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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2017-08-01 02:12:29 UTC

Update Date

2022-09-22 18:34:30 UTC

HMDB ID

HMDB0094651

Secondary Accession Numbers

HMDB94651

Metabolite Identification

Common Name

Pyroglutamylvaline

Description

pyroglutamylvaline, also known as pyro-glu-val or 5-oxoprolylvaline, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. pyroglutamylvaline is an extremely weak basic (essentially neutral) compound (based on its pKa). A dipeptide obtained by formal condensation of the carboxy group of pyroglutamic acid with the amino group of valine.

Structure

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

HMDB0094651
     RDKit          3D
Pyroglutamylvaline
 32 32  0  0  0  0  0  0  0  0999 V2000
    3.7988   -0.8592    0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5697   -0.0906    0.5513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7035    1.3214    0.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2996   -0.7545    0.0684 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1223   -0.0014    0.4433 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7851    0.4980   -0.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5462    0.2741   -1.7772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9903    1.2671   -0.2097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9286    0.3294    0.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2348    0.3647   -0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8318    0.8113   -1.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4352    0.4834   -2.6284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6955    1.6292   -1.4073 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2057   -2.0786    0.7351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2575   -2.3978    1.4631 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2397   -2.9770    0.5147 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6899   -0.1804    0.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1089   -1.5969    0.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6956   -1.3974   -0.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5178   -0.0909    1.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6491    2.0747    0.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7229    1.4910   -0.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9333    1.5537   -0.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3224   -0.8376   -1.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1160    0.2083    1.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7637    2.1699    0.3921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5537   -0.7226    0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9928    0.6509    1.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6963   -0.6378   -0.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9532    1.0855    0.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4161    2.3872   -2.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1026   -3.9770    0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  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  2  0
 14 16  1  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  6
  5 25  1  0
  8 26  1  1
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 13 31  1  0
 16 32  1  0
M  END

      
  Mrv1652311301723442D          

 16 16  0  0  0  0            999 V2000
 2499.9876 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7016 2499.5877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4176 2500.0010    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2502.1317 2499.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.8457 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1317 2498.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4176 2500.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1317 2501.2366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7016 2501.2366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9876 2500.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.1542 2499.8434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.6039 2500.0821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2497.9364 2499.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.1914 2498.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.0164 2498.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2713 2499.5971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  6  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  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
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 13 11  2  0  0  0  0
 16  1  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0094651

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N2O4/c1-5(2)8(10(15)16)12-9(14)6-3-4-7(13)11-6/h5-6,8H,3-4H2,1-2H3,(H,11,13)(H,12,14)(H,15,16)/t6-,8-/m0/s1

> <INCHI_KEY>
DTSWLLBBGHRXQH-XPUUQOCRSA-N

> <FORMULA>
C10H16N2O4

> <MOLECULAR_WEIGHT>
228.248

> <EXACT_MASS>
228.111007003

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
22.442916225445618

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-3-methyl-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}butanoic acid

> <ALOGPS_LOGP>
-0.44

> <JCHEM_LOGP>
-0.5386934783333334

> <ALOGPS_LOGS>
-1.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.453723736859612

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8622234295377345

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1834074151100813

> <JCHEM_POLAR_SURFACE_AREA>
95.5

> <JCHEM_REFRACTIVITY>
54.3808

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-methyl-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0094651
     RDKit          3D
Pyroglutamylvaline
 32 32  0  0  0  0  0  0  0  0999 V2000
    3.7988   -0.8592    0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5697   -0.0906    0.5513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7035    1.3214    0.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2996   -0.7545    0.0684 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1223   -0.0014    0.4433 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7851    0.4980   -0.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5462    0.2741   -1.7772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9903    1.2671   -0.2097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9286    0.3294    0.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2348    0.3647   -0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8318    0.8113   -1.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4352    0.4834   -2.6284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6955    1.6292   -1.4073 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2057   -2.0786    0.7351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2575   -2.3978    1.4631 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2397   -2.9770    0.5147 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6899   -0.1804    0.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1089   -1.5969    0.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6956   -1.3974   -0.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5178   -0.0909    1.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6491    2.0747    0.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7229    1.4910   -0.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9333    1.5537   -0.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3224   -0.8376   -1.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1160    0.2083    1.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7637    2.1699    0.3921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5537   -0.7226    0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9928    0.6509    1.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6963   -0.6378   -0.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9532    1.0855    0.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4161    2.3872   -2.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1026   -3.9770    0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  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  2  0
 14 16  1  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  6
  5 25  1  0
  8 26  1  1
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 13 31  1  0
 16 32  1  0
M  END

HEADER    PROTEIN                                 30-NOV-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-NOV-17         0                                  
HETATM    1  C   UNK     0    4666.6444666.669   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4667.9764665.897   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4669.3134666.669   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4670.6464665.897   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4671.9794666.669   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4670.6464664.358   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4669.3134668.208   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    4670.6464668.975   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    4667.9764668.975   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    4666.6444668.208   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    4661.3554666.374   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0    4664.0614666.820   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    4662.8154665.915   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4663.2914664.450   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4664.8314664.450   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4665.3064665.915   0.000  0.00  0.00           C+0
CONECT    1    2   10   16                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    1                                                            
CONECT   11   13                                                            
CONECT   12   13   16                                                       
CONECT   13   14   12   11                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12    1                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0094651
HETATM    1  C1  UNL     1       3.799  -0.859   0.170  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.570  -0.091   0.551  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.703   1.321   0.020  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.300  -0.755   0.068  1.00  0.00           C  
HETATM    5  N1  UNL     1       0.122  -0.001   0.443  1.00  0.00           N  
HETATM    6  C5  UNL     1      -0.785   0.498  -0.564  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.546   0.274  -1.777  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.990   1.267  -0.210  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.929   0.329   0.522  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.235   0.365  -0.200  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.832   0.811  -1.571  1.00  0.00           C  
HETATM   12  O2  UNL     1      -4.435   0.483  -2.628  1.00  0.00           O  
HETATM   13  N2  UNL     1      -2.695   1.629  -1.407  1.00  0.00           N  
HETATM   14  C10 UNL     1       1.206  -2.079   0.735  1.00  0.00           C  
HETATM   15  O3  UNL     1       0.258  -2.398   1.463  1.00  0.00           O  
HETATM   16  O4  UNL     1       2.240  -2.977   0.515  1.00  0.00           O  
HETATM   17  H1  UNL     1       4.690  -0.180   0.031  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.109  -1.597   0.924  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.696  -1.397  -0.800  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.518  -0.091   1.669  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.649   2.075   0.854  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.723   1.491  -0.435  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.933   1.554  -0.738  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.322  -0.838  -1.031  1.00  0.00           H  
HETATM   25  H9  UNL     1      -0.116   0.208   1.435  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.764   2.170   0.392  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.554  -0.723   0.521  1.00  0.00           H  
HETATM   28  H12 UNL     1      -2.993   0.651   1.574  1.00  0.00           H  
HETATM   29  H13 UNL     1      -4.696  -0.638  -0.228  1.00  0.00           H  
HETATM   30  H14 UNL     1      -4.953   1.086   0.260  1.00  0.00           H  
HETATM   31  H15 UNL     1      -2.416   2.387  -2.069  1.00  0.00           H  
HETATM   32  H16 UNL     1       2.103  -3.977   0.644  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4   20
CONECT    3   21   22   23
CONECT    4    5   14   24
CONECT    5    6   25
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   15   16
CONECT   16   32
END

HMDB0094651
     RDKit          3D
Pyroglutamylvaline
 32 32  0  0  0  0  0  0  0  0999 V2000
    3.7988   -0.8592    0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5697   -0.0906    0.5513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7035    1.3214    0.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2996   -0.7545    0.0684 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1223   -0.0014    0.4433 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7851    0.4980   -0.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5462    0.2741   -1.7772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9903    1.2671   -0.2097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9286    0.3294    0.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2348    0.3647   -0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8318    0.8113   -1.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4352    0.4834   -2.6284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6955    1.6292   -1.4073 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2057   -2.0786    0.7351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2575   -2.3978    1.4631 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2397   -2.9770    0.5147 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6899   -0.1804    0.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1089   -1.5969    0.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6956   -1.3974   -0.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5178   -0.0909    1.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6491    2.0747    0.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7229    1.4910   -0.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9333    1.5537   -0.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3224   -0.8376   -1.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1160    0.2083    1.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7637    2.1699    0.3921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5537   -0.7226    0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9928    0.6509    1.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6963   -0.6378   -0.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9532    1.0855    0.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4161    2.3872   -2.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1026   -3.9770    0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  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  2  0
 14 16  1  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  6
  5 25  1  0
  8 26  1  1
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 13 31  1  0
 16 32  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-Oxoprolylvaline	ChEBI
L-Pyroglutamyl-L-valine	ChEBI
p-Glu-val	ChEBI
Pyro-glu-val	ChEBI
Pyroglutamyl valine	ChEBI
N-(5-Oxo-L-prolyl)-L-valine	HMDB
N-(5-Oxo-L-prolyl)-valine	HMDB
5-Oxo-L-prolyl-L-valine	HMDB
L-Pyrrolidonecarboxyl-L-valine	HMDB
Pyrrolidin-2-one-5-carbonylvaline	HMDB
Pyroglutamylvaline	HMDB

Chemical Formula

C₁₀H₁₆N₂O₄

Average Molecular Weight

228.248

Monoisotopic Molecular Weight

228.111007003

IUPAC Name

(2S)-3-methyl-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}butanoic acid

Traditional Name

(2S)-3-methyl-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}butanoic acid

CAS Registry Number

21282-10-0

SMILES

CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1)C(O)=O

InChI Identifier

InChI=1S/C10H16N2O4/c1-5(2)8(10(15)16)12-9(14)6-3-4-7(13)11-6/h5-6,8H,3-4H2,1-2H3,(H,11,13)(H,12,14)(H,15,16)/t6-,8-/m0/s1

InChI Key

DTSWLLBBGHRXQH-XPUUQOCRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Valine or derivatives
Proline or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine-2-carboxamide
Branched fatty acid
Heterocyclic fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Pyrrolidone
2-pyrrolidone
Pyrrolidine
Secondary carboxylic acid amide
Carboxamide group
Lactam
Organoheterocyclic compound
Carboxylic acid
Azacycle
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Feces (PMID: 27275383)

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	-0.44	ALOGPS
logP	-0.54	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.86	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.5 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	54.38 m³·mol⁻¹	ChemAxon
Polarizability	22.44 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
DarkChem	[M+H]+	155.121	31661259
DarkChem	[M-H]-	150.596	31661259
DeepCCS	[M+H]+	154.088	30932474
DeepCCS	[M-H]-	151.73	30932474
DeepCCS	[M-2H]-	184.707	30932474
DeepCCS	[M+Na]+	160.181	30932474
AllCCS	[M+H]+	150.9	32859911
AllCCS	[M+H-H2O]+	147.3	32859911
AllCCS	[M+NH4]+	154.2	32859911
AllCCS	[M+Na]+	155.2	32859911
AllCCS	[M-H]-	151.7	32859911
AllCCS	[M+Na-2H]-	152.2	32859911
AllCCS	[M+HCOO]-	152.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pyroglutamylvaline	CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1)C(O)=O	3210.2	Standard polar	33892256
Pyroglutamylvaline	CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1)C(O)=O	2048.1	Standard non polar	33892256
Pyroglutamylvaline	CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1)C(O)=O	2185.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pyroglutamylvaline,1TMS,isomer #1	CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1)C(=O)O[Si](C)(C)C	2019.7	Semi standard non polar	33892256
Pyroglutamylvaline,1TMS,isomer #2	CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H]1CCC(=O)N1)[Si](C)(C)C	1966.5	Semi standard non polar	33892256
Pyroglutamylvaline,1TMS,isomer #3	CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C)C(=O)O	1963.6	Semi standard non polar	33892256
Pyroglutamylvaline,2TMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1)[Si](C)(C)C	2008.6	Semi standard non polar	33892256
Pyroglutamylvaline,2TMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1)[Si](C)(C)C	2006.9	Standard non polar	33892256
Pyroglutamylvaline,2TMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1)[Si](C)(C)C	3048.4	Standard polar	33892256
Pyroglutamylvaline,2TMS,isomer #2	CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C	1980.0	Semi standard non polar	33892256
Pyroglutamylvaline,2TMS,isomer #2	CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2017.9	Standard non polar	33892256
Pyroglutamylvaline,2TMS,isomer #2	CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C	2785.2	Standard polar	33892256
Pyroglutamylvaline,2TMS,isomer #3	CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C)[Si](C)(C)C	1895.7	Semi standard non polar	33892256
Pyroglutamylvaline,2TMS,isomer #3	CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C)[Si](C)(C)C	2016.5	Standard non polar	33892256
Pyroglutamylvaline,2TMS,isomer #3	CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C)[Si](C)(C)C	2665.4	Standard polar	33892256
Pyroglutamylvaline,3TMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C)[Si](C)(C)C	1960.5	Semi standard non polar	33892256
Pyroglutamylvaline,3TMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C)[Si](C)(C)C	2097.4	Standard non polar	33892256
Pyroglutamylvaline,3TMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C)[Si](C)(C)C	2352.6	Standard polar	33892256
Pyroglutamylvaline,1TBDMS,isomer #1	CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1)C(=O)O[Si](C)(C)C(C)(C)C	2246.6	Semi standard non polar	33892256
Pyroglutamylvaline,1TBDMS,isomer #2	CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H]1CCC(=O)N1)[Si](C)(C)C(C)(C)C	2216.2	Semi standard non polar	33892256
Pyroglutamylvaline,1TBDMS,isomer #3	CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C)C(=O)O	2198.0	Semi standard non polar	33892256
Pyroglutamylvaline,2TBDMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1)[Si](C)(C)C(C)(C)C	2452.1	Semi standard non polar	33892256
Pyroglutamylvaline,2TBDMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1)[Si](C)(C)C(C)(C)C	2422.6	Standard non polar	33892256
Pyroglutamylvaline,2TBDMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1)[Si](C)(C)C(C)(C)C	3031.4	Standard polar	33892256
Pyroglutamylvaline,2TBDMS,isomer #2	CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2434.7	Semi standard non polar	33892256
Pyroglutamylvaline,2TBDMS,isomer #2	CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2444.4	Standard non polar	33892256
Pyroglutamylvaline,2TBDMS,isomer #2	CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2816.0	Standard polar	33892256
Pyroglutamylvaline,2TBDMS,isomer #3	CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2382.2	Semi standard non polar	33892256
Pyroglutamylvaline,2TBDMS,isomer #3	CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2425.5	Standard non polar	33892256
Pyroglutamylvaline,2TBDMS,isomer #3	CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2755.2	Standard polar	33892256
Pyroglutamylvaline,3TBDMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2640.3	Semi standard non polar	33892256
Pyroglutamylvaline,3TBDMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2678.9	Standard non polar	33892256
Pyroglutamylvaline,3TBDMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2683.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pyroglutamylvaline GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-9200000000-9db84667672f6a505f45	2017-09-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyroglutamylvaline GC-MS (3 TMS) - 70eV, Positive	splash10-0a6r-6932300000-013d4bddc38160ccb236	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyroglutamylvaline 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 - Pyroglutamylvaline 10V, Negative-QTOF	splash10-0059-0490000000-c6f69f147e19e6d90c77	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 20V, Negative-QTOF	splash10-07yi-3950000000-bce5cc05c920b36b4fdc	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 40V, Negative-QTOF	splash10-00kf-9200000000-add672a776175abea58c	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 10V, Positive-QTOF	splash10-02cr-3690000000-3bd2cf60b4176dafefff	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 20V, Positive-QTOF	splash10-0089-9300000000-e0b20d2fcc43e6cb45e5	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 40V, Positive-QTOF	splash10-05gi-9100000000-987567c667aa950bbc60	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 10V, Positive-QTOF	splash10-03gi-4980000000-ca77ede8584ae5157107	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 20V, Positive-QTOF	splash10-001i-9100000000-9b083dd619db45b224bd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 40V, Positive-QTOF	splash10-001i-9300000000-bc014979775b6ec4a63e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 10V, Negative-QTOF	splash10-004i-0090000000-c8a3f11499151a4d3a87	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 20V, Negative-QTOF	splash10-004i-6900000000-fd52a1fe405d3f84c962	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 40V, Negative-QTOF	splash10-0006-9100000000-544465ead7a4ca8f9b9b	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

152416

PDB ID

Not Available

ChEBI ID

132991

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

Not Available

Showing metabocard for Pyroglutamylvaline (HMDB0094651)

MOL for HMDB0094651 (Pyroglutamylvaline)

3D MOL for HMDB0094651 (Pyroglutamylvaline)

3D SDF for HMDB0094651 (Pyroglutamylvaline)

3D-SDF for HMDB0094651 (Pyroglutamylvaline)

PDB for HMDB0094651 (Pyroglutamylvaline)

3D PDB for HMDB0094651 (Pyroglutamylvaline)

SMILES for HMDB0094651 (Pyroglutamylvaline)

INCHI for HMDB0094651 (Pyroglutamylvaline)

Structure for HMDB0094651 (Pyroglutamylvaline)

3D Structure for HMDB0094651 (Pyroglutamylvaline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra