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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:39:21 UTC

Update Date

2021-09-26 23:03:16 UTC

HMDB ID

HMDB0251319

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dihydrokainic acid

Description

52497-36-6, also known as dihydrokainate, belongs to the class of organic compounds known as kainoids. These are non-proteigenous amino acids with a structure characterized by the presence of a pyrrolidine ring bearing two dicarboxylic acid groups. Based on a literature review very few articles have been published on 52497-36-6. This compound has been identified in human blood as reported by (PMID: 31557052 ). Dihydrokainic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dihydrokainic acid 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

HMDB0251319
     RDKit          3D
Dihydrokainic acid
 32 32  0  0  0  0  0  0  0  0999 V2000
    2.9939   -0.9882    0.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8476   -0.0732   -0.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3824    1.3201   -0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7253   -0.3392    0.7239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3679   -1.8233    0.6984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9610   -1.7951    1.2987 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6120   -0.6540    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0972   -1.1156   -0.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8877   -2.3371   -0.9954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7698   -0.3151   -1.5790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5237    0.4049    0.5812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7003    1.3476   -0.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0283    2.0184   -0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4780    2.7655   -1.3788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8177    1.8098    0.6321 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9943   -0.8559    1.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9179   -0.5600   -0.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8278   -2.0271   -0.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6835   -0.3425   -1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3904    1.8451   -1.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    1.8894    0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4761    1.2902    0.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1776   -0.1936    1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636   -2.4029    1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2965   -2.2273   -0.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8828   -1.6191    2.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4398   -0.3706    1.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7530   -0.1138   -1.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6789    1.0147    1.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0844    2.0894   -0.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7075    0.7454   -1.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7969    1.6132    0.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 11  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 15 32  1  0
M  END


  Mrv1652309112110392D          

 15 15  0  0  0  0            999 V2000
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3259   -0.4747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2820    0.5872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  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
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251319

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1CNC(C1CC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H17NO4/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13/h5-7,9,11H,3-4H2,1-2H3,(H,12,13)(H,14,15)

> <INCHI_KEY>
JQPDCKOQOOQUSC-UHFFFAOYSA-N

> <FORMULA>
C10H17NO4

> <MOLECULAR_WEIGHT>
215.249

> <EXACT_MASS>
215.115758031

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
21.874745999454923

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(carboxymethyl)-4-(propan-2-yl)pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-1.31

> <JCHEM_LOGP>
-2.0161020847181352

> <ALOGPS_LOGS>
-1.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.53610193905541

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.792786583608264

> <JCHEM_PKA_STRONGEST_BASIC>
11.701135210374424

> <JCHEM_POLAR_SURFACE_AREA>
86.63000000000001

> <JCHEM_REFRACTIVITY>
52.42350000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(carboxymethyl)-4-isopropylpyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251319
     RDKit          3D
Dihydrokainic acid
 32 32  0  0  0  0  0  0  0  0999 V2000
    2.9939   -0.9882    0.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8476   -0.0732   -0.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3824    1.3201   -0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7253   -0.3392    0.7239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3679   -1.8233    0.6984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9610   -1.7951    1.2987 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6120   -0.6540    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0972   -1.1156   -0.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8877   -2.3371   -0.9954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7698   -0.3151   -1.5790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5237    0.4049    0.5812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7003    1.3476   -0.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0283    2.0184   -0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4780    2.7655   -1.3788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8177    1.8098    0.6321 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9943   -0.8559    1.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9179   -0.5600   -0.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8278   -2.0271   -0.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6835   -0.3425   -1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3904    1.8451   -1.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    1.8894    0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4761    1.2902    0.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1776   -0.1936    1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636   -2.4029    1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2965   -2.2273   -0.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8828   -1.6191    2.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4398   -0.3706    1.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7530   -0.1138   -1.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6789    1.0147    1.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0844    2.0894   -0.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7075    0.7454   -1.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7969    1.6132    0.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 11  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 15 32  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.795   0.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.475  -0.886   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.260   1.096   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.011  -2.943   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -2.147  -1.375   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    4    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0251319
HETATM    1  C1  UNL     1       2.994  -0.988   0.274  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.848  -0.073  -0.230  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.382   1.320  -0.026  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.725  -0.339   0.724  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.368  -1.823   0.698  1.00  0.00           C  
HETATM    6  N1  UNL     1      -0.961  -1.795   1.299  1.00  0.00           N  
HETATM    7  C6  UNL     1      -1.612  -0.654   0.642  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.097  -1.116  -0.669  1.00  0.00           C  
HETATM    9  O1  UNL     1      -1.888  -2.337  -0.995  1.00  0.00           O  
HETATM   10  O2  UNL     1      -2.770  -0.315  -1.579  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.524   0.405   0.581  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.700   1.348  -0.545  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.028   2.018  -0.481  1.00  0.00           C  
HETATM   14  O3  UNL     1      -2.478   2.766  -1.379  1.00  0.00           O  
HETATM   15  O4  UNL     1      -2.818   1.810   0.632  1.00  0.00           O  
HETATM   16  H1  UNL     1       2.994  -0.856   1.383  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.918  -0.560  -0.153  1.00  0.00           H  
HETATM   18  H3  UNL     1       2.828  -2.027  -0.036  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.684  -0.343  -1.265  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.390   1.845  -1.016  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.905   1.889   0.767  1.00  0.00           H  
HETATM   22  H7  UNL     1       3.476   1.290   0.265  1.00  0.00           H  
HETATM   23  H8  UNL     1       1.178  -0.194   1.753  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.064  -2.403   1.350  1.00  0.00           H  
HETATM   25  H10 UNL     1       0.296  -2.227  -0.309  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.883  -1.619   2.323  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.440  -0.371   1.322  1.00  0.00           H  
HETATM   28  H13 UNL     1      -3.753  -0.114  -1.538  1.00  0.00           H  
HETATM   29  H14 UNL     1      -0.679   1.015   1.527  1.00  0.00           H  
HETATM   30  H15 UNL     1       0.084   2.089  -0.696  1.00  0.00           H  
HETATM   31  H16 UNL     1      -0.708   0.745  -1.503  1.00  0.00           H  
HETATM   32  H17 UNL     1      -3.797   1.613   0.486  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    4   19
CONECT    3   20   21   22
CONECT    4    5   11   23
CONECT    5    6   24   25
CONECT    6    7   26
CONECT    7    8   11   27
CONECT    8    9    9   10
CONECT   10   28
CONECT   11   12   29
CONECT   12   13   30   31
CONECT   13   14   14   15
CONECT   15   32
END

HMDB0251319
     RDKit          3D
Dihydrokainic acid
 32 32  0  0  0  0  0  0  0  0999 V2000
    2.9939   -0.9882    0.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8476   -0.0732   -0.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3824    1.3201   -0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7253   -0.3392    0.7239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3679   -1.8233    0.6984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9610   -1.7951    1.2987 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6120   -0.6540    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0972   -1.1156   -0.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8877   -2.3371   -0.9954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7698   -0.3151   -1.5790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5237    0.4049    0.5812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7003    1.3476   -0.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0283    2.0184   -0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4780    2.7655   -1.3788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8177    1.8098    0.6321 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9943   -0.8559    1.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9179   -0.5600   -0.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8278   -2.0271   -0.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6835   -0.3425   -1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3904    1.8451   -1.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    1.8894    0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4761    1.2902    0.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1776   -0.1936    1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636   -2.4029    1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2965   -2.2273   -0.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8828   -1.6191    2.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4398   -0.3706    1.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7530   -0.1138   -1.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6789    1.0147    1.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0844    2.0894   -0.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7075    0.7454   -1.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7969    1.6132    0.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 11  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 15 32  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Dihydrokainate	MeSH
Dihydrokainic acid	MeSH

Chemical Formula

C₁₀H₁₇NO₄

Average Molecular Weight

215.249

Monoisotopic Molecular Weight

215.115758031

IUPAC Name

3-(carboxymethyl)-4-(propan-2-yl)pyrrolidine-2-carboxylic acid

Traditional Name

3-(carboxymethyl)-4-isopropylpyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(C)C1CNC(C1CC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C10H17NO4/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13/h5-7,9,11H,3-4H2,1-2H3,(H,12,13)(H,14,15)

InChI Key

JQPDCKOQOOQUSC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kainoids. These are non-proteigenous amino acids with a structure characterized by the presence of a pyrrolidine ring bearing two dicarboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Kainoids

Alternative Parents

Substituents

Kainoid skeleton
Proline or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Dicarboxylic acid or derivatives
Pyrrolidine
Amino acid
Secondary amine
Azacycle
Secondary aliphatic amine
Carboxylic acid
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Amine
Organic oxygen compound
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	-1.3	ALOGPS
logP	-2	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.79	ChemAxon
pKa (Strongest Basic)	11.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	52.42 m³·mol⁻¹	ChemAxon
Polarizability	21.87 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	146.036	30932474
DeepCCS	[M-H]-	142.209	30932474
DeepCCS	[M-2H]-	179.636	30932474
DeepCCS	[M+Na]+	155.3	30932474
AllCCS	[M+H]+	147.6	32859911
AllCCS	[M+H-H2O]+	143.9	32859911
AllCCS	[M+NH4]+	151.1	32859911
AllCCS	[M+Na]+	152.1	32859911
AllCCS	[M-H]-	148.3	32859911
AllCCS	[M+Na-2H]-	149.0	32859911
AllCCS	[M+HCOO]-	149.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydrokainic acid	CC(C)C1CNC(C1CC(O)=O)C(O)=O	3042.2	Standard polar	33892256
Dihydrokainic acid	CC(C)C1CNC(C1CC(O)=O)C(O)=O	1608.3	Standard non polar	33892256
Dihydrokainic acid	CC(C)C1CNC(C1CC(O)=O)C(O)=O	1922.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydrokainic acid,3TMS,isomer #1	CC(C)C1CN([Si](C)(C)C)C(C(=O)O[Si](C)(C)C)C1CC(=O)O[Si](C)(C)C	1913.8	Semi standard non polar	33892256
Dihydrokainic acid,3TMS,isomer #1	CC(C)C1CN([Si](C)(C)C)C(C(=O)O[Si](C)(C)C)C1CC(=O)O[Si](C)(C)C	1986.5	Standard non polar	33892256
Dihydrokainic acid,3TMS,isomer #1	CC(C)C1CN([Si](C)(C)C)C(C(=O)O[Si](C)(C)C)C1CC(=O)O[Si](C)(C)C	2075.2	Standard polar	33892256
Dihydrokainic acid,3TBDMS,isomer #1	CC(C)C1CN([Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)O[Si](C)(C)C(C)(C)C	2564.5	Semi standard non polar	33892256
Dihydrokainic acid,3TBDMS,isomer #1	CC(C)C1CN([Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)O[Si](C)(C)C(C)(C)C	2615.7	Standard non polar	33892256
Dihydrokainic acid,3TBDMS,isomer #1	CC(C)C1CN([Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)O[Si](C)(C)C(C)(C)C	2475.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrokainic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-7900000000-ef0cc56c1a0f4177a406	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrokainic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrokainic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrokainic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrokainic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrokainic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrokainic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrokainic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrokainic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrokainic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrokainic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrokainic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrokainic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrokainic acid GC-MS (TBDMS_2_3) - 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 - Dihydrokainic acid 10V, Positive-QTOF	splash10-014i-0490000000-14fd8bd860395d1823f1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrokainic acid 20V, Positive-QTOF	splash10-01b9-3930000000-3b86ce40e1b42dea33e6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrokainic acid 40V, Positive-QTOF	splash10-0002-9200000000-97d13aeeeae39a12de07	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrokainic acid 10V, Negative-QTOF	splash10-03di-0290000000-6ff590e77a031951fcc7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrokainic acid 20V, Negative-QTOF	splash10-11b9-4920000000-087e83058ccb30d958ef	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrokainic acid 40V, Negative-QTOF	splash10-0006-9710000000-829e52a7699c32ff896c	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	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

1588

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1650

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 Dihydrokainic acid (HMDB0251319)

MOL for HMDB0251319 (Dihydrokainic acid)

3D MOL for HMDB0251319 (Dihydrokainic acid)

3D SDF for HMDB0251319 (Dihydrokainic acid)

3D-SDF for HMDB0251319 (Dihydrokainic acid)

PDB for HMDB0251319 (Dihydrokainic acid)

3D PDB for HMDB0251319 (Dihydrokainic acid)

SMILES for HMDB0251319 (Dihydrokainic acid)

INCHI for HMDB0251319 (Dihydrokainic acid)

Structure for HMDB0251319 (Dihydrokainic acid)

3D Structure for HMDB0251319 (Dihydrokainic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra