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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:52:52 UTC

Update Date

2021-09-14 15:45:19 UTC

HMDB ID

HMDB0042008

Secondary Accession Numbers

HMDB42008

Metabolite Identification

Common Name

Ritalinic acid

Description

Ritalinic acid, also known as ritalinate, belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. Ritalinic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Ritalinic acid.

Structure

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

HMDB0042008
     RDKit          3D
Ritalinic acid
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.0195   -1.7541   -2.7914 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2479   -1.6705   -1.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5988   -2.8092   -0.8934 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1949   -0.3795   -0.8657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5400   -0.0659   -0.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2290    1.0770   -0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4732    1.3585   -0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0860    0.5381    0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4068   -0.5951    1.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1489   -0.8881    0.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8371   -0.5185    0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9682    0.7329    1.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1059    1.6124    0.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3781    0.8218    0.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9772   -0.1106   -0.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0629   -1.0788   -0.2192 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0214   -3.2373   -0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1276    0.4554   -1.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7480    1.7331   -1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9842    2.2422   -0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0729    0.7716    1.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8260   -1.2842    1.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6170   -1.7818    0.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3969   -1.2938    0.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0154    0.5363    2.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0201    1.3302    0.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3712    2.2453    1.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9328    2.2880   -0.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6171    0.2232    1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1551    1.5304    0.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8370   -0.6571   -1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4274    0.5028   -1.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9026   -1.8751   -0.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 10  5  1  0
 16 11  1  0
  3 17  1  0
  4 18  1  0
  6 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
M  END


  Mrv0541 09131211522D          

 16 17  0  0  0  0            999 V2000
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15 13  2  0  0  0  0
 16 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0042008

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C(C1CCCCN1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H17NO2/c15-13(16)12(10-6-2-1-3-7-10)11-8-4-5-9-14-11/h1-3,6-7,11-12,14H,4-5,8-9H2,(H,15,16)

> <INCHI_KEY>
INGSNVSERUZOAK-UHFFFAOYSA-N

> <FORMULA>
C13H17NO2

> <MOLECULAR_WEIGHT>
219.2796

> <EXACT_MASS>
219.125928793

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.863010734238017

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-phenyl-2-(piperidin-2-yl)acetic acid

> <ALOGPS_LOGP>
-0.32

> <JCHEM_LOGP>
-0.36274522975435597

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7341330440489644

> <JCHEM_PKA_STRONGEST_BASIC>
10.083137105462983

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
61.95910000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenyl(piperidin-2-yl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0042008
     RDKit          3D
Ritalinic acid
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.0195   -1.7541   -2.7914 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2479   -1.6705   -1.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5988   -2.8092   -0.8934 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1949   -0.3795   -0.8657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5400   -0.0659   -0.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2290    1.0770   -0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4732    1.3585   -0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0860    0.5381    0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4068   -0.5951    1.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1489   -0.8881    0.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8371   -0.5185    0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9682    0.7329    1.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1059    1.6124    0.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3781    0.8218    0.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9772   -0.1106   -0.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0629   -1.0788   -0.2192 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0214   -3.2373   -0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1276    0.4554   -1.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7480    1.7331   -1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9842    2.2422   -0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0729    0.7716    1.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8260   -1.2842    1.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6170   -1.7818    0.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3969   -1.2938    0.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0154    0.5363    2.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0201    1.3302    0.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3712    2.2453    1.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9328    2.2880   -0.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6171    0.2232    1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1551    1.5304    0.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8370   -0.6571   -1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4274    0.5028   -1.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9026   -1.8751   -0.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 10  5  1  0
 16 11  1  0
  3 17  1  0
  4 18  1  0
  6 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       1.334   8.470   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       5.335  10.780   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    5    8                                                       
CONECT    5    4    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   10                                                       
CONECT    8    4   11                                                       
CONECT    9    5   14                                                       
CONECT   10    6    7   12                                                  
CONECT   11    8   12   14                                                  
CONECT   12   10   11   13                                                  
CONECT   13   12   15   16                                                  
CONECT   14    9   11                                                       
CONECT   15   13                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0042008
HETATM    1  O1  UNL     1      -0.019  -1.754  -2.791  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.248  -1.670  -1.578  1.00  0.00           C  
HETATM    3  O2  UNL     1       0.599  -2.809  -0.893  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.195  -0.380  -0.866  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.540  -0.066  -0.309  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.229   1.077  -0.704  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.473   1.358  -0.180  1.00  0.00           C  
HETATM    8  C6  UNL     1       4.086   0.538   0.743  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.407  -0.595   1.137  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.149  -0.888   0.613  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.837  -0.519   0.260  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.968   0.733   1.042  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.106   1.612   0.685  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.378   0.822   0.364  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.977  -0.111  -0.774  1.00  0.00           C  
HETATM   16  N1  UNL     1      -2.063  -1.079  -0.219  1.00  0.00           N  
HETATM   17  H1  UNL     1      -0.021  -3.237  -0.195  1.00  0.00           H  
HETATM   18  H2  UNL     1      -0.128   0.455  -1.550  1.00  0.00           H  
HETATM   19  H3  UNL     1       1.748   1.733  -1.437  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.984   2.242  -0.498  1.00  0.00           H  
HETATM   21  H5  UNL     1       5.073   0.772   1.152  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.826  -1.284   1.858  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.617  -1.782   0.928  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.397  -1.294   0.953  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.015   0.536   2.152  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.020   1.330   0.894  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.371   2.245   1.580  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.933   2.288  -0.165  1.00  0.00           H  
HETATM   29  H13 UNL     1      -3.617   0.223   1.268  1.00  0.00           H  
HETATM   30  H14 UNL     1      -4.155   1.530   0.084  1.00  0.00           H  
HETATM   31  H15 UNL     1      -3.837  -0.657  -1.186  1.00  0.00           H  
HETATM   32  H16 UNL     1      -2.427   0.503  -1.498  1.00  0.00           H  
HETATM   33  H17 UNL     1      -1.903  -1.875  -0.869  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   17
CONECT    4    5   11   18
CONECT    5    6    6   10
CONECT    6    7   19
CONECT    7    8    8   20
CONECT    8    9   21
CONECT    9   10   10   22
CONECT   10   23
CONECT   11   12   16   24
CONECT   12   13   25   26
CONECT   13   14   27   28
CONECT   14   15   29   30
CONECT   15   16   31   32
CONECT   16   33
END

HMDB0042008
     RDKit          3D
Ritalinic acid
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.0195   -1.7541   -2.7914 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2479   -1.6705   -1.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5988   -2.8092   -0.8934 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1949   -0.3795   -0.8657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5400   -0.0659   -0.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2290    1.0770   -0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4732    1.3585   -0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0860    0.5381    0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4068   -0.5951    1.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1489   -0.8881    0.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8371   -0.5185    0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9682    0.7329    1.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1059    1.6124    0.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3781    0.8218    0.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9772   -0.1106   -0.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0629   -1.0788   -0.2192 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0214   -3.2373   -0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1276    0.4554   -1.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7480    1.7331   -1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9842    2.2422   -0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0729    0.7716    1.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8260   -1.2842    1.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6170   -1.7818    0.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3969   -1.2938    0.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0154    0.5363    2.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0201    1.3302    0.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3712    2.2453    1.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9328    2.2880   -0.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6171    0.2232    1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1551    1.5304    0.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8370   -0.6571   -1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4274    0.5028   -1.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9026   -1.8751   -0.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 10  5  1  0
 16 11  1  0
  3 17  1  0
  4 18  1  0
  6 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
alpha-Phenyl-2-piperidineacetic acid	ChEBI
a-Phenyl-2-piperidineacetate	Generator
a-Phenyl-2-piperidineacetic acid	Generator
alpha-Phenyl-2-piperidineacetate	Generator
Α-phenyl-2-piperidineacetate	Generator
Α-phenyl-2-piperidineacetic acid	Generator
Ritalinate	Generator
Ritalinic acid, (r,r)-(+-)-isomer	HMDB

Chemical Formula

C₁₃H₁₇NO₂

Average Molecular Weight

219.2796

Monoisotopic Molecular Weight

219.125928793

IUPAC Name

2-phenyl-2-(piperidin-2-yl)acetic acid

Traditional Name

phenyl(piperidin-2-yl)acetic acid

CAS Registry Number

19395-41-6

SMILES

OC(=O)C(C1CCCCN1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C13H17NO2/c15-13(16)12(10-6-2-1-3-7-10)11-8-4-5-9-14-11/h1-3,6-7,11-12,14H,4-5,8-9H2,(H,15,16)

InChI Key

INGSNVSERUZOAK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Aralkylamines

Alternative Parents

Substituents

Aralkylamine
Monocyclic benzene moiety
Piperidine
Benzenoid
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Secondary amine
Organoheterocyclic compound
Azacycle
Carbonyl group
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:83481 )
monocarboxylic acid (CHEBI:83481 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0042008)

Organ

Liver (HMDB: HMDB0042008)
Kidney (HMDB: HMDB0042008)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0042008)

Cellular substructure

Cytoplasm (HMDB: HMDB0042008)

Source

Endogenous

Endogenous (HMDB: HMDB0042008)

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	150.0	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.62 g/L	ALOGPS
logP	-0.32	ALOGPS
logP	-0.36	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.73	ChemAxon
pKa (Strongest Basic)	10.08	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	61.96 m³·mol⁻¹	ChemAxon
Polarizability	23.86 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	151.526	31661259
DarkChem	[M-H]-	145.573	31661259
DeepCCS	[M+H]+	149.426	30932474
DeepCCS	[M-H]-	147.03	30932474
DeepCCS	[M-2H]-	181.115	30932474
DeepCCS	[M+Na]+	155.728	30932474
AllCCS	[M+H]+	151.2	32859911
AllCCS	[M+H-H2O]+	147.0	32859911
AllCCS	[M+NH4]+	155.1	32859911
AllCCS	[M+Na]+	156.2	32859911
AllCCS	[M-H]-	155.2	32859911
AllCCS	[M+Na-2H]-	155.5	32859911
AllCCS	[M+HCOO]-	155.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.91 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7647 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.82 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	196.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	891.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	240.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	124.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	169.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	86.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	290.6 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	308.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	531.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	726.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	290.9 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	814.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	196.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	243.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	595.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	353.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	113.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ritalinic acid	OC(=O)C(C1CCCCN1)C1=CC=CC=C1	2534.8	Standard polar	33892256
Ritalinic acid	OC(=O)C(C1CCCCN1)C1=CC=CC=C1	1924.7	Standard non polar	33892256
Ritalinic acid	OC(=O)C(C1CCCCN1)C1=CC=CC=C1	1875.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ritalinic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(C1=CC=CC=C1)C1CCCCN1	1834.9	Semi standard non polar	33892256
Ritalinic acid,1TMS,isomer #2	C[Si](C)(C)N1CCCCC1C(C(=O)O)C1=CC=CC=C1	1938.6	Semi standard non polar	33892256
Ritalinic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(C1=CC=CC=C1)C1CCCCN1[Si](C)(C)C	1928.3	Semi standard non polar	33892256
Ritalinic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(C1=CC=CC=C1)C1CCCCN1[Si](C)(C)C	1957.1	Standard non polar	33892256
Ritalinic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(C1=CC=CC=C1)C1CCCCN1	2062.6	Semi standard non polar	33892256
Ritalinic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCCCC1C(C(=O)O)C1=CC=CC=C1	2170.9	Semi standard non polar	33892256
Ritalinic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(C1=CC=CC=C1)C1CCCCN1[Si](C)(C)C(C)(C)C	2380.3	Semi standard non polar	33892256
Ritalinic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(C1=CC=CC=C1)C1CCCCN1[Si](C)(C)C(C)(C)C	2349.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ritalinic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9300000000-dc71fffe4d675962db98	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ritalinic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00e9-9520000000-ab57a14766f106dcb1b7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ritalinic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ritalinic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ritalinic acid LC-ESI-ITFT , negative-QTOF	splash10-00di-0900000000-5349879fc5f8fc76b391	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ritalinic acid LC-ESI-ITFT , negative-QTOF	splash10-00di-0900000000-95b28a43f0777e9401ba	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ritalinic acid LC-ESI-ITFT , negative-QTOF	splash10-00di-0900000000-2cd3ebd39ba590055567	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ritalinic acid LC-ESI-ITFT , negative-QTOF	splash10-00di-0900000000-5349879fc5f8fc76b391	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ritalinic acid LC-ESI-ITFT , negative-QTOF	splash10-00di-0900000000-075b4840fbe857e8ccd5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ritalinic acid LC-ESI-ITFT , positive-QTOF	splash10-001i-9000000000-210f28bbecb4977a5c73	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ritalinic acid LC-ESI-ITFT , positive-QTOF	splash10-00di-0090000000-000b03fadb8e0e2d157f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ritalinic acid LC-ESI-ITFT , positive-QTOF	splash10-00di-2090000000-bd71fa6fb9aa28c3acbc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ritalinic acid LC-ESI-ITFT , positive-QTOF	splash10-001i-9030000000-c0a3a1f5012bbceaa097	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ritalinic acid LC-ESI-ITFT , positive-QTOF	splash10-001i-9000000000-95395a90021329c45c72	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ritalinic acid LC-ESI-ITFT , positive-QTOF	splash10-001i-9000000000-6fe94992bc8c559c4637	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ritalinic acid LC-ESI-ITFT , positive-QTOF	splash10-001i-9000000000-73161376dc9cb328306e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ritalinic acid LC-ESI-ITFT , positive-QTOF	splash10-00di-0090000000-e7f25e818947f99330e8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ritalinic acid LC-ESI-ITFT , positive-QTOF	splash10-00di-2090000000-2ca8b1684e34e53b75e1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ritalinic acid LC-ESI-ITFT , positive-QTOF	splash10-001i-9020000000-2c2191b99d6ac20c55fb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ritalinic acid LC-ESI-ITFT , positive-QTOF	splash10-001i-9000000000-d71faf730653bf91a556	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ritalinic acid LC-ESI-ITFT , positive-QTOF	splash10-001i-9000000000-77b8b619d738c3b695a6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ritalinic acid LC-ESI-ITFT , positive-QTOF	splash10-001i-9000000000-de04d59769d400990721	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ritalinic acid LC-ESI-ITFT , positive-QTOF	splash10-001i-9000000000-aa4185502c8a9a60efae	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ritalinic acid 10V, Positive-QTOF	splash10-00di-1390000000-048fb36cd4edbad95c33	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ritalinic acid 20V, Positive-QTOF	splash10-0fl0-6960000000-9328f8392654359c6eb9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ritalinic acid 40V, Positive-QTOF	splash10-003r-9400000000-8ae7fa901297e62a7518	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ritalinic acid 10V, Negative-QTOF	splash10-00xr-0970000000-1096f4480c2201e7f4a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ritalinic acid 20V, Negative-QTOF	splash10-00di-2910000000-662a13b5c79c77499c05	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ritalinic acid 40V, Negative-QTOF	splash10-003r-9500000000-c47bd04961e3ff01ba1c	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78360

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ritalinic acid

METLIN ID

Not Available

PubChem Compound

86863

PDB ID

Not Available

ChEBI ID

83481

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

Paterson SM, Moore GA, Florkowski CM, George PM: Determination of methylphenidate and its metabolite ritalinic acid in urine by liquid chromatography/tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Jan 15;881-882:20-6. doi: 10.1016/j.jchromb.2011.11.007. Epub 2011 Nov 28. [PubMed:22204874 ]
Beck O, Stephanson N, Sandqvist S, Franck J: Determination of amphetamine and methylphenidate in exhaled breath of patients undergoing attention-deficit/hyperactivity disorder treatment. Ther Drug Monit. 2014 Aug;36(4):528-34. doi: 10.1097/FTD.0000000000000046. [PubMed:24452069 ]
Gahr M, Kolle MA: Methylphenidate intoxication: somnolence as an uncommon clinical symptom and proof of overdosing by increased serum levels of ritalinic acid. Pharmacopsychiatry. 2014 Sep;47(6):215-8. doi: 10.1055/s-0034-1387700. Epub 2014 Aug 14. [PubMed:25121992 ]

Showing metabocard for Ritalinic acid (HMDB0042008)

MOL for HMDB0042008 (Ritalinic acid)

3D MOL for HMDB0042008 (Ritalinic acid)

3D SDF for HMDB0042008 (Ritalinic acid)

3D-SDF for HMDB0042008 (Ritalinic acid)

PDB for HMDB0042008 (Ritalinic acid)

3D PDB for HMDB0042008 (Ritalinic acid)

SMILES for HMDB0042008 (Ritalinic acid)

INCHI for HMDB0042008 (Ritalinic acid)

Structure for HMDB0042008 (Ritalinic acid)

3D Structure for HMDB0042008 (Ritalinic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra