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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:34 UTC

Update Date

2021-09-14 15:29:57 UTC

HMDB ID

HMDB0002053

Secondary Accession Numbers

HMDB02053

Metabolite Identification

Common Name

Histidylproline diketopiperazine

Description

Histidylproline diketopiperazine is a cyclic dipeptide initially described in both the hypothalamus and cerebral tissues, has been detected in various sites outside the central nervous system, including the gastrointestinal tract and, more specifically, the endocrine pancreas. Histidylproline diketopiperazine belongs to the family of Dioxopiperazines. These are compounds containing a piperazine ring bearing two ketone groups.

Structure

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

HMDB0002053
     RDKit          3D
Histidylproline diketopiperazine
 34 36  0  0  0  0  0  0  0  0999 V2000
    0.6450    2.5501    0.2899 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4613    1.3192    0.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7680    0.8044   -0.2003 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0398   -0.5894    0.0722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2603   -1.1353   -0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4369   -0.3684   -0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2071   -0.6393    1.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1899    0.2573    1.1610 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0697    1.1008    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0114    0.7267   -0.6176 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2036   -1.3320   -0.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215   -2.4296   -0.9288 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4777   -0.7792   -0.0226 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7233   -1.3701   -0.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6751   -0.3640   -1.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6934    0.9507   -0.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8599    1.0445    0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179    0.4053    0.7785 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4770    1.3471   -0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1758   -0.6532    1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2238   -1.1466   -1.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3718   -2.1859   -0.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0540   -1.4541    1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7380    1.9488   -0.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7315    1.2371   -1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2271   -1.9431    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5325   -2.1288   -1.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5380   -0.2439   -2.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7104   -0.8028   -0.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3450    1.7305   -1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7319    1.2815   -0.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    2.1263    1.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3926    0.6247    1.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2003    0.1106    1.8202 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  2  0
  9 10  1  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 18  1  0
 18  2  1  0
 10  6  1  0
 18 13  1  0
  3 19  1  0
  4 20  1  1
  5 21  1  0
  5 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 14 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  1
M  END


  Mrv0541 02231219202D          

 19 21  0  0  1  0            999 V2000
   14.6775  -12.5409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6775   -9.2410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3919  -11.3034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9629  -10.4785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7804  -11.6389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6409  -10.3115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3919  -10.4785    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.1293  -10.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1293  -11.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8769  -10.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8769  -11.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9629  -11.3034    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.6775  -11.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6775  -10.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2485  -11.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5340  -11.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4478  -10.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2284  -11.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3876   -9.5846    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  2  0  0  0  0
  2 14  2  0  0  0  0
  3  7  1  0  0  0  0
  3  9  1  0  0  0  0
  3 13  1  0  0  0  0
  4 12  1  0  0  0  0
  4 14  1  0  0  0  0
  5 16  1  0  0  0  0
  5 18  1  0  0  0  0
  6 17  1  0  0  0  0
  6 18  2  0  0  0  0
  7  8  1  0  0  0  0
  7 14  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 12 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  7 19  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0002053

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CCCCN1C(=O)[C@H](CC1=CN=CN1)NC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H16N4O2/c17-11-10-3-1-2-4-16(10)12(18)9(15-11)5-8-6-13-7-14-8/h6-7,9-10H,1-5H2,(H,13,14)(H,15,17)/t9-,10-/m0/s1

> <INCHI_KEY>
LCXWQHWWTPOAFI-UWVGGRQHSA-N

> <FORMULA>
C12H16N4O2

> <MOLECULAR_WEIGHT>
248.281

> <EXACT_MASS>
248.127325776

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.497180356804776

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,9aS)-3-(1H-imidazol-5-ylmethyl)-octahydro-1H-pyrido[1,2-a]piperazine-1,4-dione

> <ALOGPS_LOGP>
-0.36

> <JCHEM_LOGP>
-1.1266477496666663

> <ALOGPS_LOGS>
-1.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.9398846546521

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.947127840166175

> <JCHEM_PKA_STRONGEST_BASIC>
6.742948016045374

> <JCHEM_POLAR_SURFACE_AREA>
78.09

> <JCHEM_REFRACTIVITY>
64.44660000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,9aS)-3-(3H-imidazol-4-ylmethyl)-hexahydro-2H-pyrido[1,2-a]piperazine-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002053
     RDKit          3D
Histidylproline diketopiperazine
 34 36  0  0  0  0  0  0  0  0999 V2000
    0.6450    2.5501    0.2899 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4613    1.3192    0.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7680    0.8044   -0.2003 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0398   -0.5894    0.0722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2603   -1.1353   -0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4369   -0.3684   -0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2071   -0.6393    1.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1899    0.2573    1.1610 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0697    1.1008    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0114    0.7267   -0.6176 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2036   -1.3320   -0.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215   -2.4296   -0.9288 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4777   -0.7792   -0.0226 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7233   -1.3701   -0.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6751   -0.3640   -1.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6934    0.9507   -0.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8599    1.0445    0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179    0.4053    0.7785 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4770    1.3471   -0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1758   -0.6532    1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2238   -1.1466   -1.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3718   -2.1859   -0.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0540   -1.4541    1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7380    1.9488   -0.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7315    1.2371   -1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2271   -1.9431    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5325   -2.1288   -1.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5380   -0.2439   -2.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7104   -0.8028   -0.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3450    1.7305   -1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7319    1.2815   -0.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    2.1263    1.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3926    0.6247    1.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2003    0.1106    1.8202 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  2  0
  9 10  1  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 18  1  0
 18  2  1  0
 10  6  1  0
 18 13  1  0
  3 19  1  0
  4 20  1  1
  5 21  1  0
  5 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 14 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      27.398 -23.410   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      27.398 -17.250   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      28.731 -21.100   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      26.064 -19.560   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      21.990 -21.726   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      21.730 -19.248   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      28.731 -19.560   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.108 -18.736   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.108 -21.923   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      31.503 -19.528   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.503 -21.132   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.064 -21.100   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.398 -21.870   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.398 -18.790   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.731 -21.870   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      23.397 -21.100   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.236 -19.568   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.960 -20.582   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0      28.723 -17.891   0.000  0.00  0.00           H+0
CONECT    1   13                                                            
CONECT    2   14                                                            
CONECT    3    7    9   13                                                  
CONECT    4   12   14                                                       
CONECT    5   16   18                                                       
CONECT    6   17   18                                                       
CONECT    7    3    8   14   19                                             
CONECT    8    7   10                                                       
CONECT    9    3   11                                                       
CONECT   10    8   11                                                       
CONECT   11    9   10                                                       
CONECT   12    4   13   15                                                  
CONECT   13    1    3   12                                                  
CONECT   14    2    4    7                                                  
CONECT   15   12   16                                                       
CONECT   16    5   15   17                                                  
CONECT   17    6   16                                                       
CONECT   18    5    6                                                       
CONECT   19    7                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0002053
HETATM    1  O1  UNL     1       0.645   2.550   0.290  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.461   1.319   0.284  1.00  0.00           C  
HETATM    3  N1  UNL     1      -0.768   0.804  -0.200  1.00  0.00           N  
HETATM    4  C2  UNL     1      -1.040  -0.589   0.072  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.260  -1.135  -0.566  1.00  0.00           C  
HETATM    6  C4  UNL     1      -3.437  -0.368  -0.084  1.00  0.00           C  
HETATM    7  C5  UNL     1      -4.207  -0.639   1.040  1.00  0.00           C  
HETATM    8  N2  UNL     1      -5.190   0.257   1.161  1.00  0.00           N  
HETATM    9  C6  UNL     1      -5.070   1.101   0.138  1.00  0.00           C  
HETATM   10  N3  UNL     1      -4.011   0.727  -0.618  1.00  0.00           N  
HETATM   11  C7  UNL     1       0.204  -1.332  -0.329  1.00  0.00           C  
HETATM   12  O2  UNL     1       0.121  -2.430  -0.929  1.00  0.00           O  
HETATM   13  N4  UNL     1       1.478  -0.779  -0.023  1.00  0.00           N  
HETATM   14  C8  UNL     1       2.723  -1.370  -0.491  1.00  0.00           C  
HETATM   15  C9  UNL     1       3.675  -0.364  -1.046  1.00  0.00           C  
HETATM   16  C10 UNL     1       3.693   0.951  -0.349  1.00  0.00           C  
HETATM   17  C11 UNL     1       2.860   1.045   0.875  1.00  0.00           C  
HETATM   18  C12 UNL     1       1.518   0.405   0.778  1.00  0.00           C  
HETATM   19  H1  UNL     1      -1.477   1.347  -0.729  1.00  0.00           H  
HETATM   20  H2  UNL     1      -1.176  -0.653   1.180  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.224  -1.147  -1.676  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.372  -2.186  -0.251  1.00  0.00           H  
HETATM   23  H5  UNL     1      -4.054  -1.454   1.736  1.00  0.00           H  
HETATM   24  H6  UNL     1      -5.738   1.949  -0.032  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.731   1.237  -1.467  1.00  0.00           H  
HETATM   26  H8  UNL     1       3.227  -1.943   0.330  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.533  -2.129  -1.293  1.00  0.00           H  
HETATM   28  H10 UNL     1       3.538  -0.244  -2.159  1.00  0.00           H  
HETATM   29  H11 UNL     1       4.710  -0.803  -0.953  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.345   1.730  -1.088  1.00  0.00           H  
HETATM   31  H13 UNL     1       4.732   1.281  -0.079  1.00  0.00           H  
HETATM   32  H14 UNL     1       2.699   2.126   1.119  1.00  0.00           H  
HETATM   33  H15 UNL     1       3.393   0.625   1.753  1.00  0.00           H  
HETATM   34  H16 UNL     1       1.200   0.111   1.820  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   18
CONECT    3    4   19
CONECT    4    5   11   20
CONECT    5    6   21   22
CONECT    6    7    7   10
CONECT    7    8   23
CONECT    8    9    9
CONECT    9   10   24
CONECT   10   25
CONECT   11   12   12   13
CONECT   13   14   18
CONECT   14   15   26   27
CONECT   15   16   28   29
CONECT   16   17   30   31
CONECT   17   18   32   33
CONECT   18   34
END

HMDB0002053
     RDKit          3D
Histidylproline diketopiperazine
 34 36  0  0  0  0  0  0  0  0999 V2000
    0.6450    2.5501    0.2899 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4613    1.3192    0.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7680    0.8044   -0.2003 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0398   -0.5894    0.0722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2603   -1.1353   -0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4369   -0.3684   -0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2071   -0.6393    1.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1899    0.2573    1.1610 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0697    1.1008    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0114    0.7267   -0.6176 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2036   -1.3320   -0.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215   -2.4296   -0.9288 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4777   -0.7792   -0.0226 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7233   -1.3701   -0.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6751   -0.3640   -1.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6934    0.9507   -0.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8599    1.0445    0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179    0.4053    0.7785 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4770    1.3471   -0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1758   -0.6532    1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2238   -1.1466   -1.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3718   -2.1859   -0.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0540   -1.4541    1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7380    1.9488   -0.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7315    1.2371   -1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2271   -1.9431    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5325   -2.1288   -1.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5380   -0.2439   -2.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7104   -0.8028   -0.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3450    1.7305   -1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7319    1.2815   -0.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    2.1263    1.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3926    0.6247    1.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2003    0.1106    1.8202 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  2  0
  9 10  1  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 18  1  0
 18  2  1  0
 10  6  1  0
 18 13  1  0
  3 19  1  0
  4 20  1  1
  5 21  1  0
  5 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 14 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
His-pro-DKP	MeSH
Cyclo(his-pro)	MeSH
Cyclo(histidyl-prolyl)	MeSH
Histidyl-proline diketopiperazine	MeSH
Histidyl-proline diketopiperazine, (3R-cis)-isomer	MeSH
Histidyl-proline diketopiperazine, (3S-cis)-isomer	MeSH
Histidyl-proline diketopiperazine, (3S-trans)-isomer	MeSH
Histidyl-proline-diketopiperazine	MeSH

Chemical Formula

C₁₂H₁₆N₄O₂

Average Molecular Weight

248.281

Monoisotopic Molecular Weight

248.127325776

IUPAC Name

(3S,9aS)-3-(1H-imidazol-5-ylmethyl)-octahydro-1H-pyrido[1,2-a]piperazine-1,4-dione

Traditional Name

(3S,9aS)-3-(3H-imidazol-4-ylmethyl)-hexahydro-2H-pyrido[1,2-a]piperazine-1,4-dione

CAS Registry Number

53109-32-3

SMILES

[H][C@@]12CCCCN1C(=O)[C@H](CC1=CN=CN1)NC2=O

InChI Identifier

InChI=1S/C12H16N4O2/c17-11-10-3-1-2-4-16(10)12(18)9(15-11)5-8-6-13-7-14-8/h6-7,9-10H,1-5H2,(H,13,14)(H,15,17)/t9-,10-/m0/s1

InChI Key

LCXWQHWWTPOAFI-UWVGGRQHSA-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
Piperidine
Azole
Imidazole
Tertiary carboxylic acid amide
Cyclic carboximidic acid
Heteroaromatic compound
Lactam
Carboxamide group
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Azacycle
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Blood (HMDB: HMDB0002053)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 6401750)

Source

Endogenous

Endogenous (HMDB: HMDB0002053)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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
Water Solubility	9.12 g/L	ALOGPS
logP	-0.36	ALOGPS
logP	-1.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	10.95	ChemAxon
pKa (Strongest Basic)	6.74	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	64.45 m³·mol⁻¹	ChemAxon
Polarizability	24.5 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
DarkChem	[M+H]+	157.872	31661259
DarkChem	[M-H]-	156.707	31661259
DeepCCS	[M-2H]-	183.326	30932474
DeepCCS	[M+Na]+	158.285	30932474
AllCCS	[M+H]+	157.6	32859911
AllCCS	[M+H-H2O]+	153.8	32859911
AllCCS	[M+NH4]+	161.0	32859911
AllCCS	[M+Na]+	162.0	32859911
AllCCS	[M-H]-	160.2	32859911
AllCCS	[M+Na-2H]-	159.8	32859911
AllCCS	[M+HCOO]-	159.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Histidylproline diketopiperazine	[H][C@@]12CCCCN1C(=O)[C@H](CC1=CN=CN1)NC2=O	3465.1	Standard polar	33892256
Histidylproline diketopiperazine	[H][C@@]12CCCCN1C(=O)[C@H](CC1=CN=CN1)NC2=O	2620.7	Standard non polar	33892256
Histidylproline diketopiperazine	[H][C@@]12CCCCN1C(=O)[C@H](CC1=CN=CN1)NC2=O	2721.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Histidylproline diketopiperazine,1TMS,isomer #1	C[Si](C)(C)N1C=NC=C1C[C@@H]1NC(=O)[C@@H]2CCCCN2C1=O	2544.1	Semi standard non polar	33892256
Histidylproline diketopiperazine,1TMS,isomer #1	C[Si](C)(C)N1C=NC=C1C[C@@H]1NC(=O)[C@@H]2CCCCN2C1=O	2478.0	Standard non polar	33892256
Histidylproline diketopiperazine,1TMS,isomer #1	C[Si](C)(C)N1C=NC=C1C[C@@H]1NC(=O)[C@@H]2CCCCN2C1=O	4206.8	Standard polar	33892256
Histidylproline diketopiperazine,1TMS,isomer #2	C[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=C[NH]1	2307.8	Semi standard non polar	33892256
Histidylproline diketopiperazine,1TMS,isomer #2	C[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=C[NH]1	2410.2	Standard non polar	33892256
Histidylproline diketopiperazine,1TMS,isomer #2	C[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=C[NH]1	3721.4	Standard polar	33892256
Histidylproline diketopiperazine,2TMS,isomer #1	C[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=CN1[Si](C)(C)C	2384.4	Semi standard non polar	33892256
Histidylproline diketopiperazine,2TMS,isomer #1	C[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=CN1[Si](C)(C)C	2461.3	Standard non polar	33892256
Histidylproline diketopiperazine,2TMS,isomer #1	C[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=CN1[Si](C)(C)C	3511.8	Standard polar	33892256
Histidylproline diketopiperazine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=NC=C1C[C@@H]1NC(=O)[C@@H]2CCCCN2C1=O	2791.7	Semi standard non polar	33892256
Histidylproline diketopiperazine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=NC=C1C[C@@H]1NC(=O)[C@@H]2CCCCN2C1=O	2717.7	Standard non polar	33892256
Histidylproline diketopiperazine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=NC=C1C[C@@H]1NC(=O)[C@@H]2CCCCN2C1=O	4269.3	Standard polar	33892256
Histidylproline diketopiperazine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=C[NH]1	2518.1	Semi standard non polar	33892256
Histidylproline diketopiperazine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=C[NH]1	2652.7	Standard non polar	33892256
Histidylproline diketopiperazine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=C[NH]1	3752.8	Standard polar	33892256
Histidylproline diketopiperazine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=CN1[Si](C)(C)C(C)(C)C	2804.2	Semi standard non polar	33892256
Histidylproline diketopiperazine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=CN1[Si](C)(C)C(C)(C)C	2919.4	Standard non polar	33892256
Histidylproline diketopiperazine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=CN1[Si](C)(C)C(C)(C)C	3481.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Histidylproline diketopiperazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0c10-8960000000-b59521a7bf7f2dbcd98b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Histidylproline diketopiperazine 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 - Histidylproline diketopiperazine 10V, Positive-QTOF	splash10-0002-0090000000-843d3723786addf5c81b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 20V, Positive-QTOF	splash10-006t-0090000000-38a066bbd349061998cc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 40V, Positive-QTOF	splash10-001i-9100000000-98e8fd70b7c52af6ad80	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 10V, Negative-QTOF	splash10-0002-0190000000-1981c342d35a74baaaf5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 20V, Negative-QTOF	splash10-001j-8940000000-df121bc941f701b83e43	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 40V, Negative-QTOF	splash10-001i-9400000000-bb22aeb05ef45a82e903	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 10V, Positive-QTOF	splash10-0002-0090000000-2d6df444943bd8abf9e0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 20V, Positive-QTOF	splash10-0002-0090000000-7a61131b9929146e0cc3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 40V, Positive-QTOF	splash10-000t-9560000000-d98006bfa210732b955f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 10V, Negative-QTOF	splash10-0002-0090000000-9825da4495af4eed0ee2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 20V, Negative-QTOF	splash10-0002-1290000000-03e21d76de28525b9ad9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 40V, Negative-QTOF	splash10-0006-9410000000-f6ed33b9456dfc589d83	2021-09-24	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

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000022 (0.000011-0.000033) uM	Adult (>18 years old)	Both	Normal	6401750	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

FDB022818

KNApSAcK ID

Not Available

Chemspider ID

58646

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65137

PDB ID

Not Available

ChEBI ID

90039

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Ma, Yaping; Bai, Wei; Zhong, Fei; Cui, Xueyun. Method for the preparation of all stereoisomers of cyclo(histidylproline). Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 11pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Leduque P, Jackson IM, Kervran A, Aratan-Spire S, Czernichow P, Dubois PM: Histidyl-proline diketopiperazine (His-Pro DKP) immunoreactivity is present in the glucagon-containing cells of the human fetal pancreas. J Clin Invest. 1987 Mar;79(3):875-80. [PubMed:3102558 ]
Takahara Y, Battaini F, Ross DD, Akman SA, Bachur NR, Bailey KR, Lakatos E, Peterkofsky A: Detection in human serum by radioimmunoassay of histidyl-proline diketopiperazine, a metabolite of thyrotropin-releasing hormone. J Clin Endocrinol Metab. 1983 Feb;56(2):312-9. [PubMed:6401750 ]

Showing metabocard for Histidylproline diketopiperazine (HMDB0002053)

MOL for HMDB0002053 (Histidylproline diketopiperazine)

3D MOL for HMDB0002053 (Histidylproline diketopiperazine)

3D SDF for HMDB0002053 (Histidylproline diketopiperazine)

3D-SDF for HMDB0002053 (Histidylproline diketopiperazine)

PDB for HMDB0002053 (Histidylproline diketopiperazine)

3D PDB for HMDB0002053 (Histidylproline diketopiperazine)

SMILES for HMDB0002053 (Histidylproline diketopiperazine)

INCHI for HMDB0002053 (Histidylproline diketopiperazine)

Structure for HMDB0002053 (Histidylproline diketopiperazine)

3D Structure for HMDB0002053 (Histidylproline diketopiperazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra