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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:36:57 UTC

Update Date

2021-09-26 22:52:13 UTC

HMDB ID

HMDB0244460

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline

Description

CRILVASTATIN belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. Based on a literature review a small amount of articles have been published on CRILVASTATIN. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1r-cis-3,3,5-trimethylcyclohexyl ester5-oxo-l-proline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline 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

HMDB0250536
     RDKit          3D
Crilvastatin
 41 42  0  0  0  0  0  0  0  0999 V2000
   -1.1077   -0.9573    2.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9253   -1.3323    0.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0609   -1.4647   -0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5111   -0.1459   -0.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130    0.0755    0.0017 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9322    0.1738   -0.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9345    0.0569   -1.8894 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2101    0.4039    0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5941   -0.7365    0.9990 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1028   -0.5127    1.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4843    0.0411   -0.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6629    0.1192   -0.5993 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2966    0.4540   -0.8433 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3898    1.0201   -0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8189    0.7282   -0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5727    0.6206   -1.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4190    1.9700    0.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0896   -0.4317    0.6797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1582   -1.5394    2.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9460    0.1247    2.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6226   -1.3435    3.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3402   -2.3584    1.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2178   -2.1487   -0.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6525   -1.9367   -1.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2946   -0.2203   -1.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1642    1.3207    0.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1191   -0.6893    2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4524   -1.6865    0.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3046    0.2218    1.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6308   -1.4562    1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2570    0.7344   -1.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3542    1.7170   -1.3616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0120    1.6636    0.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6105   -0.4034   -1.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6169    1.0198   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0826    1.3149   -2.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7176    2.7275   -0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6371    2.3479    1.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2799    1.6851    1.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9187   -1.0370    0.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5021   -0.1400    1.6829 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  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  4 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 18  2  1  0
 13  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
M  END


  Mrv1652309102123372D          

 18 19  0  0  0  0            999 V2000
    0.1067    7.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    6.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    6.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    7.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8612    6.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4739    7.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    4.7652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512    4.7652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693    3.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242    2.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492    2.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9341    1.5907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7041    3.0428    0.0000 N   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  1  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 13 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244460

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CC(CC(C)(C)C1)OC(=O)C1CCC(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C14H23NO3/c1-9-6-10(8-14(2,3)7-9)18-13(17)11-4-5-12(16)15-11/h9-11H,4-8H2,1-3H3,(H,15,16)

> <INCHI_KEY>
FXAAOALUHHXBSO-UHFFFAOYSA-N

> <FORMULA>
C14H23NO3

> <MOLECULAR_WEIGHT>
253.342

> <EXACT_MASS>
253.167793605

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
27.74387253198975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,3,5-trimethylcyclohexyl 5-oxopyrrolidine-2-carboxylate

> <ALOGPS_LOGP>
2.21

> <JCHEM_LOGP>
1.9295801980000002

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.50428972875722

> <JCHEM_PKA_STRONGEST_BASIC>
-2.2246536354531052

> <JCHEM_POLAR_SURFACE_AREA>
55.400000000000006

> <JCHEM_REFRACTIVITY>
67.4434

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,3,5-trimethylcyclohexyl 5-oxopyrrolidine-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250536
     RDKit          3D
Crilvastatin
 41 42  0  0  0  0  0  0  0  0999 V2000
   -1.1077   -0.9573    2.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9253   -1.3323    0.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0609   -1.4647   -0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5111   -0.1459   -0.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130    0.0755    0.0017 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9322    0.1738   -0.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9345    0.0569   -1.8894 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2101    0.4039    0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5941   -0.7365    0.9990 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1028   -0.5127    1.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4843    0.0411   -0.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6629    0.1192   -0.5993 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2966    0.4540   -0.8433 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3898    1.0201   -0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8189    0.7282   -0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5727    0.6206   -1.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4190    1.9700    0.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0896   -0.4317    0.6797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1582   -1.5394    2.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9460    0.1247    2.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6226   -1.3435    3.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3402   -2.3584    1.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2178   -2.1487   -0.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6525   -1.9367   -1.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2946   -0.2203   -1.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1642    1.3207    0.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1191   -0.6893    2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4524   -1.6865    0.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3046    0.2218    1.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6308   -1.4562    1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2570    0.7344   -1.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3542    1.7170   -1.3616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0120    1.6636    0.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6105   -0.4034   -1.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6169    1.0198   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0826    1.3149   -2.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7176    2.7275   -0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6371    2.3479    1.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2799    1.6851    1.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9187   -1.0370    0.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5021   -0.1400    1.6829 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  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  4 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 18  2  1  0
 13  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
M  END

HEADER    PROTEIN                                 10-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-21         0                                  
HETATM    1  C   UNK     0       0.199  13.515   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.134  12.745   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.134  11.205   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.468  10.435   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.802  11.205   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.802  12.745   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.468  13.515   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.341  12.799   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.618  14.051   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.468   8.895   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.802   8.125   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.136   8.895   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.802   6.585   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.556   5.680   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.032   4.215   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.572   4.215   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.477   2.969   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      -5.048   5.680   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6    2                                                       
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    4   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0250536
HETATM    1  C1  UNL     1      -1.108  -0.957   2.132  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.925  -1.332   0.912  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.061  -1.465  -0.292  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.511  -0.146  -0.710  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.713   0.076   0.002  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.932   0.174  -0.616  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.935   0.057  -1.889  1.00  0.00           O  
HETATM    8  C6  UNL     1       3.210   0.404   0.116  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.594  -0.737   0.999  1.00  0.00           C  
HETATM   10  C8  UNL     1       5.103  -0.513   1.157  1.00  0.00           C  
HETATM   11  C9  UNL     1       5.484   0.041  -0.170  1.00  0.00           C  
HETATM   12  O3  UNL     1       6.663   0.119  -0.599  1.00  0.00           O  
HETATM   13  N1  UNL     1       4.297   0.454  -0.843  1.00  0.00           N  
HETATM   14  C10 UNL     1      -1.390   1.020  -0.472  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.819   0.728  -0.204  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.573   0.621  -1.537  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.419   1.970   0.476  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.090  -0.432   0.680  1.00  0.00           C  
HETATM   19  H1  UNL     1      -0.158  -1.539   2.059  1.00  0.00           H  
HETATM   20  H2  UNL     1      -0.946   0.125   2.217  1.00  0.00           H  
HETATM   21  H3  UNL     1      -1.623  -1.344   3.050  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.340  -2.358   1.136  1.00  0.00           H  
HETATM   23  H5  UNL     1      -0.218  -2.149  -0.074  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.653  -1.937  -1.099  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.295  -0.220  -1.817  1.00  0.00           H  
HETATM   26  H8  UNL     1       3.164   1.321   0.738  1.00  0.00           H  
HETATM   27  H9  UNL     1       3.119  -0.689   2.009  1.00  0.00           H  
HETATM   28  H10 UNL     1       3.452  -1.686   0.485  1.00  0.00           H  
HETATM   29  H11 UNL     1       5.305   0.222   1.981  1.00  0.00           H  
HETATM   30  H12 UNL     1       5.631  -1.456   1.390  1.00  0.00           H  
HETATM   31  H13 UNL     1       4.257   0.734  -1.847  1.00  0.00           H  
HETATM   32  H14 UNL     1      -1.354   1.717  -1.362  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.012   1.664   0.376  1.00  0.00           H  
HETATM   34  H16 UNL     1      -3.611  -0.403  -1.908  1.00  0.00           H  
HETATM   35  H17 UNL     1      -4.617   1.020  -1.400  1.00  0.00           H  
HETATM   36  H18 UNL     1      -3.083   1.315  -2.238  1.00  0.00           H  
HETATM   37  H19 UNL     1      -3.718   2.728  -0.261  1.00  0.00           H  
HETATM   38  H20 UNL     1      -2.637   2.348   1.184  1.00  0.00           H  
HETATM   39  H21 UNL     1      -4.280   1.685   1.116  1.00  0.00           H  
HETATM   40  H22 UNL     1      -3.919  -1.037   0.208  1.00  0.00           H  
HETATM   41  H23 UNL     1      -3.502  -0.140   1.683  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   18   22
CONECT    3    4   23   24
CONECT    4    5   14   25
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9   13   26
CONECT    9   10   27   28
CONECT   10   11   29   30
CONECT   11   12   12   13
CONECT   13   31
CONECT   14   15   32   33
CONECT   15   16   17   18
CONECT   16   34   35   36
CONECT   17   37   38   39
CONECT   18   40   41
END

HMDB0250536
     RDKit          3D
Crilvastatin
 41 42  0  0  0  0  0  0  0  0999 V2000
   -1.1077   -0.9573    2.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9253   -1.3323    0.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0609   -1.4647   -0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5111   -0.1459   -0.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130    0.0755    0.0017 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9322    0.1738   -0.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9345    0.0569   -1.8894 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2101    0.4039    0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5941   -0.7365    0.9990 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1028   -0.5127    1.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4843    0.0411   -0.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6629    0.1192   -0.5993 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2966    0.4540   -0.8433 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3898    1.0201   -0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8189    0.7282   -0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5727    0.6206   -1.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4190    1.9700    0.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0896   -0.4317    0.6797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1582   -1.5394    2.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9460    0.1247    2.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6226   -1.3435    3.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3402   -2.3584    1.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2178   -2.1487   -0.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6525   -1.9367   -1.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2946   -0.2203   -1.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1642    1.3207    0.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1191   -0.6893    2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4524   -1.6865    0.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3046    0.2218    1.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6308   -1.4562    1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2570    0.7344   -1.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3542    1.7170   -1.3616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0120    1.6636    0.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6105   -0.4034   -1.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6169    1.0198   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0826    1.3149   -2.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7176    2.7275   -0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6371    2.3479    1.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2799    1.6851    1.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9187   -1.0370    0.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5021   -0.1400    1.6829 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  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  4 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 18  2  1  0
 13  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,3,5-Trimethylcyclohexyl 5-hydroxy-3,4-dihydro-2H-pyrrole-2-carboxylic acid	Generator

Chemical Formula

C₁₄H₂₃NO₃

Average Molecular Weight

253.342

Monoisotopic Molecular Weight

253.167793605

IUPAC Name

3,3,5-trimethylcyclohexyl 5-oxopyrrolidine-2-carboxylate

Traditional Name

3,3,5-trimethylcyclohexyl 5-oxopyrrolidine-2-carboxylate

CAS Registry Number

Not Available

SMILES

CC1CC(CC(C)(C)C1)OC(=O)C1CCC(=O)N1

InChI Identifier

InChI=1S/C14H23NO3/c1-9-6-10(8-14(2,3)7-9)18-13(17)11-4-5-12(16)15-11/h9-11H,4-8H2,1-3H3,(H,15,16)

InChI Key

FXAAOALUHHXBSO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
Proline or derivatives
Oxoproline
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
2-pyrrolidone
Pyrrolidone
Pyrrolidine
Carboxamide group
Carboxylic acid ester
Lactam
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
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	2.21	ALOGPS
logP	1.93	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.5	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	67.44 m³·mol⁻¹	ChemAxon
Polarizability	27.74 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	160.244	30932474
DeepCCS	[M-H]-	157.886	30932474
DeepCCS	[M-2H]-	190.772	30932474
DeepCCS	[M+Na]+	166.337	30932474
AllCCS	[M+H]+	162.9	32859911
AllCCS	[M+H-H2O]+	159.4	32859911
AllCCS	[M+NH4]+	166.1	32859911
AllCCS	[M+Na]+	167.0	32859911
AllCCS	[M-H]-	163.5	32859911
AllCCS	[M+Na-2H]-	163.9	32859911
AllCCS	[M+HCOO]-	164.5	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline,1TMS,isomer #1	CC1CC(OC(=O)C2CCC(=O)N2[Si](C)(C)C)CC(C)(C)C1	1985.0	Semi standard non polar	33892256
1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline,1TMS,isomer #1	CC1CC(OC(=O)C2CCC(=O)N2[Si](C)(C)C)CC(C)(C)C1	1988.1	Standard non polar	33892256
1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline,1TMS,isomer #1	CC1CC(OC(=O)C2CCC(=O)N2[Si](C)(C)C)CC(C)(C)C1	2325.0	Standard polar	33892256
1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline,1TBDMS,isomer #1	CC1CC(OC(=O)C2CCC(=O)N2[Si](C)(C)C(C)(C)C)CC(C)(C)C1	2198.0	Semi standard non polar	33892256
1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline,1TBDMS,isomer #1	CC1CC(OC(=O)C2CCC(=O)N2[Si](C)(C)C(C)(C)C)CC(C)(C)C1	2209.7	Standard non polar	33892256
1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline,1TBDMS,isomer #1	CC1CC(OC(=O)C2CCC(=O)N2[Si](C)(C)C(C)(C)C)CC(C)(C)C1	2449.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9100000000-03c5884e1c6c5466e0d3	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline 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 - 1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline 10V, Positive-QTOF	splash10-0udi-0690000000-f46c49373aece817fb51	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline 20V, Positive-QTOF	splash10-06si-9750000000-3d0c3d6c43e2fde9e9ae	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline 40V, Positive-QTOF	splash10-0ac0-9600000000-5a7cb24822b2cc06425b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline 10V, Negative-QTOF	splash10-0f96-0930000000-cb5a6c844aa713e2558d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline 20V, Negative-QTOF	splash10-056r-9700000000-5e987c19c0b5c41aa08e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline 40V, Negative-QTOF	splash10-0006-9100000000-daeaa3dc6a7aef699b8c	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

54728

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60724

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 1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline (HMDB0244460)

MOL for HMDB0244460 (1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline)

3D MOL for HMDB0244460 (1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline)

3D SDF for HMDB0244460 (1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline)

3D-SDF for HMDB0244460 (1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline)

PDB for HMDB0244460 (1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline)

3D PDB for HMDB0244460 (1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline)

SMILES for HMDB0244460 (1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline)

INCHI for HMDB0244460 (1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline)

Structure for HMDB0244460 (1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline)

3D Structure for HMDB0244460 (1R-cis-3,3,5-Trimethylcyclohexyl ester5-oxo-L-proline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra