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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:43:32 UTC

Update Date

2022-11-23 22:02:39 UTC

HMDB ID

HMDB0250630

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cyclo(L-His-L-Pro)

Description

Cyclo(-His-Pro) belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Cyclo(-His-Pro) is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Cyclo(l-his-l-pro) is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Cyclo(L-His-L-Pro) 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

HMDB0250630
     RDKit          3D
Cyclo(his-pro)
 31 33  0  0  0  0  0  0  0  0999 V2000
   -0.4639    2.2660   -1.1565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5863    1.4110   -0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6144    0.7805    0.2001 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5996   -0.5798    0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4779   -1.3998   -0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8694   -0.8349   -0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700    0.1389   -1.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6471    0.3481   -0.7492 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9729   -0.4658    0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870   -1.1798    0.5724 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7593   -1.1330    0.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8699   -2.3968    0.8592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9393   -0.4054    0.5349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3515   -0.7893    0.4604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1016    0.5170    0.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0633    1.3375   -0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8463    1.0360    0.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    1.2726    0.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0120   -0.6371    1.7446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0756   -1.4121   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5663   -2.4315    0.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8532    0.6669   -1.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3374    1.0304   -1.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9328   -0.5571    0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6619   -1.3251    1.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5529   -1.3786   -0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2842    1.0205    1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0282    0.3904   -0.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3127    2.3976   -0.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9326    0.8524   -1.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0056    1.4600    1.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 10  6  1  0
 17 13  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 14 25  1  0
 14 26  1  0
 15 27  1  0
 15 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
M  END


  Mrv1533004231515072D          

 17 19  0  0  0  0            999 V2000
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5086    0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3155    0.9920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7280    0.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760   -0.3356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  6 10  1  0  0  0  0
  4 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  1  0  0  0  0
  2 17  1  0  0  0  0
 13 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250630

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1NC(CC2=CNC=N2)C(=O)N2CCCC12

> <INCHI_IDENTIFIER>
InChI=1S/C11H14N4O2/c16-10-9-2-1-3-15(9)11(17)8(14-10)4-7-5-12-6-13-7/h5-6,8-9H,1-4H2,(H,12,13)(H,14,16)

> <INCHI_KEY>
NAKUGCPAQTUSBE-UHFFFAOYSA-N

> <FORMULA>
C11H14N4O2

> <MOLECULAR_WEIGHT>
234.259

> <EXACT_MASS>
234.111675707

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
22.96625216126994

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(1H-imidazol-4-yl)methyl]-octahydropyrrolo[1,2-a]piperazine-1,4-dione

> <ALOGPS_LOGP>
-0.63

> <JCHEM_LOGP>
-1.2326926506666664

> <ALOGPS_LOGS>
-1.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.102490511434588

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.862808111431075

> <JCHEM_PKA_STRONGEST_BASIC>
6.533958610018198

> <JCHEM_POLAR_SURFACE_AREA>
78.08999999999999

> <JCHEM_REFRACTIVITY>
59.27990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(1H-imidazol-4-ylmethyl)-hexahydropyrrolo[1,2-a]piperazine-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250630
     RDKit          3D
Cyclo(his-pro)
 31 33  0  0  0  0  0  0  0  0999 V2000
   -0.4639    2.2660   -1.1565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5863    1.4110   -0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6144    0.7805    0.2001 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5996   -0.5798    0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4779   -1.3998   -0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8694   -0.8349   -0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700    0.1389   -1.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6471    0.3481   -0.7492 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9729   -0.4658    0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870   -1.1798    0.5724 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7593   -1.1330    0.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8699   -2.3968    0.8592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9393   -0.4054    0.5349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3515   -0.7893    0.4604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1016    0.5170    0.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0633    1.3375   -0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8463    1.0360    0.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    1.2726    0.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0120   -0.6371    1.7446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0756   -1.4121   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5663   -2.4315    0.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8532    0.6669   -1.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3374    1.0304   -1.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9328   -0.5571    0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6619   -1.3251    1.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5529   -1.3786   -0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2842    1.0205    1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0282    0.3904   -0.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3127    2.3976   -0.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9326    0.8524   -1.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0056    1.4600    1.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 10  6  1  0
 17 13  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 14 25  1  0
 14 26  1  0
 15 27  1  0
 15 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
M  END

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       7.454   1.540   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.122  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.283   1.532   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      11.789   1.852   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      12.559   0.518   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      11.529  -0.626   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0       4.787   0.000   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6                                                       
CONECT   11    4   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    2   13                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0250630
HETATM    1  O1  UNL     1      -0.464   2.266  -1.157  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.586   1.411  -0.238  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.614   0.780   0.200  1.00  0.00           N  
HETATM    4  C2  UNL     1       0.600  -0.580   0.733  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.478  -1.400  -0.215  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.869  -0.835  -0.231  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.370   0.139  -1.067  1.00  0.00           C  
HETATM    8  N2  UNL     1       4.647   0.348  -0.749  1.00  0.00           N  
HETATM    9  C6  UNL     1       4.973  -0.466   0.265  1.00  0.00           C  
HETATM   10  N3  UNL     1       3.887  -1.180   0.572  1.00  0.00           N  
HETATM   11  C7  UNL     1      -0.759  -1.133   0.708  1.00  0.00           C  
HETATM   12  O2  UNL     1      -0.870  -2.397   0.859  1.00  0.00           O  
HETATM   13  N4  UNL     1      -1.939  -0.405   0.535  1.00  0.00           N  
HETATM   14  C8  UNL     1      -3.352  -0.789   0.460  1.00  0.00           C  
HETATM   15  C9  UNL     1      -4.102   0.517   0.291  1.00  0.00           C  
HETATM   16  C10 UNL     1      -3.063   1.338  -0.451  1.00  0.00           C  
HETATM   17  C11 UNL     1      -1.846   1.036   0.390  1.00  0.00           C  
HETATM   18  H1  UNL     1       1.544   1.273   0.153  1.00  0.00           H  
HETATM   19  H2  UNL     1       1.012  -0.637   1.745  1.00  0.00           H  
HETATM   20  H3  UNL     1       1.076  -1.412  -1.231  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.566  -2.432   0.159  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.853   0.667  -1.855  1.00  0.00           H  
HETATM   23  H6  UNL     1       5.337   1.030  -1.190  1.00  0.00           H  
HETATM   24  H7  UNL     1       5.933  -0.557   0.772  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.662  -1.325   1.370  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.553  -1.379  -0.478  1.00  0.00           H  
HETATM   27  H10 UNL     1      -4.284   1.021   1.257  1.00  0.00           H  
HETATM   28  H11 UNL     1      -5.028   0.390  -0.301  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.313   2.398  -0.511  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.933   0.852  -1.444  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.006   1.460   1.401  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   17
CONECT    3    4   18
CONECT    4    5   11   19
CONECT    5    6   20   21
CONECT    6    7    7   10
CONECT    7    8   22
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   11   12   12   13
CONECT   13   14   17
CONECT   14   15   25   26
CONECT   15   16   27   28
CONECT   16   17   29   30
CONECT   17   31
END

HMDB0250630
     RDKit          3D
Cyclo(his-pro)
 31 33  0  0  0  0  0  0  0  0999 V2000
   -0.4639    2.2660   -1.1565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5863    1.4110   -0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6144    0.7805    0.2001 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5996   -0.5798    0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4779   -1.3998   -0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8694   -0.8349   -0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700    0.1389   -1.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6471    0.3481   -0.7492 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9729   -0.4658    0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870   -1.1798    0.5724 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7593   -1.1330    0.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8699   -2.3968    0.8592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9393   -0.4054    0.5349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3515   -0.7893    0.4604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1016    0.5170    0.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0633    1.3375   -0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8463    1.0360    0.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    1.2726    0.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0120   -0.6371    1.7446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0756   -1.4121   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5663   -2.4315    0.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8532    0.6669   -1.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3374    1.0304   -1.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9328   -0.5571    0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6619   -1.3251    1.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5529   -1.3786   -0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2842    1.0205    1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0282    0.3904   -0.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3127    2.3976   -0.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9326    0.8524   -1.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0056    1.4600    1.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 10  6  1  0
 17 13  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 14 25  1  0
 14 26  1  0
 15 27  1  0
 15 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₁H₁₄N₄O₂

Average Molecular Weight

234.259

Monoisotopic Molecular Weight

234.111675707

IUPAC Name

3-[(1H-imidazol-4-yl)methyl]-octahydropyrrolo[1,2-a]piperazine-1,4-dione

Traditional Name

3-(1H-imidazol-4-ylmethyl)-hexahydropyrrolo[1,2-a]piperazine-1,4-dione

CAS Registry Number

Not Available

SMILES

O=C1NC(CC2=CNC=N2)C(=O)N2CCCC12

InChI Identifier

InChI=1S/C11H14N4O2/c16-10-9-2-1-3-15(9)11(17)8(14-10)4-7-5-12-6-13-7/h5-6,8-9H,1-4H2,(H,12,13)(H,14,16)

InChI Key

NAKUGCPAQTUSBE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

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 acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Dioxopiperazine
2,5-dioxopiperazine
N-alkylpiperazine
1,4-diazinane
Piperazine
Azole
Imidazole
Pyrrolidine
Tertiary carboxylic acid amide
Heteroaromatic compound
Lactam
Secondary carboxylic acid amide
Carboxamide group
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

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	-0.63	ALOGPS
logP	-1.2	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	10.86	ChemAxon
pKa (Strongest Basic)	6.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	78.09 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	59.28 m³·mol⁻¹	ChemAxon
Polarizability	22.97 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	184.303	30932474
DeepCCS	[M+Na]+	159.283	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	8.8888 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.16 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	516.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	236.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	84.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	160.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	49.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	252.7 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	262.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	778.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	579.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	48.1 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	762.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	176.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	191.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	523.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	563.5 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	245.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyclo(his-pro)	O=C1NC(CC2=CNC=N2)C(=O)N2CCCC12	3343.2	Standard polar	33892256
Cyclo(his-pro)	O=C1NC(CC2=CNC=N2)C(=O)N2CCCC12	2378.0	Standard non polar	33892256
Cyclo(his-pro)	O=C1NC(CC2=CNC=N2)C(=O)N2CCCC12	2750.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cyclo(his-pro),1TMS,isomer #1	C[Si](C)(C)N1C(=O)C2CCCN2C(=O)C1CC1=C[NH]C=N1	2327.4	Semi standard non polar	33892256
Cyclo(his-pro),1TMS,isomer #1	C[Si](C)(C)N1C(=O)C2CCCN2C(=O)C1CC1=C[NH]C=N1	2373.2	Standard non polar	33892256
Cyclo(his-pro),1TMS,isomer #1	C[Si](C)(C)N1C(=O)C2CCCN2C(=O)C1CC1=C[NH]C=N1	3347.0	Standard polar	33892256
Cyclo(his-pro),1TMS,isomer #2	C[Si](C)(C)N1C=NC(CC2NC(=O)C3CCCN3C2=O)=C1	2564.5	Semi standard non polar	33892256
Cyclo(his-pro),1TMS,isomer #2	C[Si](C)(C)N1C=NC(CC2NC(=O)C3CCCN3C2=O)=C1	2463.5	Standard non polar	33892256
Cyclo(his-pro),1TMS,isomer #2	C[Si](C)(C)N1C=NC(CC2NC(=O)C3CCCN3C2=O)=C1	3798.3	Standard polar	33892256
Cyclo(his-pro),2TMS,isomer #1	C[Si](C)(C)N1C(=O)C2CCCN2C(=O)C1CC1=CN([Si](C)(C)C)C=N1	2423.8	Semi standard non polar	33892256
Cyclo(his-pro),2TMS,isomer #1	C[Si](C)(C)N1C(=O)C2CCCN2C(=O)C1CC1=CN([Si](C)(C)C)C=N1	2444.4	Standard non polar	33892256
Cyclo(his-pro),2TMS,isomer #1	C[Si](C)(C)N1C(=O)C2CCCN2C(=O)C1CC1=CN([Si](C)(C)C)C=N1	3241.1	Standard polar	33892256
Cyclo(his-pro),1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C2CCCN2C(=O)C1CC1=C[NH]C=N1	2570.1	Semi standard non polar	33892256
Cyclo(his-pro),1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C2CCCN2C(=O)C1CC1=C[NH]C=N1	2617.2	Standard non polar	33892256
Cyclo(his-pro),1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C2CCCN2C(=O)C1CC1=C[NH]C=N1	3496.1	Standard polar	33892256
Cyclo(his-pro),1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NC(CC2NC(=O)C3CCCN3C2=O)=C1	2804.5	Semi standard non polar	33892256
Cyclo(his-pro),1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NC(CC2NC(=O)C3CCCN3C2=O)=C1	2675.6	Standard non polar	33892256
Cyclo(his-pro),1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NC(CC2NC(=O)C3CCCN3C2=O)=C1	3900.6	Standard polar	33892256
Cyclo(his-pro),2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C2CCCN2C(=O)C1CC1=CN([Si](C)(C)C(C)(C)C)C=N1	2878.2	Semi standard non polar	33892256
Cyclo(his-pro),2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C2CCCN2C(=O)C1CC1=CN([Si](C)(C)C(C)(C)C)C=N1	2885.4	Standard non polar	33892256
Cyclo(his-pro),2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C2CCCN2C(=O)C1CC1=CN([Si](C)(C)C(C)(C)C)C=N1	3365.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclo(L-His-L-Pro) GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9520000000-499cebb55c1b01c5eb60	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclo(L-His-L-Pro) 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 - Cyclo(L-His-L-Pro) 10V, Positive-QTOF	splash10-000i-0090000000-6c3733b067abc1f8448a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclo(L-His-L-Pro) 20V, Positive-QTOF	splash10-000i-0090000000-ce4cc1393b84c40bde89	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclo(L-His-L-Pro) 40V, Positive-QTOF	splash10-006y-9500000000-4f26936037b645ba56ea	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclo(L-His-L-Pro) 10V, Negative-QTOF	splash10-001i-0090000000-ff13ab5a85d1c7537c9a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclo(L-His-L-Pro) 20V, Negative-QTOF	splash10-001i-3790000000-628059c8b9ea3113357d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclo(L-His-L-Pro) 40V, Negative-QTOF	splash10-0006-9400000000-3dca821bbf60b3971f71	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

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

Biospecimen	Status	Value	Age	Sex	Condition	Reference	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

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

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

3085031

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 Cyclo(L-His-L-Pro) (HMDB0250630)

MOL for HMDB0250630 (Cyclo(L-His-L-Pro))

3D MOL for HMDB0250630 (Cyclo(L-His-L-Pro))

3D SDF for HMDB0250630 (Cyclo(L-His-L-Pro))

3D-SDF for HMDB0250630 (Cyclo(L-His-L-Pro))

PDB for HMDB0250630 (Cyclo(L-His-L-Pro))

3D PDB for HMDB0250630 (Cyclo(L-His-L-Pro))

SMILES for HMDB0250630 (Cyclo(L-His-L-Pro))

INCHI for HMDB0250630 (Cyclo(L-His-L-Pro))

Structure for HMDB0250630 (Cyclo(L-His-L-Pro))

3D Structure for HMDB0250630 (Cyclo(L-His-L-Pro))

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra