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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-07 08:58:50 UTC

Update Date

2021-09-26 22:50:28 UTC

HMDB ID

HMDB0242741

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid

Description

(2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review very few articles have been published on (2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). (2r,4s)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic 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

HMDB0242741
     RDKit          3D
(2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid
 42 43  0  0  0  0  0  0  0  0999 V2000
    4.2120    0.2950   -1.5026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7637    0.5108   -0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7485    1.9586    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7682   -0.2110    0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5094   -0.1225    0.1210 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3738    0.1955   -0.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591    1.0950   -1.4702 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1548   -0.4856   -0.3183 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1067   -0.2467   -0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1618   -0.8628   -0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2821    0.0622    0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5772   -0.2622   -0.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6444    0.5980   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4453    1.8239    0.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1800    2.1766    0.9176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1153    1.3121    0.7221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4358   -1.2337    1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0384   -1.5281    0.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0380   -2.8570    0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1118   -3.8674    0.7849 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2636   -3.0813   -1.3033 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3291    0.1377   -1.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9709    1.1442   -2.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7329   -0.6093   -1.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7279    2.3964    0.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1808    2.0910    1.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3822    2.5601   -0.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3568   -0.3533    1.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9148   -1.2263    0.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7210    0.3384    0.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1560   -0.7155   -1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3478    0.8183   -1.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5555   -1.7833   -0.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7268   -1.2273   -0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6612    0.3484   -0.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2602    2.5110    0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0082    3.1505    1.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1094    1.5870    1.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3589   -0.4037    1.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8371   -2.1530    1.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7200   -1.4816    1.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -2.3989   -1.8317 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
  2  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
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18  8  1  0
 16 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 21 42  1  0
M  END


  Mrv1652309072111092D          

 21 22  0  0  0  0            999 V2000
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7376   -1.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9091   -0.6605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3507   -2.0195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4324   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9173   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5817   -4.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7613   -4.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242741

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(C)OC(=O)N1CC(CC1C(O)=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H21NO4/c1-16(2,3)21-15(20)17-10-12(9-13(17)14(18)19)11-7-5-4-6-8-11/h4-8,12-13H,9-10H2,1-3H3,(H,18,19)

> <INCHI_KEY>
JDAQDIQHICLYKH-UHFFFAOYSA-N

> <FORMULA>
C16H21NO4

> <MOLECULAR_WEIGHT>
291.347

> <EXACT_MASS>
291.14705816

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.375596688048716

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(tert-butoxy)carbonyl]-4-phenylpyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
2.684828448666667

> <ALOGPS_LOGS>
-2.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.045786427925054

> <JCHEM_POLAR_SURFACE_AREA>
66.84

> <JCHEM_REFRACTIVITY>
77.62600000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242741
     RDKit          3D
(2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid
 42 43  0  0  0  0  0  0  0  0999 V2000
    4.2120    0.2950   -1.5026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7637    0.5108   -0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7485    1.9586    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7682   -0.2110    0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5094   -0.1225    0.1210 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3738    0.1955   -0.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591    1.0950   -1.4702 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1548   -0.4856   -0.3183 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1067   -0.2467   -0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1618   -0.8628   -0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2821    0.0622    0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5772   -0.2622   -0.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6444    0.5980   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4453    1.8239    0.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1800    2.1766    0.9176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1153    1.3121    0.7221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4358   -1.2337    1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0384   -1.5281    0.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0380   -2.8570    0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1118   -3.8674    0.7849 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2636   -3.0813   -1.3033 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3291    0.1377   -1.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9709    1.1442   -2.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7329   -0.6093   -1.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7279    2.3964    0.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1808    2.0910    1.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3822    2.5601   -0.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3568   -0.3533    1.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9148   -1.2263    0.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7210    0.3384    0.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1560   -0.7155   -1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3478    0.8183   -1.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5555   -1.7833   -0.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7268   -1.2273   -0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6612    0.3484   -0.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2602    2.5110    0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0082    3.1505    1.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1094    1.5870    1.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3589   -0.4037    1.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8371   -2.1530    1.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7200   -1.4816    1.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -2.3989   -1.8317 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
  2  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
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18  8  1  0
 16 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 21 42  1  0
M  END

HEADER    PROTEIN                                 07-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-21         0                                  
HETATM    1  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.540   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.580  -3.215   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.104  -4.680   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.088  -3.215   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.377  -2.739   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.697  -1.233   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -2.521  -3.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.009  -5.926   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.540  -5.765   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.446  -7.011   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.819  -8.417   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.288  -8.578   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.382  -7.333   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11    8   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0242741
HETATM    1  C1  UNL     1       4.212   0.295  -1.503  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.764   0.511  -0.090  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.748   1.959   0.312  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.768  -0.211   0.811  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.509  -0.123   0.121  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.374   0.196  -0.590  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.459   1.095  -1.470  1.00  0.00           O  
HETATM    8  N1  UNL     1       0.155  -0.486  -0.318  1.00  0.00           N  
HETATM    9  C6  UNL     1      -1.107  -0.247  -0.992  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.162  -0.863  -0.072  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.282   0.062   0.141  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.577  -0.262  -0.229  1.00  0.00           C  
HETATM   13  C10 UNL     1      -5.644   0.598  -0.036  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.445   1.824   0.540  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.180   2.177   0.918  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.115   1.312   0.722  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.436  -1.234   1.196  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.038  -1.528   0.670  1.00  0.00           C  
HETATM   19  C16 UNL     1       0.038  -2.857   0.045  1.00  0.00           C  
HETATM   20  O3  UNL     1      -0.112  -3.867   0.785  1.00  0.00           O  
HETATM   21  O4  UNL     1       0.264  -3.081  -1.303  1.00  0.00           O  
HETATM   22  H1  UNL     1       5.329   0.138  -1.519  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.971   1.144  -2.159  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.733  -0.609  -1.898  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.728   2.396   0.271  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.181   2.091   1.325  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.382   2.560  -0.383  1.00  0.00           H  
HETATM   28  H7  UNL     1       4.357  -0.353   1.831  1.00  0.00           H  
HETATM   29  H8  UNL     1       4.915  -1.226   0.378  1.00  0.00           H  
HETATM   30  H9  UNL     1       5.721   0.338   0.828  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.156  -0.716  -1.985  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.348   0.818  -1.101  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.556  -1.783  -0.547  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.727  -1.227  -0.681  1.00  0.00           H  
HETATM   35  H14 UNL     1      -6.661   0.348  -0.324  1.00  0.00           H  
HETATM   36  H15 UNL     1      -6.260   2.511   0.701  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.008   3.150   1.378  1.00  0.00           H  
HETATM   38  H17 UNL     1      -2.109   1.587   1.020  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.359  -0.404   1.919  1.00  0.00           H  
HETATM   40  H19 UNL     1      -1.837  -2.153   1.654  1.00  0.00           H  
HETATM   41  H20 UNL     1       0.720  -1.482   1.466  1.00  0.00           H  
HETATM   42  H21 UNL     1       0.793  -2.399  -1.832  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4    5
CONECT    3   25   26   27
CONECT    4   28   29   30
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9   18
CONECT    9   10   31   32
CONECT   10   11   17   33
CONECT   11   12   12   16
CONECT   12   13   34
CONECT   13   14   14   35
CONECT   14   15   36
CONECT   15   16   16   37
CONECT   16   38
CONECT   17   18   39   40
CONECT   18   19   41
CONECT   19   20   20   21
CONECT   21   42
END

HMDB0242741
     RDKit          3D
(2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid
 42 43  0  0  0  0  0  0  0  0999 V2000
    4.2120    0.2950   -1.5026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7637    0.5108   -0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7485    1.9586    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7682   -0.2110    0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5094   -0.1225    0.1210 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3738    0.1955   -0.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591    1.0950   -1.4702 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1548   -0.4856   -0.3183 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1067   -0.2467   -0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1618   -0.8628   -0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2821    0.0622    0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5772   -0.2622   -0.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6444    0.5980   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4453    1.8239    0.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1800    2.1766    0.9176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1153    1.3121    0.7221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4358   -1.2337    1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0384   -1.5281    0.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0380   -2.8570    0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1118   -3.8674    0.7849 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2636   -3.0813   -1.3033 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3291    0.1377   -1.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9709    1.1442   -2.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7329   -0.6093   -1.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7279    2.3964    0.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1808    2.0910    1.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3822    2.5601   -0.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3568   -0.3533    1.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9148   -1.2263    0.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7210    0.3384    0.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1560   -0.7155   -1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3478    0.8183   -1.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5555   -1.7833   -0.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7268   -1.2273   -0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6612    0.3484   -0.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2602    2.5110    0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0082    3.1505    1.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1094    1.5870    1.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3589   -0.4037    1.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8371   -2.1530    1.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7200   -1.4816    1.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -2.3989   -1.8317 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
  2  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
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18  8  1  0
 16 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 21 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylate	Generator

Chemical Formula

C₁₆H₂₁NO₄

Average Molecular Weight

291.347

Monoisotopic Molecular Weight

291.14705816

IUPAC Name

1-[(tert-butoxy)carbonyl]-4-phenylpyrrolidine-2-carboxylic acid

Traditional Name

1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(C)(C)OC(=O)N1CC(CC1C(O)=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H21NO4/c1-16(2,3)21-15(20)17-10-12(9-13(17)14(18)19)11-7-5-4-6-8-11/h4-8,12-13H,9-10H2,1-3H3,(H,18,19)

InChI Key

JDAQDIQHICLYKH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Proline and derivatives

Alternative Parents

Substituents

Proline or derivatives
3-phenylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Monocyclic benzene moiety
Benzenoid
Pyrrole
Pyrrolidine
Carbamic acid ester
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
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	2.69	ALOGPS
logP	2.68	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	4.05	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.84 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	77.63 m³·mol⁻¹	ChemAxon
Polarizability	31.38 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]+	168.188	30932474
DeepCCS	[M-H]-	165.83	30932474
DeepCCS	[M-2H]-	198.715	30932474
DeepCCS	[M+Na]+	174.281	30932474
AllCCS	[M+H]+	167.6	32859911
AllCCS	[M+H-H2O]+	164.2	32859911
AllCCS	[M+NH4]+	170.6	32859911
AllCCS	[M+Na]+	171.5	32859911
AllCCS	[M-H]-	173.0	32859911
AllCCS	[M+Na-2H]-	173.1	32859911
AllCCS	[M+HCOO]-	173.4	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.	5.77 minutes	32390414
Predicted by Siyang on May 30, 2022	14.9172 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.71 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2376.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	371.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	178.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	186.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	135.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	707.9 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	736.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	69.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1170.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	497.2 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	1675.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	407.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	435.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	258.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	218.1 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	9.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid	CC(C)(C)OC(=O)N1CC(CC1C(O)=O)C1=CC=CC=C1	3072.2	Standard polar	33892256
(2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid	CC(C)(C)OC(=O)N1CC(CC1C(O)=O)C1=CC=CC=C1	1889.0	Standard non polar	33892256
(2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid	CC(C)(C)OC(=O)N1CC(CC1C(O)=O)C1=CC=CC=C1	2138.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-7960000000-7728eadc2070a4124c59	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid GC-MS (TBDMS_1_1) - 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 - (2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid 10V, Positive-QTOF	splash10-0006-0490000000-2b6cc795f08b0c722cf1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid 20V, Positive-QTOF	splash10-05tg-1930000000-e6cc22a185b6c504f482	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid 40V, Positive-QTOF	splash10-0a4l-2900000000-a3e2d40ba6211b355805	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid 10V, Negative-QTOF	splash10-0006-0390000000-edd7181ca0b4a543f71f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid 20V, Negative-QTOF	splash10-0006-0930000000-533e7a38b26df0e4194e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid 40V, Negative-QTOF	splash10-0006-3900000000-84762124db50a39b6271	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

3899865

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4712506

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 (2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid (HMDB0242741)

MOL for HMDB0242741 ((2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid)

3D MOL for HMDB0242741 ((2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid)

3D SDF for HMDB0242741 ((2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid)

3D-SDF for HMDB0242741 ((2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid)

PDB for HMDB0242741 ((2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid)

3D PDB for HMDB0242741 ((2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid)

SMILES for HMDB0242741 ((2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid)

INCHI for HMDB0242741 ((2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid)

Structure for HMDB0242741 ((2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid)

3D Structure for HMDB0242741 ((2R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra