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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:16:49 UTC

Update Date

2021-09-26 22:55:10 UTC

HMDB ID

HMDB0246247

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N,N'-Bis(salicylidene)-1,2-phenylenediamine

Description

N,N'-Bis(salicylidene)-1,2-phenylenediamine, also known as salophen, belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position. Based on a literature review a significant number of articles have been published on N,N'-Bis(salicylidene)-1,2-phenylenediamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). N,n'-bis(salicylidene)-1,2-phenylenediamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N,N'-Bis(salicylidene)-1,2-phenylenediamine 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

HMDB0246247
     RDKit          3D
N,N'-Bis(salicylidene)-1,2-phenylenediamine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.4532   -1.0128    1.2004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9062    0.1907    0.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5787    1.3756    1.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0617    2.5938    0.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8778    2.5967    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2064    1.4492   -0.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7240    0.2021    0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0189   -1.0226   -0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9047   -0.9237   -0.9195 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953   -2.1200   -1.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643   -3.2989   -1.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1659   -4.4356   -1.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2114   -4.4494   -1.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8752   -3.2666   -1.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1814   -2.1228   -1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8598   -0.8884   -1.1200 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7161   -0.2633   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3704    0.9848    0.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    1.6147    1.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8077    2.8042    1.8043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6620    3.4065    0.8974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8648    2.7791   -0.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2283    1.5892   -0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4147    0.9325   -1.8287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1251   -1.9264    1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5188    1.3114    1.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5688    3.5167    1.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4670    3.5586   -0.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2755    1.4418   -0.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4062   -1.9816    0.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9453   -3.3066   -1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7158   -5.3540   -2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7490   -5.3490   -2.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9585   -3.2267   -1.7973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488   -0.7018    0.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4939    1.1320    2.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6222    3.2619    2.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1738    4.3383    1.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5372    3.2284   -1.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0317    1.3420   -2.5169 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  3
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
  7  2  1  0
 15 10  1  0
 23 18  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  8 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 17 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
 22 39  1  0
 24 40  1  0
M  END

  Mrv1652309112101172D          

 24 26  0  0  0  0            999 V2000
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 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
  9 14  1  0  0  0  0
 15 14  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
  4 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246247

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=CC=C1C=NC1=CC=CC=C1N=CC1=CC=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H16N2O2/c23-19-11-5-1-7-15(19)13-21-17-9-3-4-10-18(17)22-14-16-8-2-6-12-20(16)24/h1-14,23-24H

> <INCHI_KEY>
HXFYGSOGECBSOY-UHFFFAOYSA-N

> <FORMULA>
C20H16N2O2

> <MOLECULAR_WEIGHT>
316.36

> <EXACT_MASS>
316.121177763

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
34.57157281415678

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{[(2-{[(2-hydroxyphenyl)methylidene]amino}phenyl)imino]methyl}phenol

> <ALOGPS_LOGP>
4.31

> <JCHEM_LOGP>
5.114636998

> <ALOGPS_LOGS>
-5.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.63052028175571

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.028460141804533

> <JCHEM_PKA_STRONGEST_BASIC>
0.584689139644049

> <JCHEM_POLAR_SURFACE_AREA>
65.18

> <JCHEM_REFRACTIVITY>
100.67900000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(2-{[(2-hydroxyphenyl)methylidene]amino}phenyl)imino]methyl}phenol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0246247
     RDKit          3D
N,N'-Bis(salicylidene)-1,2-phenylenediamine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.4532   -1.0128    1.2004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9062    0.1907    0.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5787    1.3756    1.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0617    2.5938    0.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8778    2.5967    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2064    1.4492   -0.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7240    0.2021    0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0189   -1.0226   -0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9047   -0.9237   -0.9195 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953   -2.1200   -1.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643   -3.2989   -1.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1659   -4.4356   -1.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2114   -4.4494   -1.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8752   -3.2666   -1.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1814   -2.1228   -1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8598   -0.8884   -1.1200 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7161   -0.2633   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3704    0.9848    0.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    1.6147    1.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8077    2.8042    1.8043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6620    3.4065    0.8974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8648    2.7791   -0.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2283    1.5892   -0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4147    0.9325   -1.8287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1251   -1.9264    1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5188    1.3114    1.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5688    3.5167    1.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4670    3.5586   -0.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2755    1.4418   -0.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4062   -1.9816    0.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9453   -3.3066   -1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7158   -5.3540   -2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7490   -5.3490   -2.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9585   -3.2267   -1.7973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488   -0.7018    0.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4939    1.1320    2.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6222    3.2619    2.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1738    4.3383    1.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5372    3.2284   -1.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0317    1.3420   -2.5169 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  3
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
  7  2  1  0
 15 10  1  0
 23 18  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  8 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 17 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
 22 39  1  0
 24 40  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      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      10.669  -0.000   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      13.337   1.540   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.672   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.672  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.338  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.004  -0.000   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.670  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   24                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17   23                                                  
CONECT   23   22                                                            
CONECT   24    4                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0246247
HETATM    1  O1  UNL     1      -4.453  -1.013   1.200  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.906   0.191   0.809  1.00  0.00           C  
HETATM    3  C2  UNL     1      -4.579   1.376   1.146  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.062   2.594   0.772  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.878   2.597   0.066  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.206   1.449  -0.272  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.724   0.202   0.104  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.019  -1.023  -0.250  1.00  0.00           C  
HETATM    9  N1  UNL     1      -0.905  -0.924  -0.920  1.00  0.00           N  
HETATM   10  C8  UNL     1      -0.195  -2.120  -1.277  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.864  -3.299  -1.526  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.166  -4.436  -1.868  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.211  -4.449  -1.976  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.875  -3.267  -1.725  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.181  -2.123  -1.382  1.00  0.00           C  
HETATM   16  N2  UNL     1       1.860  -0.888  -1.120  1.00  0.00           N  
HETATM   17  C14 UNL     1       1.716  -0.263  -0.023  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.370   0.985   0.305  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.173   1.615   1.514  1.00  0.00           C  
HETATM   20  C17 UNL     1       2.808   2.804   1.804  1.00  0.00           C  
HETATM   21  C18 UNL     1       3.662   3.407   0.897  1.00  0.00           C  
HETATM   22  C19 UNL     1       3.865   2.779  -0.319  1.00  0.00           C  
HETATM   23  C20 UNL     1       3.228   1.589  -0.607  1.00  0.00           C  
HETATM   24  O2  UNL     1       3.415   0.932  -1.829  1.00  0.00           O  
HETATM   25  H1  UNL     1      -4.125  -1.926   1.054  1.00  0.00           H  
HETATM   26  H2  UNL     1      -5.519   1.311   1.710  1.00  0.00           H  
HETATM   27  H3  UNL     1      -4.569   3.517   1.024  1.00  0.00           H  
HETATM   28  H4  UNL     1      -2.467   3.559  -0.231  1.00  0.00           H  
HETATM   29  H5  UNL     1      -1.275   1.442  -0.826  1.00  0.00           H  
HETATM   30  H6  UNL     1      -2.406  -1.982   0.033  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.945  -3.307  -1.447  1.00  0.00           H  
HETATM   32  H8  UNL     1      -0.716  -5.354  -2.060  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.749  -5.349  -2.245  1.00  0.00           H  
HETATM   34  H10 UNL     1       2.959  -3.227  -1.797  1.00  0.00           H  
HETATM   35  H11 UNL     1       1.049  -0.702   0.727  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.494   1.132   2.230  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.622   3.262   2.766  1.00  0.00           H  
HETATM   38  H14 UNL     1       4.174   4.338   1.096  1.00  0.00           H  
HETATM   39  H15 UNL     1       4.537   3.228  -1.065  1.00  0.00           H  
HETATM   40  H16 UNL     1       4.032   1.342  -2.517  1.00  0.00           H  
CONECT    1    2   25
CONECT    2    3    3    7
CONECT    3    4   26
CONECT    4    5    5   27
CONECT    5    6   28
CONECT    6    7    7   29
CONECT    7    8
CONECT    8    9    9   30
CONECT    9   10
CONECT   10   11   11   15
CONECT   11   12   31
CONECT   12   13   13   32
CONECT   13   14   33
CONECT   14   15   15   34
CONECT   15   16
CONECT   16   17   17
CONECT   17   18   35
CONECT   18   19   19   23
CONECT   19   20   36
CONECT   20   21   21   37
CONECT   21   22   38
CONECT   22   23   23   39
CONECT   23   24
CONECT   24   40
END

HMDB0246247
     RDKit          3D
N,N'-Bis(salicylidene)-1,2-phenylenediamine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.4532   -1.0128    1.2004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9062    0.1907    0.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5787    1.3756    1.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0617    2.5938    0.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8778    2.5967    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2064    1.4492   -0.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7240    0.2021    0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0189   -1.0226   -0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9047   -0.9237   -0.9195 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953   -2.1200   -1.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643   -3.2989   -1.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1659   -4.4356   -1.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2114   -4.4494   -1.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8752   -3.2666   -1.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1814   -2.1228   -1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8598   -0.8884   -1.1200 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7161   -0.2633   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3704    0.9848    0.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    1.6147    1.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8077    2.8042    1.8043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6620    3.4065    0.8974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8648    2.7791   -0.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2283    1.5892   -0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4147    0.9325   -1.8287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1251   -1.9264    1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5188    1.3114    1.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5688    3.5167    1.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4670    3.5586   -0.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2755    1.4418   -0.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4062   -1.9816    0.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9453   -3.3066   -1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7158   -5.3540   -2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7490   -5.3490   -2.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9585   -3.2267   -1.7973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488   -0.7018    0.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4939    1.1320    2.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6222    3.2619    2.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1738    4.3383    1.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5372    3.2284   -1.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0317    1.3420   -2.5169 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  3
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
  7  2  1  0
 15 10  1  0
 23 18  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  8 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 17 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
 22 39  1  0
 24 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Salophen	HMDB

Chemical Formula

C₂₀H₁₆N₂O₂

Average Molecular Weight

316.36

Monoisotopic Molecular Weight

316.121177763

IUPAC Name

2-{[(2-{[(2-hydroxyphenyl)methylidene]amino}phenyl)imino]methyl}phenol

Traditional Name

2-{[(2-{[(2-hydroxyphenyl)methylidene]amino}phenyl)imino]methyl}phenol

CAS Registry Number

Not Available

SMILES

OC1=CC=CC=C1C=NC1=CC=CC=C1N=CC1=CC=CC=C1O

InChI Identifier

InChI=1S/C20H16N2O2/c23-19-11-5-1-7-15(19)13-21-17-9-3-4-10-18(17)22-14-16-8-2-6-12-20(16)24/h1-14,23-24H

InChI Key

HXFYGSOGECBSOY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-4-unsubstituted benzenoids

Direct Parent

1-hydroxy-4-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Shiff base
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Aldimine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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	4.31	ALOGPS
logP	5.11	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	8.03	ChemAxon
pKa (Strongest Basic)	0.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.18 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	100.68 m³·mol⁻¹	ChemAxon
Polarizability	34.57 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	165.596	30932474
DeepCCS	[M-H]-	163.238	30932474
DeepCCS	[M-2H]-	196.666	30932474
DeepCCS	[M+Na]+	171.893	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N,N'-Bis(salicylidene)-1,2-phenylenediamine	OC1=CC=CC=C1C=NC1=CC=CC=C1N=CC1=CC=CC=C1O	3648.3	Standard polar	33892256
N,N'-Bis(salicylidene)-1,2-phenylenediamine	OC1=CC=CC=C1C=NC1=CC=CC=C1N=CC1=CC=CC=C1O	3252.0	Standard non polar	33892256
N,N'-Bis(salicylidene)-1,2-phenylenediamine	OC1=CC=CC=C1C=NC1=CC=CC=C1N=CC1=CC=CC=C1O	3232.3	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,N'-Bis(salicylidene)-1,2-phenylenediamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2962000000-e3c5d2b1d4319357db40	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N,N'-Bis(salicylidene)-1,2-phenylenediamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N,N'-Bis(salicylidene)-1,2-phenylenediamine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N,N'-Bis(salicylidene)-1,2-phenylenediamine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N,N'-Bis(salicylidene)-1,2-phenylenediamine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N,N'-Bis(salicylidene)-1,2-phenylenediamine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	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,N'-Bis(salicylidene)-1,2-phenylenediamine 10V, Positive-QTOF	splash10-014i-0009000000-46baf6ca560d45e09626	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N'-Bis(salicylidene)-1,2-phenylenediamine 20V, Positive-QTOF	splash10-02ta-2395000000-d1709f339efd08e3a9d7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N'-Bis(salicylidene)-1,2-phenylenediamine 40V, Positive-QTOF	splash10-004l-9730000000-af45b765a6643d003594	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N'-Bis(salicylidene)-1,2-phenylenediamine 10V, Negative-QTOF	splash10-014i-0409000000-7bdabb0d6ba265fdfa0b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N'-Bis(salicylidene)-1,2-phenylenediamine 20V, Negative-QTOF	splash10-0avi-0193000000-2fb071e481fab3237893	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N'-Bis(salicylidene)-1,2-phenylenediamine 40V, Negative-QTOF	splash10-01oy-3291000000-820e00d3ebd5b3566ed0	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

28534389

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

221227

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

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 N,N'-Bis(salicylidene)-1,2-phenylenediamine (HMDB0246247)

MOL for HMDB0246247 (N,N'-Bis(salicylidene)-1,2-phenylenediamine)

3D MOL for HMDB0246247 (N,N'-Bis(salicylidene)-1,2-phenylenediamine)

3D SDF for HMDB0246247 (N,N'-Bis(salicylidene)-1,2-phenylenediamine)

3D-SDF for HMDB0246247 (N,N'-Bis(salicylidene)-1,2-phenylenediamine)

PDB for HMDB0246247 (N,N'-Bis(salicylidene)-1,2-phenylenediamine)

3D PDB for HMDB0246247 (N,N'-Bis(salicylidene)-1,2-phenylenediamine)

SMILES for HMDB0246247 (N,N'-Bis(salicylidene)-1,2-phenylenediamine)

INCHI for HMDB0246247 (N,N'-Bis(salicylidene)-1,2-phenylenediamine)

Structure for HMDB0246247 (N,N'-Bis(salicylidene)-1,2-phenylenediamine)

3D Structure for HMDB0246247 (N,N'-Bis(salicylidene)-1,2-phenylenediamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra