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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:28:26 UTC

Update Date

2021-09-26 23:07:03 UTC

HMDB ID

HMDB0253672

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Isopilocarpinic acid

Description

Isopilocarpinic acid, also known as isopilocarpinate, belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring. Based on a literature review a significant number of articles have been published on Isopilocarpinic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Isopilocarpinic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Isopilocarpinic 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

HMDB0253672
     RDKit          3D
Isopilocarpinic acid
 34 34  0  0  0  0  0  0  0  0999 V2000
   -3.7497   -0.7072   -1.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5254    0.1692   -1.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5012   -0.4913   -0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0137   -0.8009    1.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0720   -1.9598    1.7097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4820    0.2179    2.0759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528    0.1463   -0.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1430    1.5738    0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9274    2.4050   -0.4446 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8564   -0.6861    0.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1862   -0.0710    0.6738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6545    0.8294    1.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9123    1.1281    1.2358 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1960    0.4362    0.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463   -0.3039   -0.2393 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1052   -1.1769   -1.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0666   -1.2266   -0.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5774   -0.0068   -1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5927   -1.4559   -2.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1192    0.3970   -2.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8490    1.1647   -0.5744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3435   -1.5165   -0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3976    0.1120    2.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2391    0.1816   -1.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8893    1.9821    0.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4196    1.6517    1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3046    3.1483    0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4647   -0.9153    1.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8814   -1.6838    0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1347    1.2367    2.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1705    0.5101   -0.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1737   -1.7410   -1.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2914   -0.6117   -2.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9358   -1.9356   -1.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 11  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 12 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
M  END

  Mrv1652309112114282D          

 16 16  0  0  0  0            999 V2000
    3.2755    0.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610    0.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610   -0.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8465   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8465   -2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1321   -2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0458   -3.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2389   -3.4406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1736   -2.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3784   -2.1130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2069   -1.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1321   -0.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1321    0.0264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2755   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9899   -0.7986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2755   -2.0361    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253672

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(C(CO)CC1=CN=CN1C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H18N2O3/c1-3-10(11(15)16)8(6-14)4-9-5-12-7-13(9)2/h5,7-8,10,14H,3-4,6H2,1-2H3,(H,15,16)

> <INCHI_KEY>
WJRPDGADPABWOY-UHFFFAOYSA-N

> <FORMULA>
C11H18N2O3

> <MOLECULAR_WEIGHT>
226.276

> <EXACT_MASS>
226.131742448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
23.929561806425035

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-ethyl-4-hydroxy-3-[(1-methyl-1H-imidazol-5-yl)methyl]butanoic acid

> <ALOGPS_LOGP>
-0.21

> <JCHEM_LOGP>
-0.48248629315802605

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.456821461163297

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.339910898057834

> <JCHEM_PKA_STRONGEST_BASIC>
6.611280399920509

> <JCHEM_POLAR_SURFACE_AREA>
75.35

> <JCHEM_REFRACTIVITY>
60.0264

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-ethyl-4-hydroxy-3-[(3-methylimidazol-4-yl)methyl]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253672
     RDKit          3D
Isopilocarpinic acid
 34 34  0  0  0  0  0  0  0  0999 V2000
   -3.7497   -0.7072   -1.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5254    0.1692   -1.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5012   -0.4913   -0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0137   -0.8009    1.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0720   -1.9598    1.7097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4820    0.2179    2.0759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528    0.1463   -0.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1430    1.5738    0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9274    2.4050   -0.4446 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8564   -0.6861    0.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1862   -0.0710    0.6738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6545    0.8294    1.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9123    1.1281    1.2358 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1960    0.4362    0.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463   -0.3039   -0.2393 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1052   -1.1769   -1.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0666   -1.2266   -0.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5774   -0.0068   -1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5927   -1.4559   -2.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1192    0.3970   -2.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8490    1.1647   -0.5744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3435   -1.5165   -0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3976    0.1120    2.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2391    0.1816   -1.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8893    1.9821    0.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4196    1.6517    1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3046    3.1483    0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4647   -0.9153    1.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8814   -1.6838    0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1347    1.2367    2.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1705    0.5101   -0.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1737   -1.7410   -1.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2914   -0.6117   -2.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9358   -1.9356   -1.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 11  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 12 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  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       6.114   0.819   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.781   0.049   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.781  -1.491   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.447  -2.261   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.447  -3.801   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.113  -4.571   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.952  -6.102   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.446  -6.422   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.324  -5.089   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.706  -3.944   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       0.386  -2.438   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.113  -1.491   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.113   0.049   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.114  -2.261   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.448  -1.491   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.114  -3.801   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10                                                            
CONECT   12    4   13                                                       
CONECT   13   12                                                            
CONECT   14    3   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0256548
HETATM    1  C1  UNL     1       3.277  -2.025  -0.140  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.822  -1.660   0.202  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.783  -0.159   0.562  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.248   0.549  -0.640  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.123  -0.004  -1.801  1.00  0.00           O  
HETATM    6  O2  UNL     1       2.833   1.802  -0.676  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.419   0.206   1.087  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.416   1.672   1.438  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.663   2.445   0.320  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.581  -0.149   0.047  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.987   0.093   0.361  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.655   0.463   1.495  1.00  0.00           C  
HETATM   13  N1  UNL     1      -3.986   0.577   1.239  1.00  0.00           N  
HETATM   14  C10 UNL     1      -4.134   0.276  -0.056  1.00  0.00           C  
HETATM   15  N2  UNL     1      -2.961  -0.015  -0.598  1.00  0.00           N  
HETATM   16  C11 UNL     1      -2.759  -0.390  -2.002  1.00  0.00           C  
HETATM   17  H1  UNL     1       3.521  -3.048   0.208  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.446  -2.009  -1.234  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.972  -1.295   0.340  1.00  0.00           H  
HETATM   20  H4  UNL     1       1.254  -1.852  -0.730  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.414  -2.268   0.998  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.481  -0.063   1.419  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.696   2.365  -1.499  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.277  -0.399   2.013  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.315   1.786   2.131  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.485   2.057   1.901  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.222   2.636  -0.125  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.504  -1.275  -0.080  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.250   0.270  -0.920  1.00  0.00           H  
HETATM   30  H14 UNL     1      -2.169   0.620   2.456  1.00  0.00           H  
HETATM   31  H15 UNL     1      -5.078   0.266  -0.609  1.00  0.00           H  
HETATM   32  H16 UNL     1      -3.265  -1.358  -2.190  1.00  0.00           H  
HETATM   33  H17 UNL     1      -1.701  -0.507  -2.255  1.00  0.00           H  
HETATM   34  H18 UNL     1      -3.225   0.392  -2.661  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4    7   22
CONECT    4    5    5    6
CONECT    6   23
CONECT    7    8   10   24
CONECT    8    9   25   26
CONECT    9   27
CONECT   10   11   28   29
CONECT   11   12   12   15
CONECT   12   13   30
CONECT   13   14   14
CONECT   14   15   31
CONECT   15   16
CONECT   16   32   33   34
END

HMDB0253672
     RDKit          3D
Isopilocarpinic acid
 34 34  0  0  0  0  0  0  0  0999 V2000
   -3.7497   -0.7072   -1.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5254    0.1692   -1.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5012   -0.4913   -0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0137   -0.8009    1.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0720   -1.9598    1.7097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4820    0.2179    2.0759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528    0.1463   -0.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1430    1.5738    0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9274    2.4050   -0.4446 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8564   -0.6861    0.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1862   -0.0710    0.6738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6545    0.8294    1.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9123    1.1281    1.2358 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1960    0.4362    0.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463   -0.3039   -0.2393 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1052   -1.1769   -1.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0666   -1.2266   -0.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5774   -0.0068   -1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5927   -1.4559   -2.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1192    0.3970   -2.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8490    1.1647   -0.5744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3435   -1.5165   -0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3976    0.1120    2.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2391    0.1816   -1.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8893    1.9821    0.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4196    1.6517    1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3046    3.1483    0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4647   -0.9153    1.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8814   -1.6838    0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1347    1.2367    2.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1705    0.5101   -0.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1737   -1.7410   -1.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2914   -0.6117   -2.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9358   -1.9356   -1.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 11  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 12 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Isopilocarpinate	Generator
2-Ethyl-4-hydroxy-3-[(1-methyl-1H-imidazol-5-yl)methyl]butanoate	HMDB

Chemical Formula

C₁₁H₁₈N₂O₃

Average Molecular Weight

226.276

Monoisotopic Molecular Weight

226.131742448

IUPAC Name

2-ethyl-4-hydroxy-3-[(1-methyl-1H-imidazol-5-yl)methyl]butanoic acid

Traditional Name

2-ethyl-4-hydroxy-3-[(3-methylimidazol-4-yl)methyl]butanoic acid

CAS Registry Number

Not Available

SMILES

CCC(C(CO)CC1=CN=CN1C)C(O)=O

InChI Identifier

InChI=1S/C11H18N2O3/c1-3-10(11(15)16)8(6-14)4-9-5-12-7-13(9)2/h5,7-8,10,14H,3-4,6H2,1-2H3,(H,15,16)

InChI Key

WJRPDGADPABWOY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

Imidazolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Imidazolyl carboxylic acid derivative
N-substituted imidazole
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Alcohol
Primary alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	-0.21	ALOGPS
logP	-0.48	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	4.34	ChemAxon
pKa (Strongest Basic)	6.61	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.35 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	60.03 m³·mol⁻¹	ChemAxon
Polarizability	23.93 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]+	150.186	30932474
DeepCCS	[M-H]-	146.358	30932474
DeepCCS	[M-2H]-	183.526	30932474
DeepCCS	[M+Na]+	159.19	30932474
AllCCS	[M+H]+	151.9	32859911
AllCCS	[M+H-H2O]+	148.2	32859911
AllCCS	[M+NH4]+	155.3	32859911
AllCCS	[M+Na]+	156.3	32859911
AllCCS	[M-H]-	152.4	32859911
AllCCS	[M+Na-2H]-	153.0	32859911
AllCCS	[M+HCOO]-	153.7	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isopilocarpinic acid,1TMS,isomer #1	CCC(C(=O)O)C(CO[Si](C)(C)C)CC1=CN=CN1C	2110.6	Semi standard non polar	33892256
Isopilocarpinic acid,1TMS,isomer #1	CCC(C(=O)O)C(CO[Si](C)(C)C)CC1=CN=CN1C	1946.3	Standard non polar	33892256
Isopilocarpinic acid,1TMS,isomer #1	CCC(C(=O)O)C(CO[Si](C)(C)C)CC1=CN=CN1C	2681.5	Standard polar	33892256
Isopilocarpinic acid,1TMS,isomer #2	CCC(C(=O)O[Si](C)(C)C)C(CO)CC1=CN=CN1C	2050.4	Semi standard non polar	33892256
Isopilocarpinic acid,1TMS,isomer #2	CCC(C(=O)O[Si](C)(C)C)C(CO)CC1=CN=CN1C	1896.5	Standard non polar	33892256
Isopilocarpinic acid,1TMS,isomer #2	CCC(C(=O)O[Si](C)(C)C)C(CO)CC1=CN=CN1C	2628.7	Standard polar	33892256
Isopilocarpinic acid,2TMS,isomer #1	CCC(C(=O)O[Si](C)(C)C)C(CO[Si](C)(C)C)CC1=CN=CN1C	2069.9	Semi standard non polar	33892256
Isopilocarpinic acid,2TMS,isomer #1	CCC(C(=O)O[Si](C)(C)C)C(CO[Si](C)(C)C)CC1=CN=CN1C	1979.7	Standard non polar	33892256
Isopilocarpinic acid,2TMS,isomer #1	CCC(C(=O)O[Si](C)(C)C)C(CO[Si](C)(C)C)CC1=CN=CN1C	2322.8	Standard polar	33892256
Isopilocarpinic acid,1TBDMS,isomer #1	CCC(C(=O)O)C(CO[Si](C)(C)C(C)(C)C)CC1=CN=CN1C	2341.0	Semi standard non polar	33892256
Isopilocarpinic acid,1TBDMS,isomer #1	CCC(C(=O)O)C(CO[Si](C)(C)C(C)(C)C)CC1=CN=CN1C	2175.4	Standard non polar	33892256
Isopilocarpinic acid,1TBDMS,isomer #1	CCC(C(=O)O)C(CO[Si](C)(C)C(C)(C)C)CC1=CN=CN1C	2778.9	Standard polar	33892256
Isopilocarpinic acid,1TBDMS,isomer #2	CCC(C(=O)O[Si](C)(C)C(C)(C)C)C(CO)CC1=CN=CN1C	2292.6	Semi standard non polar	33892256
Isopilocarpinic acid,1TBDMS,isomer #2	CCC(C(=O)O[Si](C)(C)C(C)(C)C)C(CO)CC1=CN=CN1C	2147.0	Standard non polar	33892256
Isopilocarpinic acid,1TBDMS,isomer #2	CCC(C(=O)O[Si](C)(C)C(C)(C)C)C(CO)CC1=CN=CN1C	2713.5	Standard polar	33892256
Isopilocarpinic acid,2TBDMS,isomer #1	CCC(C(=O)O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)CC1=CN=CN1C	2514.1	Semi standard non polar	33892256
Isopilocarpinic acid,2TBDMS,isomer #1	CCC(C(=O)O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)CC1=CN=CN1C	2443.7	Standard non polar	33892256
Isopilocarpinic acid,2TBDMS,isomer #1	CCC(C(=O)O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)CC1=CN=CN1C	2552.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isopilocarpinic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9610000000-6171819e93fa7bf421fa	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isopilocarpinic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isopilocarpinic 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopilocarpinic acid 10V, Positive-QTOF	splash10-0a4i-0590000000-2728381eda5a9eef9b23	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopilocarpinic acid 20V, Positive-QTOF	splash10-0005-6920000000-cebc98bbc3a0bb7efa38	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopilocarpinic acid 40V, Positive-QTOF	splash10-0002-9400000000-b77e54967f331ad3f06e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopilocarpinic acid 10V, Negative-QTOF	splash10-03gi-2940000000-b5edc46f83135fbefb03	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopilocarpinic acid 20V, Negative-QTOF	splash10-03dj-3900000000-9fc6df8096888a969870	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopilocarpinic acid 40V, Negative-QTOF	splash10-0002-8900000000-5f503814c54892d7417f	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8166865

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9991283

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 Isopilocarpinic acid (HMDB0253672)

MOL for HMDB0253672 (Isopilocarpinic acid)

3D MOL for HMDB0253672 (Isopilocarpinic acid)

3D SDF for HMDB0253672 (Isopilocarpinic acid)

3D-SDF for HMDB0253672 (Isopilocarpinic acid)

PDB for HMDB0253672 (Isopilocarpinic acid)

3D PDB for HMDB0253672 (Isopilocarpinic acid)

SMILES for HMDB0253672 (Isopilocarpinic acid)

INCHI for HMDB0253672 (Isopilocarpinic acid)

Structure for HMDB0253672 (Isopilocarpinic acid)

3D Structure for HMDB0253672 (Isopilocarpinic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra