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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:42:28 UTC

Update Date

2021-09-26 22:52:22 UTC

HMDB ID

HMDB0244557

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)-

Description

2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)-, also known as 3-hydroxy-N-(2-methylphenyl)naphthalene-2-carboximidate or 3-hydroxy-4'-nitro-2-naphthanilide chloroacetate, belongs to the class of organic compounds known as naphthalene-2-carboxanilides. These are naphthalene-2-carboxamides, where the carboxamide group is substituted with an aniline. Based on a literature review very few articles have been published on 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)-. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2-naphthalenecarboxamide, 3-hydroxy-n-(2-methylphenyl)- is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- 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

HMDB0244557
     RDKit          3D
2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)-
 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.4273    1.9551    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8020    0.5185    0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0957    0.1200   -0.2033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4629   -1.2086   -0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4751   -2.1109    0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1702   -1.7140    0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8053   -0.3818    0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4690    0.0150    0.6404 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4582   -0.3718   -0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7373   -1.2503   -1.0904 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9306    0.0026    0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9199   -0.5285   -0.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2553   -0.2551   -0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1985   -0.8003   -1.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5426   -0.5217   -1.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9148    0.3321   -0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9849    0.8813    0.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6361    0.5976    0.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    1.1328    1.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3175    0.8510    1.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4312    1.4212    2.0889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4304    2.0050   -0.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1920    2.5531   -0.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2923    2.3582    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8880    0.8299   -0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4770   -1.5155   -0.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7485   -3.1641    0.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3863   -2.4366    0.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9473   -0.9296   -2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6353   -1.2088   -1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8637   -1.4683   -2.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2493   -0.9668   -1.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9715    0.5509   -0.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2714    1.5536    1.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9846    1.8029    2.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5336    1.3519    2.1700 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
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
  7  2  1  0
 20 11  1  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
 10 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 19 35  1  0
 21 36  1  0
M  END


  Mrv1652306031607582D          

 21 23  0  0  0  0            999 V2000
    5.7158   -0.0000    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  2  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 12  1  1  0  0  0  0
 12  6  2  0  0  0  0
 13  7  2  0  0  0  0
 13 10  1  0  0  0  0
 14  8  2  0  0  0  0
 14 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 10  2  0  0  0  0
 16  9  2  0  0  0  0
 16 12  1  0  0  0  0
 17 11  2  0  0  0  0
 17 15  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  4  0  0  0
 19 18  2  0  0  0  0
 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244557

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=CC=C1N=C(O)C1=CC2=CC=CC=C2C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H15NO2/c1-12-6-2-5-9-16(12)19-18(21)15-10-13-7-3-4-8-14(13)11-17(15)20/h2-11,20H,1H3,(H,19,21)

> <INCHI_KEY>
FBLAHUMENIHUGG-UHFFFAOYSA-N

> <FORMULA>
C18H15NO2

> <MOLECULAR_WEIGHT>
277.323

> <EXACT_MASS>
277.110278727

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
30.58129848890852

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-N-(2-methylphenyl)naphthalene-2-carboximidic acid

> <ALOGPS_LOGP>
3.95

> <JCHEM_LOGP>
5.641920116333334

> <ALOGPS_LOGS>
-4.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.362386435625455

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.0332529598727085

> <JCHEM_PKA_STRONGEST_BASIC>
1.0027064459960224

> <JCHEM_POLAR_SURFACE_AREA>
52.82000000000001

> <JCHEM_REFRACTIVITY>
85.8189

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.21e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-N-(2-methylphenyl)naphthalene-2-carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0244557
     RDKit          3D
2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)-
 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.4273    1.9551    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8020    0.5185    0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0957    0.1200   -0.2033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4629   -1.2086   -0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4751   -2.1109    0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1702   -1.7140    0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8053   -0.3818    0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4690    0.0150    0.6404 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4582   -0.3718   -0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7373   -1.2503   -1.0904 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9306    0.0026    0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9199   -0.5285   -0.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2553   -0.2551   -0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1985   -0.8003   -1.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5426   -0.5217   -1.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9148    0.3321   -0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9849    0.8813    0.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6361    0.5976    0.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    1.1328    1.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3175    0.8510    1.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4312    1.4212    2.0889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4304    2.0050   -0.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1920    2.5531   -0.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2923    2.3582    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8880    0.8299   -0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4770   -1.5155   -0.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7485   -3.1641    0.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3863   -2.4366    0.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9473   -0.9296   -2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6353   -1.2088   -1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8637   -1.4683   -2.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2493   -0.9668   -1.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9715    0.5509   -0.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2714    1.5536    1.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9846    1.8029    2.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5336    1.3519    2.1700 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
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
  7  2  1  0
 20 11  1  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
 10 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 19 35  1  0
 21 36  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       8.002   1.540   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2    5    6                                                       
CONECT    3    4    7                                                       
CONECT    4    3    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   12                                                       
CONECT    7    3   13                                                       
CONECT    8    4   14                                                       
CONECT    9    5   16                                                       
CONECT   10   13   15                                                       
CONECT   11   14   17                                                       
CONECT   12    1    6   16                                                  
CONECT   13    7   10   14                                                  
CONECT   14    8   11   13                                                  
CONECT   15   10   17   18                                                  
CONECT   16    9   12   19                                                  
CONECT   17   11   15   20                                                  
CONECT   18   15   19   21                                                  
CONECT   19   16   18                                                       
CONECT   20   17                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0244557
HETATM    1  C1  UNL     1      -3.427   1.955   0.003  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.802   0.519   0.056  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.096   0.120  -0.203  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.463  -1.209  -0.159  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.475  -2.111   0.155  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.170  -1.714   0.416  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.805  -0.382   0.372  1.00  0.00           C  
HETATM    8  N1  UNL     1      -1.469   0.015   0.640  1.00  0.00           N  
HETATM    9  C8  UNL     1      -0.458  -0.372  -0.026  1.00  0.00           C  
HETATM   10  O1  UNL     1      -0.737  -1.250  -1.090  1.00  0.00           O  
HETATM   11  C9  UNL     1       0.931   0.003   0.205  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.920  -0.529  -0.641  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.255  -0.255  -0.529  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.198  -0.800  -1.384  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.543  -0.522  -1.267  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.915   0.332  -0.251  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.985   0.881   0.608  1.00  0.00           C  
HETATM   18  C16 UNL     1       3.636   0.598   0.485  1.00  0.00           C  
HETATM   19  C17 UNL     1       2.691   1.133   1.328  1.00  0.00           C  
HETATM   20  C18 UNL     1       1.318   0.851   1.212  1.00  0.00           C  
HETATM   21  O2  UNL     1       0.431   1.421   2.089  1.00  0.00           O  
HETATM   22  H1  UNL     1      -2.430   2.005  -0.512  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.192   2.553  -0.529  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.292   2.358   1.024  1.00  0.00           H  
HETATM   25  H4  UNL     1      -5.888   0.830  -0.454  1.00  0.00           H  
HETATM   26  H5  UNL     1      -6.477  -1.515  -0.363  1.00  0.00           H  
HETATM   27  H6  UNL     1      -4.748  -3.164   0.194  1.00  0.00           H  
HETATM   28  H7  UNL     1      -2.386  -2.437   0.666  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.947  -0.930  -2.008  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.635  -1.209  -1.453  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.864  -1.468  -2.172  1.00  0.00           H  
HETATM   32  H11 UNL     1       6.249  -0.967  -1.954  1.00  0.00           H  
HETATM   33  H12 UNL     1       6.972   0.551  -0.158  1.00  0.00           H  
HETATM   34  H13 UNL     1       5.271   1.554   1.409  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.985   1.803   2.125  1.00  0.00           H  
HETATM   36  H15 UNL     1      -0.534   1.352   2.170  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3    7
CONECT    3    4   25
CONECT    4    5    5   26
CONECT    5    6   27
CONECT    6    7    7   28
CONECT    7    8
CONECT    8    9    9
CONECT    9   10   11
CONECT   10   29
CONECT   11   12   12   20
CONECT   12   13   30
CONECT   13   14   14   18
CONECT   14   15   31
CONECT   15   16   16   32
CONECT   16   17   33
CONECT   17   18   18   34
CONECT   18   19
CONECT   19   20   20   35
CONECT   20   21
CONECT   21   36
END

HMDB0244557
     RDKit          3D
2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)-
 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.4273    1.9551    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8020    0.5185    0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0957    0.1200   -0.2033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4629   -1.2086   -0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4751   -2.1109    0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1702   -1.7140    0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8053   -0.3818    0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4690    0.0150    0.6404 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4582   -0.3718   -0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7373   -1.2503   -1.0904 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9306    0.0026    0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9199   -0.5285   -0.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2553   -0.2551   -0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1985   -0.8003   -1.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5426   -0.5217   -1.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9148    0.3321   -0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9849    0.8813    0.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6361    0.5976    0.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    1.1328    1.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3175    0.8510    1.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4312    1.4212    2.0889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4304    2.0050   -0.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1920    2.5531   -0.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2923    2.3582    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8880    0.8299   -0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4770   -1.5155   -0.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7485   -3.1641    0.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3863   -2.4366    0.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9473   -0.9296   -2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6353   -1.2088   -1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8637   -1.4683   -2.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2493   -0.9668   -1.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9715    0.5509   -0.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2714    1.5536    1.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9846    1.8029    2.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5336    1.3519    2.1700 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
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
  7  2  1  0
 20 11  1  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
 10 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 19 35  1  0
 21 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Hydroxy-N-(2-methylphenyl)naphthalene-2-carboximidate	HMDB
3-Hydroxy-4'-nitro-2-naphthanilide chloroacetate	HMDB
Naphthol as-D	HMDB

Chemical Formula

C₁₈H₁₅NO₂

Average Molecular Weight

277.323

Monoisotopic Molecular Weight

277.110278727

IUPAC Name

3-hydroxy-N-(2-methylphenyl)naphthalene-2-carboximidic acid

Traditional Name

3-hydroxy-N-(2-methylphenyl)naphthalene-2-carboximidic acid

CAS Registry Number

Not Available

SMILES

CC1=CC=CC=C1N=C(O)C1=CC2=CC=CC=C2C=C1O

InChI Identifier

InChI=1S/C18H15NO2/c1-12-6-2-5-9-16(12)19-18(21)15-10-13-7-3-4-8-14(13)11-17(15)20/h2-11,20H,1H3,(H,19,21)

InChI Key

FBLAHUMENIHUGG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalene-2-carboxanilides. These are naphthalene-2-carboxamides, where the carboxamide group is substituted with an aniline.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthalenecarboxylic acids and derivatives

Direct Parent

Naphthalene-2-carboxanilides

Alternative Parents

Substituents

Naphthalene-2-carboxanilide
Aromatic anilide
2-naphthol
Salicylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Toluene
Monocyclic benzene moiety
Vinylogous acid
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.95	ALOGPS
logP	5.64	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	5.03	ChemAxon
pKa (Strongest Basic)	1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.82 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	85.82 m³·mol⁻¹	ChemAxon
Polarizability	30.58 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	158.824	30932474
DeepCCS	[M-H]-	156.466	30932474
DeepCCS	[M-2H]-	189.68	30932474
DeepCCS	[M+Na]+	164.917	30932474
AllCCS	[M+H]+	165.3	32859911
AllCCS	[M+H-H2O]+	161.5	32859911
AllCCS	[M+NH4]+	168.7	32859911
AllCCS	[M+Na]+	169.7	32859911
AllCCS	[M-H]-	169.3	32859911
AllCCS	[M+Na-2H]-	168.4	32859911
AllCCS	[M+HCOO]-	167.5	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.	7.04 minutes	32390414
Predicted by Siyang on May 30, 2022	17.6759 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.08 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2631.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	535.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	215.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	303.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	252.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	790.6 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	942.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	89.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1372.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	691.0 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	1797.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	483.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	568.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	485.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	363.6 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	60.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)-	CC1=CC=CC=C1N=C(O)C1=CC2=CC=CC=C2C=C1O	3642.2	Standard polar	33892256
2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)-	CC1=CC=CC=C1N=C(O)C1=CC2=CC=CC=C2C=C1O	2516.5	Standard non polar	33892256
2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)-	CC1=CC=CC=C1N=C(O)C1=CC2=CC=CC=C2C=C1O	2677.9	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 - 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-0960000000-c3808a8080ea38bc6f00	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- 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 - 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- 10V, Positive-QTOF	splash10-004i-0290000000-4c297348b3b82482ffdf	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- 20V, Positive-QTOF	splash10-00di-2930000000-ad88b2935919aafc0749	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- 40V, Positive-QTOF	splash10-0a6u-9800000000-867571575f922fe76544	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- 10V, Negative-QTOF	splash10-004i-0190000000-1b1b35ba829ebba07143	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- 20V, Negative-QTOF	splash10-004i-0590000000-e0f2789ee7bf04d61982	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- 40V, Negative-QTOF	splash10-0k96-0900000000-3d577c525364cfd4d763	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- 10V, Positive-QTOF	splash10-004i-0390000000-c007e652bbbcce06edee	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- 20V, Positive-QTOF	splash10-00di-0900000000-e40ca6d01f03a5791414	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- 40V, Positive-QTOF	splash10-054o-4900000000-5e8b04819bc36b87fcde	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- 10V, Negative-QTOF	splash10-004i-0090000000-876c7dacd17e4ee1d5f7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- 20V, Negative-QTOF	splash10-002f-0960000000-c98ed4d1681a9dd82cb2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- 40V, Negative-QTOF	splash10-00kf-0900000000-c8d1964ec6328b7dbdc8	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

60605

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

67273

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 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- (HMDB0244557)

MOL for HMDB0244557 (2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)-)

3D MOL for HMDB0244557 (2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)-)

3D SDF for HMDB0244557 (2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)-)

3D-SDF for HMDB0244557 (2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)-)

PDB for HMDB0244557 (2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)-)

3D PDB for HMDB0244557 (2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)-)

SMILES for HMDB0244557 (2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)-)

INCHI for HMDB0244557 (2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)-)

Structure for HMDB0244557 (2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)-)

3D Structure for HMDB0244557 (2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)-)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra