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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 18:05:59 UTC

Update Date

2021-09-26 23:13:28 UTC

HMDB ID

HMDB0257239

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Riparin III

Description

2,6-dihydroxy-N-[2-(4-methoxyphenyl)ethyl]benzene-1-carboximidic acid belongs to the class of organic compounds known as salicylamides. These are carboxamide derivatives of salicylic acid. Salicylic acid is the ortho-hydroxylated derivative of benzoic acid. Based on a literature review very few articles have been published on 2,6-dihydroxy-N-[2-(4-methoxyphenyl)ethyl]benzene-1-carboximidic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Riparin iii is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Riparin III 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

HMDB0257239
     RDKit          3D
Riparin III
 38 39  0  0  0  0  0  0  0  0999 V2000
   -6.9201   -0.4667   -0.9410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3063   -0.1094    0.2727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9065    0.0209    0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2525    0.3685    1.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8581    0.4961    1.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1208    0.2772    0.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6431    0.4185    0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0396   -0.8643    0.7894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4885   -0.6266    0.8329 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1885   -0.2483   -0.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4966   -0.1365   -1.3757 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6142    0.0381   -0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1437    0.4098   -1.6842 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3982    0.5202   -2.7987 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5226    0.6892   -1.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3228    0.5927   -0.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8001    0.2294    0.4973 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4461   -0.0478    0.6408 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0086   -0.4065    1.9087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -0.0712   -0.7972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1400   -0.1962   -0.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0059   -0.6192   -0.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5111   -1.4234   -1.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7802    0.3521   -1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7836    0.5517    2.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3921    0.7733    2.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588    1.1532    1.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3030    0.7902   -0.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1298   -1.5973   -0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3128   -1.2825    1.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9820   -0.7521    1.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5156    0.4281   -3.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9121    0.9751   -2.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3807    0.8102   -0.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4326    0.1511    1.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6288   -0.4692    2.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2093   -0.2561   -1.7190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6395   -0.4721   -1.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
  6 20  1  0
 20 21  2  0
 21  3  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
M  END

  Mrv1533004241512442D          

 21 22  0  0  0  0            999 V2000
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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 O   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
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  2  0  0  0  0
  3 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0257239

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(CCNC(=O)C2=C(O)C=CC=C2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO4/c1-21-12-7-5-11(6-8-12)9-10-17-16(20)15-13(18)3-2-4-14(15)19/h2-8,18-19H,9-10H2,1H3,(H,17,20)

> <INCHI_KEY>
UNMMJIGEEXRNET-UHFFFAOYSA-N

> <FORMULA>
C16H17NO4

> <MOLECULAR_WEIGHT>
287.315

> <EXACT_MASS>
287.115758031

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
30.285152479787833

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6-dihydroxy-N-[2-(4-methoxyphenyl)ethyl]benzamide

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
3.5958945893333336

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.355648827413416

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.041939955431772

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8674930145399662

> <JCHEM_POLAR_SURFACE_AREA>
78.79

> <JCHEM_REFRACTIVITY>
79.82570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6-dihydroxy-N-[2-(4-methoxyphenyl)ethyl]benzamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0257239
     RDKit          3D
Riparin III
 38 39  0  0  0  0  0  0  0  0999 V2000
   -6.9201   -0.4667   -0.9410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3063   -0.1094    0.2727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9065    0.0209    0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2525    0.3685    1.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8581    0.4961    1.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1208    0.2772    0.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6431    0.4185    0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0396   -0.8643    0.7894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4885   -0.6266    0.8329 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1885   -0.2483   -0.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4966   -0.1365   -1.3757 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6142    0.0381   -0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1437    0.4098   -1.6842 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3982    0.5202   -2.7987 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5226    0.6892   -1.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3228    0.5927   -0.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8001    0.2294    0.4973 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4461   -0.0478    0.6408 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0086   -0.4065    1.9087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -0.0712   -0.7972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1400   -0.1962   -0.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0059   -0.6192   -0.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5111   -1.4234   -1.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7802    0.3521   -1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7836    0.5517    2.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3921    0.7733    2.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588    1.1532    1.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3030    0.7902   -0.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1298   -1.5973   -0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3128   -1.2825    1.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9820   -0.7521    1.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5156    0.4281   -3.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9121    0.9751   -2.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3807    0.8102   -0.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4326    0.1511    1.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6288   -0.4692    2.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2093   -0.2561   -1.7190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6395   -0.4721   -1.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
  6 20  1  0
 20 21  2  0
 21  3  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -3.080   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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.001  -5.390   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18                                                            
CONECT   20    6   21                                                       
CONECT   21   20    3                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0257239
HETATM    1  C1  UNL     1      -6.920  -0.467  -0.941  1.00  0.00           C  
HETATM    2  O1  UNL     1      -6.306  -0.109   0.273  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.907   0.021   0.311  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.253   0.368   1.473  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.858   0.496   1.503  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.121   0.277   0.377  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.643   0.418   0.433  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.040  -0.864   0.789  1.00  0.00           C  
HETATM    9  N1  UNL     1       1.489  -0.627   0.833  1.00  0.00           N  
HETATM   10  C8  UNL     1       2.188  -0.248  -0.305  1.00  0.00           C  
HETATM   11  O2  UNL     1       1.497  -0.137  -1.376  1.00  0.00           O  
HETATM   12  C9  UNL     1       3.614   0.038  -0.434  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.144   0.410  -1.684  1.00  0.00           C  
HETATM   14  O3  UNL     1       3.398   0.520  -2.799  1.00  0.00           O  
HETATM   15  C11 UNL     1       5.523   0.689  -1.817  1.00  0.00           C  
HETATM   16  C12 UNL     1       6.323   0.593  -0.721  1.00  0.00           C  
HETATM   17  C13 UNL     1       5.800   0.229   0.497  1.00  0.00           C  
HETATM   18  C14 UNL     1       4.446  -0.048   0.641  1.00  0.00           C  
HETATM   19  O4  UNL     1       4.009  -0.407   1.909  1.00  0.00           O  
HETATM   20  C15 UNL     1      -2.747  -0.071  -0.797  1.00  0.00           C  
HETATM   21  C16 UNL     1      -4.140  -0.196  -0.817  1.00  0.00           C  
HETATM   22  H1  UNL     1      -8.006  -0.619  -0.777  1.00  0.00           H  
HETATM   23  H2  UNL     1      -6.511  -1.423  -1.355  1.00  0.00           H  
HETATM   24  H3  UNL     1      -6.780   0.352  -1.690  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.784   0.552   2.385  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.392   0.773   2.448  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.359   1.153   1.246  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.303   0.790  -0.543  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.130  -1.597  -0.053  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.313  -1.283   1.741  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.982  -0.752   1.752  1.00  0.00           H  
HETATM   32  H11 UNL     1       2.516   0.428  -3.108  1.00  0.00           H  
HETATM   33  H12 UNL     1       5.912   0.975  -2.794  1.00  0.00           H  
HETATM   34  H13 UNL     1       7.381   0.810  -0.837  1.00  0.00           H  
HETATM   35  H14 UNL     1       6.433   0.151   1.373  1.00  0.00           H  
HETATM   36  H15 UNL     1       4.629  -0.469   2.704  1.00  0.00           H  
HETATM   37  H16 UNL     1      -2.209  -0.256  -1.719  1.00  0.00           H  
HETATM   38  H17 UNL     1      -4.639  -0.472  -1.746  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   25
CONECT    5    6    6   26
CONECT    6    7   20
CONECT    7    8   27   28
CONECT    8    9   29   30
CONECT    9   10   31
CONECT   10   11   11   12
CONECT   12   13   13   18
CONECT   13   14   15
CONECT   14   32
CONECT   15   16   16   33
CONECT   16   17   34
CONECT   17   18   18   35
CONECT   18   19
CONECT   19   36
CONECT   20   21   21   37
CONECT   21   38
END

HMDB0257239
     RDKit          3D
Riparin III
 38 39  0  0  0  0  0  0  0  0999 V2000
   -6.9201   -0.4667   -0.9410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3063   -0.1094    0.2727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9065    0.0209    0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2525    0.3685    1.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8581    0.4961    1.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1208    0.2772    0.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6431    0.4185    0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0396   -0.8643    0.7894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4885   -0.6266    0.8329 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1885   -0.2483   -0.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4966   -0.1365   -1.3757 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6142    0.0381   -0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1437    0.4098   -1.6842 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3982    0.5202   -2.7987 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5226    0.6892   -1.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3228    0.5927   -0.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8001    0.2294    0.4973 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4461   -0.0478    0.6408 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0086   -0.4065    1.9087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -0.0712   -0.7972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1400   -0.1962   -0.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0059   -0.6192   -0.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5111   -1.4234   -1.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7802    0.3521   -1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7836    0.5517    2.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3921    0.7733    2.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588    1.1532    1.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3030    0.7902   -0.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1298   -1.5973   -0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3128   -1.2825    1.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9820   -0.7521    1.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5156    0.4281   -3.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9121    0.9751   -2.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3807    0.8102   -0.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4326    0.1511    1.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6288   -0.4692    2.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2093   -0.2561   -1.7190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6395   -0.4721   -1.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
  6 20  1  0
 20 21  2  0
 21  3  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,6-Dihydroxy-N-[2-(4-methoxyphenyl)ethyl]benzene-1-carboximidate	Generator
O-Methyl-N-(2,6-dihydroxybenzoyl)tyramine	MeSH

Chemical Formula

C₁₆H₁₇NO₄

Average Molecular Weight

287.315

Monoisotopic Molecular Weight

287.115758031

IUPAC Name

2,6-dihydroxy-N-[2-(4-methoxyphenyl)ethyl]benzamide

Traditional Name

2,6-dihydroxy-N-[2-(4-methoxyphenyl)ethyl]benzamide

CAS Registry Number

Not Available

SMILES

COC1=CC=C(CCNC(=O)C2=C(O)C=CC=C2O)C=C1

InChI Identifier

InChI=1S/C16H17NO4/c1-21-12-7-5-11(6-8-12)9-10-17-16(20)15-13(18)3-2-4-14(15)19/h2-8,18-19H,9-10H2,1H3,(H,17,20)

InChI Key

UNMMJIGEEXRNET-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as salicylamides. These are carboxamide derivatives of salicylic acid. Salicylic acid is the ortho-hydroxylated derivative of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Salicylamides

Alternative Parents

Substituents

Salicylamide
Benzamide
Phenoxy compound
Anisole
Benzoyl
Methoxybenzene
Resorcinol
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Ether
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
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	2.01	ALOGPS
logP	3.6	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.04	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	78.79 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.83 m³·mol⁻¹	ChemAxon
Polarizability	30.29 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
DeepCCS	[M+H]+	169.27	30932474
DeepCCS	[M-H]-	166.912	30932474
DeepCCS	[M-2H]-	199.798	30932474
DeepCCS	[M+Na]+	175.363	30932474
AllCCS	[M+H]+	168.8	32859911
AllCCS	[M+H-H2O]+	165.5	32859911
AllCCS	[M+NH4]+	171.9	32859911
AllCCS	[M+Na]+	172.8	32859911
AllCCS	[M-H]-	169.5	32859911
AllCCS	[M+Na-2H]-	169.2	32859911
AllCCS	[M+HCOO]-	169.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Riparin III	COC1=CC=C(CCNC(=O)C2=C(O)C=CC=C2O)C=C1	3574.0	Standard polar	33892256
Riparin III	COC1=CC=C(CCNC(=O)C2=C(O)C=CC=C2O)C=C1	2798.4	Standard non polar	33892256
Riparin III	COC1=CC=C(CCNC(=O)C2=C(O)C=CC=C2O)C=C1	2626.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Riparin III,3TMS,isomer #1	COC1=CC=C(CCN(C(=O)C2=C(O[Si](C)(C)C)C=CC=C2O[Si](C)(C)C)[Si](C)(C)C)C=C1	2766.8	Semi standard non polar	33892256
Riparin III,3TMS,isomer #1	COC1=CC=C(CCN(C(=O)C2=C(O[Si](C)(C)C)C=CC=C2O[Si](C)(C)C)[Si](C)(C)C)C=C1	2601.4	Standard non polar	33892256
Riparin III,3TMS,isomer #1	COC1=CC=C(CCN(C(=O)C2=C(O[Si](C)(C)C)C=CC=C2O[Si](C)(C)C)[Si](C)(C)C)C=C1	2922.4	Standard polar	33892256
Riparin III,3TBDMS,isomer #1	COC1=CC=C(CCN(C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC=C2O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3433.6	Semi standard non polar	33892256
Riparin III,3TBDMS,isomer #1	COC1=CC=C(CCN(C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC=C2O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3210.6	Standard non polar	33892256
Riparin III,3TBDMS,isomer #1	COC1=CC=C(CCN(C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC=C2O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3211.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Riparin III GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0910000000-08901ba0c3ca6422bd47	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riparin III GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riparin III GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riparin III GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riparin III GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riparin III GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riparin III GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riparin III GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riparin III GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riparin III GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	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

158755

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 Riparin III (HMDB0257239)

MOL for HMDB0257239 (Riparin III)

3D MOL for HMDB0257239 (Riparin III)

3D SDF for HMDB0257239 (Riparin III)

3D-SDF for HMDB0257239 (Riparin III)

PDB for HMDB0257239 (Riparin III)

3D PDB for HMDB0257239 (Riparin III)

SMILES for HMDB0257239 (Riparin III)

INCHI for HMDB0257239 (Riparin III)

Structure for HMDB0257239 (Riparin III)

3D Structure for HMDB0257239 (Riparin III)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra