 30 31  0  0  0  0  0  0  0  0999 V2000
    6.5294    0.2650    0.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1261    0.2459   -0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0043   -0.2198    0.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9033   -0.0596   -0.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5146   -0.4169    0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2618   -0.8829    1.2310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4639   -0.2524   -0.8554 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8315   -0.6027   -0.4735 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6616    0.5937   -0.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0059    0.2329   -0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2807    0.3766    1.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5197    0.0547    1.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4744   -0.4116    0.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2354   -0.5690   -0.6284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9590   -0.2301   -1.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3889    0.4826   -1.3687 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697    0.6535   -1.2732 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6064    0.8560    1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1671    0.6568   -0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8920   -0.7569    0.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9924   -0.6338    1.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6394    0.1161   -1.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8688   -0.8276    0.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2248    1.4449   -0.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6326    0.9142   -1.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5119    0.7510    1.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6910    0.1845    2.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4632   -0.6678    1.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0171   -0.9398   -1.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7819   -0.3574   -2.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  4 16  2  0
 16 17  1  0
 17  2  1  0
 15 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Marplan	Kegg
Isocarbonazid	HMDB
Isocarbossazide	HMDB
Isocarboxazide	HMDB
Isocarboxyzid	HMDB

Chemical Formula

C₁₂H₁₃N₃O₂

Average Molecular Weight

231.2505

Monoisotopic Molecular Weight

231.100776675

IUPAC Name

N'-benzyl-5-methyl-1,2-oxazole-3-carbohydrazide

Traditional Name

isocarboxazid

CAS Registry Number

59-63-2

SMILES

CC1=CC(=NO1)C(=O)NNCC1=CC=CC=C1

InChI Identifier

InChI=1S/C12H13N3O2/c1-9-7-11(15-17-9)12(16)14-13-8-10-5-3-2-4-6-10/h2-7,13H,8H2,1H3,(H,14,16)

InChI Key

XKFPYPQQHFEXRZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Azole
Isoxazole
Heteroaromatic compound
Carboxylic acid hydrazide
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Oxacycle
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015377)
Extracellular (HMDB: HMDB0015377)

Source

Exogenous

Exogenous (HMDB: HMDB0015377)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	105 - 106 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.22 g/L	Not Available
LogP	2.4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	152.1	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	1.19	ALOGPS
logP	1.43	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.02	ChemAxon
pKa (Strongest Basic)	3.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.16 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.78 m³·mol⁻¹	ChemAxon
Polarizability	24.51 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
DarkChem	[M+H]+	153.982	31661259
DarkChem	[M-H]-	155.381	31661259
DeepCCS	[M+H]+	153.926	30932474
DeepCCS	[M-H]-	151.568	30932474
DeepCCS	[M-2H]-	184.641	30932474
DeepCCS	[M+Na]+	160.019	30932474
AllCCS	[M+H]+	153.2	32859911
AllCCS	[M+H-H2O]+	149.2	32859911
AllCCS	[M+NH4]+	157.0	32859911
AllCCS	[M+Na]+	158.1	32859911
AllCCS	[M-H]-	155.9	32859911
AllCCS	[M+Na-2H]-	155.9	32859911
AllCCS	[M+HCOO]-	156.0	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.	4.3 minutes	32390414
Predicted by Siyang on May 30, 2022	13.3507 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.59 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1874.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	395.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	163.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	211.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	89.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	439.2 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	684.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	114.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1151.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	431.4 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	1357.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	346.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	366.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	374.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	308.5 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	59.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isocarboxazid	CC1=CC(=NO1)C(=O)NNCC1=CC=CC=C1	2516.3	Standard polar	33892256
Isocarboxazid	CC1=CC(=NO1)C(=O)NNCC1=CC=CC=C1	2066.3	Standard non polar	33892256
Isocarboxazid	CC1=CC(=NO1)C(=O)NNCC1=CC=CC=C1	2066.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isocarboxazid,1TMS,isomer #1	CC1=CC(C(=O)N(NCC2=CC=CC=C2)[Si](C)(C)C)=NO1	2189.9	Semi standard non polar	33892256
Isocarboxazid,1TMS,isomer #1	CC1=CC(C(=O)N(NCC2=CC=CC=C2)[Si](C)(C)C)=NO1	2109.0	Standard non polar	33892256
Isocarboxazid,1TMS,isomer #1	CC1=CC(C(=O)N(NCC2=CC=CC=C2)[Si](C)(C)C)=NO1	2892.4	Standard polar	33892256
Isocarboxazid,1TMS,isomer #2	CC1=CC(C(=O)NN(CC2=CC=CC=C2)[Si](C)(C)C)=NO1	2133.1	Semi standard non polar	33892256
Isocarboxazid,1TMS,isomer #2	CC1=CC(C(=O)NN(CC2=CC=CC=C2)[Si](C)(C)C)=NO1	2061.4	Standard non polar	33892256
Isocarboxazid,1TMS,isomer #2	CC1=CC(C(=O)NN(CC2=CC=CC=C2)[Si](C)(C)C)=NO1	3052.7	Standard polar	33892256
Isocarboxazid,2TMS,isomer #1	CC1=CC(C(=O)N(N(CC2=CC=CC=C2)[Si](C)(C)C)[Si](C)(C)C)=NO1	2169.5	Semi standard non polar	33892256
Isocarboxazid,2TMS,isomer #1	CC1=CC(C(=O)N(N(CC2=CC=CC=C2)[Si](C)(C)C)[Si](C)(C)C)=NO1	2155.8	Standard non polar	33892256
Isocarboxazid,2TMS,isomer #1	CC1=CC(C(=O)N(N(CC2=CC=CC=C2)[Si](C)(C)C)[Si](C)(C)C)=NO1	2688.3	Standard polar	33892256
Isocarboxazid,1TBDMS,isomer #1	CC1=CC(C(=O)N(NCC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)=NO1	2451.4	Semi standard non polar	33892256
Isocarboxazid,1TBDMS,isomer #1	CC1=CC(C(=O)N(NCC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)=NO1	2310.3	Standard non polar	33892256
Isocarboxazid,1TBDMS,isomer #1	CC1=CC(C(=O)N(NCC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)=NO1	2976.0	Standard polar	33892256
Isocarboxazid,1TBDMS,isomer #2	CC1=CC(C(=O)NN(CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)=NO1	2386.7	Semi standard non polar	33892256
Isocarboxazid,1TBDMS,isomer #2	CC1=CC(C(=O)NN(CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)=NO1	2261.5	Standard non polar	33892256
Isocarboxazid,1TBDMS,isomer #2	CC1=CC(C(=O)NN(CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)=NO1	3146.8	Standard polar	33892256
Isocarboxazid,2TBDMS,isomer #1	CC1=CC(C(=O)N(N(CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NO1	2674.2	Semi standard non polar	33892256
Isocarboxazid,2TBDMS,isomer #1	CC1=CC(C(=O)N(N(CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NO1	2518.1	Standard non polar	33892256
Isocarboxazid,2TBDMS,isomer #1	CC1=CC(C(=O)N(N(CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NO1	2895.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Isocarboxazid EI-B (Non-derivatized)	splash10-0006-9600000000-952a7c1093fe532d1df3	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isocarboxazid EI-B (Non-derivatized)	splash10-0006-9600000000-952a7c1093fe532d1df3	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isocarboxazid GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9510000000-c11f3aaa62df1be7ea3f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isocarboxazid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isocarboxazid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9500000000-6ab30f52fc69889b3fa2	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isocarboxazid LC-ESI-qTof , Positive-QTOF	splash10-0006-9210100010-78b2f412502a142509e6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isocarboxazid , positive-QTOF	splash10-0006-9210100010-78b2f412502a142509e6	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocarboxazid 10V, Positive-QTOF	splash10-001i-3290000000-9801781c24b97ecc0817	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocarboxazid 20V, Positive-QTOF	splash10-0006-9350000000-d8f9ca354f060f4330e2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocarboxazid 40V, Positive-QTOF	splash10-0006-9100000000-6cedb1354fdeece131f6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocarboxazid 10V, Negative-QTOF	splash10-001i-1690000000-07a8545573baa300826f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocarboxazid 20V, Negative-QTOF	splash10-001l-9640000000-077985063287a38f7095	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocarboxazid 40V, Negative-QTOF	splash10-0kx0-9300000000-a6c0764f23b7adf2144e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocarboxazid 10V, Positive-QTOF	splash10-001l-6390000000-911dc29e6ed1ee470433	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocarboxazid 20V, Positive-QTOF	splash10-0006-9100000000-4896c74c701f3ec4b2fd	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocarboxazid 40V, Positive-QTOF	splash10-0006-9200000000-cc7b99641fc7414fb559	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocarboxazid 10V, Negative-QTOF	splash10-001i-0090000000-b203703a00eee615a207	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocarboxazid 20V, Negative-QTOF	splash10-001l-9110000000-fc267c475e490b4f9f3c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocarboxazid 40V, Negative-QTOF	splash10-000x-9100000000-b1b63bbca6e5cb19e8b8	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01247	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01247	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01247

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3628

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isocarboxazid

METLIN ID

Not Available

PubChem Compound

3759

PDB ID

Not Available

ChEBI ID

775119

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

Kennedy SH, Piran N, Warsh JJ, Prendergast P, Mainprize E, Whynot C, Garfinkel PE: A trial of isocarboxazid in the treatment of bulimia nervosa. J Clin Psychopharmacol. 1988 Dec;8(6):391-6. [PubMed:3069879 ]

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

References

Mason ST: Chronic administration of type A monoamine oxidase inhibitors increases duration of thiopentone anaesthesia in the rat. Physiol Behav. 1985 Aug;35(2):201-3. [PubMed:4070383 ]
Kettler R, Da Prada M, Burkard WP: Comparison of monoamine oxidase-A inhibition by moclobemide in vitro and ex vivo in rats. Acta Psychiatr Scand Suppl. 1990;360:101-2. [PubMed:2248058 ]

Enzyme Details

2. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Thase ME, Trivedi MH, Rush AJ: MAOIs in the contemporary treatment of depression. Neuropsychopharmacology. 1995 May;12(3):185-219. [PubMed:7612154 ]
Kettler R, Da Prada M, Burkard WP: Comparison of monoamine oxidase-A inhibition by moclobemide in vitro and ex vivo in rats. Acta Psychiatr Scand Suppl. 1990;360:101-2. [PubMed:2248058 ]

Showing metabocard for Isocarboxazid (HMDB0015377)

MOL for HMDB0015377 (Isocarboxazid)

3D MOL for HMDB0015377 (Isocarboxazid)

3D SDF for HMDB0015377 (Isocarboxazid)

3D-SDF for HMDB0015377 (Isocarboxazid)

PDB for HMDB0015377 (Isocarboxazid)

3D PDB for HMDB0015377 (Isocarboxazid)

SMILES for HMDB0015377 (Isocarboxazid)

INCHI for HMDB0015377 (Isocarboxazid)

Structure for HMDB0015377 (Isocarboxazid)

3D Structure for HMDB0015377 (Isocarboxazid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References