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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 19:04:50 UTC

Update Date

2022-03-07 02:54:02 UTC

HMDB ID

HMDB0034276

Secondary Accession Numbers

HMDB34276

Metabolite Identification

Common Name

L,L-Cyclo(leucylprolyl)

Description

L,L-Cyclo(leucylprolyl), also known as cyclo(leu-pro) or cyclo(L-prolyl-L-leucyl), 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. L,L-Cyclo(leucylprolyl) is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on L,L-Cyclo(leucylprolyl).

Structure

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

HMDB0034276
     RDKit          3D
L,L-Cyclo(leucylprolyl)
 33 34  0  0  0  0  0  0  0  0999 V2000
    3.4844    0.5830    0.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9192   -0.5657   -0.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9702   -0.9404   -1.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6683   -0.2232   -1.1257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5564    0.2246   -0.2030 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1914   -0.7868    0.7610 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0582   -0.6942    1.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3657   -1.4796    2.3395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0231    0.3549    1.0292 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4566   -0.0307    1.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1822    0.7309    0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3005    0.3944   -0.9858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9597    0.4379   -0.4344 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561    0.5398   -1.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438    0.9060   -2.2033 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8201    1.4106   -0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8041    0.9401    1.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4052    0.2164    0.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7920   -1.4178    0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5354   -1.6005   -2.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8810   -1.3735   -0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3049    0.0019   -1.9227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8452    0.6053   -1.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3062   -1.1419   -1.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8510    1.1561    0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8519   -1.5682    0.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    1.3367    1.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8285    0.3864    2.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6646   -1.0956    1.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2139    0.3989    0.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1211    1.8300    0.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4276    1.1125   -1.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5641   -0.6486   -1.2895 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  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14  5  1  0
 13  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  1
  6 26  1  0
  9 27  1  1
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
M  END


  Mrv1652310161901032D          

 17 18  0  0  1  0            999 V2000
    6.1368    1.2375    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
    1.2949    0.4125    0.0000 C   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
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 N   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
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4782   -0.8205    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  6  0  0  0
  9  4  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  2  0  0  0  0
 13  5  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  2  0  0  0  0
  8 16  1  1  0  0  0
  9 17  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0034276

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CCCN1C(=O)[C@]([H])(CC(C)C)N=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C11H18N2O2/c1-7(2)6-8-11(15)13-5-3-4-9(13)10(14)12-8/h7-9H,3-6H2,1-2H3,(H,12,14)/t8-,9-/m0/s1

> <INCHI_KEY>
SZJNCZMRZAUNQT-IUCAKERBSA-N

> <FORMULA>
C11H18N2O2

> <MOLECULAR_WEIGHT>
210.277

> <EXACT_MASS>
210.136827828

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
22.853689858113718

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,8aS)-1-hydroxy-3-(2-methylpropyl)-3H,4H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one

> <ALOGPS_LOGP>
0.61

> <JCHEM_LOGP>
1.2733418663333338

> <ALOGPS_LOGS>
-1.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.38589310770847

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.7952179664798855

> <JCHEM_PKA_STRONGEST_BASIC>
1.5655394307774737

> <JCHEM_POLAR_SURFACE_AREA>
52.9

> <JCHEM_REFRACTIVITY>
56.479200000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.28e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,8aS)-1-hydroxy-3-(2-methylpropyl)-3H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034276
     RDKit          3D
L,L-Cyclo(leucylprolyl)
 33 34  0  0  0  0  0  0  0  0999 V2000
    3.4844    0.5830    0.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9192   -0.5657   -0.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9702   -0.9404   -1.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6683   -0.2232   -1.1257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5564    0.2246   -0.2030 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1914   -0.7868    0.7610 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0582   -0.6942    1.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3657   -1.4796    2.3395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0231    0.3549    1.0292 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4566   -0.0307    1.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1822    0.7309    0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3005    0.3944   -0.9858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9597    0.4379   -0.4344 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561    0.5398   -1.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438    0.9060   -2.2033 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8201    1.4106   -0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8041    0.9401    1.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4052    0.2164    0.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7920   -1.4178    0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5354   -1.6005   -2.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8810   -1.3735   -0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3049    0.0019   -1.9227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8452    0.6053   -1.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3062   -1.1419   -1.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8510    1.1561    0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8519   -1.5682    0.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    1.3367    1.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8285    0.3864    2.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6646   -1.0956    1.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2139    0.3989    0.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1211    1.8300    0.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4276    1.1125   -1.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5641   -0.6486   -1.2895 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  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14  5  1  0
 13  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  1
  6 26  1  0
  9 27  1  1
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
M  END

HEADER    PROTEIN                                 16-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-OCT-19         0                                  
HETATM    1  C   UNK     0      11.455   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.122  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.122   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       7.454   0.000   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       4.787   1.540   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM   16  H   UNK     0       7.454   3.080   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       4.626  -1.532   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    4    5                                                       
CONECT    4    3    9                                                       
CONECT    5    3   13                                                       
CONECT    6    7    8                                                       
CONECT    7    1    2    6                                                  
CONECT    8    6   11   12   16                                             
CONECT    9    4   10   13   17                                             
CONECT   10    9   12   14                                                  
CONECT   11    8   13   15                                                  
CONECT   12    8   10                                                       
CONECT   13    5    9   11                                                  
CONECT   14   10                                                            
CONECT   15   11                                                            
CONECT   16    8                                                            
CONECT   17    9                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0034276
HETATM    1  C1  UNL     1       3.484   0.583   0.396  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.919  -0.566  -0.393  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.970  -0.940  -1.438  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.668  -0.223  -1.126  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.556   0.225  -0.203  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.191  -0.787   0.761  1.00  0.00           N  
HETATM    7  C6  UNL     1      -1.058  -0.694   1.425  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.366  -1.480   2.340  1.00  0.00           O  
HETATM    9  C7  UNL     1      -2.023   0.355   1.029  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.457  -0.031   1.318  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.182   0.731   0.199  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.300   0.394  -0.986  1.00  0.00           C  
HETATM   13  N2  UNL     1      -1.960   0.438  -0.434  1.00  0.00           N  
HETATM   14  C11 UNL     1      -0.656   0.540  -1.000  1.00  0.00           C  
HETATM   15  O2  UNL     1      -0.544   0.906  -2.203  1.00  0.00           O  
HETATM   16  H1  UNL     1       3.820   1.411  -0.273  1.00  0.00           H  
HETATM   17  H2  UNL     1       2.804   0.940   1.190  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.405   0.216   0.901  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.792  -1.418   0.278  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.535  -1.601  -2.204  1.00  0.00           H  
HETATM   21  H6  UNL     1       4.881  -1.373  -0.957  1.00  0.00           H  
HETATM   22  H7  UNL     1       4.305   0.002  -1.923  1.00  0.00           H  
HETATM   23  H8  UNL     1       1.845   0.605  -1.836  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.306  -1.142  -1.633  1.00  0.00           H  
HETATM   25  H10 UNL     1       0.851   1.156   0.344  1.00  0.00           H  
HETATM   26  H11 UNL     1       0.852  -1.568   0.953  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.821   1.337   1.474  1.00  0.00           H  
HETATM   28  H13 UNL     1      -3.828   0.386   2.266  1.00  0.00           H  
HETATM   29  H14 UNL     1      -3.665  -1.096   1.170  1.00  0.00           H  
HETATM   30  H15 UNL     1      -5.214   0.399   0.077  1.00  0.00           H  
HETATM   31  H16 UNL     1      -4.121   1.830   0.411  1.00  0.00           H  
HETATM   32  H17 UNL     1      -3.428   1.113  -1.823  1.00  0.00           H  
HETATM   33  H18 UNL     1      -3.564  -0.649  -1.290  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    4   19
CONECT    3   20   21   22
CONECT    4    5   23   24
CONECT    5    6   14   25
CONECT    6    7   26
CONECT    7    8    8    9
CONECT    9   10   13   27
CONECT   10   11   28   29
CONECT   11   12   30   31
CONECT   12   13   32   33
CONECT   13   14
CONECT   14   15   15
END

HMDB0034276
     RDKit          3D
L,L-Cyclo(leucylprolyl)
 33 34  0  0  0  0  0  0  0  0999 V2000
    3.4844    0.5830    0.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9192   -0.5657   -0.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9702   -0.9404   -1.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6683   -0.2232   -1.1257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5564    0.2246   -0.2030 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1914   -0.7868    0.7610 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0582   -0.6942    1.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3657   -1.4796    2.3395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0231    0.3549    1.0292 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4566   -0.0307    1.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1822    0.7309    0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3005    0.3944   -0.9858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9597    0.4379   -0.4344 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561    0.5398   -1.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438    0.9060   -2.2033 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8201    1.4106   -0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8041    0.9401    1.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4052    0.2164    0.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7920   -1.4178    0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5354   -1.6005   -2.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8810   -1.3735   -0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3049    0.0019   -1.9227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8452    0.6053   -1.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3062   -1.1419   -1.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8510    1.1561    0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8519   -1.5682    0.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    1.3367    1.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8285    0.3864    2.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6646   -1.0956    1.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2139    0.3989    0.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1211    1.8300    0.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4276    1.1125   -1.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5641   -0.6486   -1.2895 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  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14  5  1  0
 13  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  1
  6 26  1  0
  9 27  1  1
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Cyclo(L-leucyl-L-prolyl)	ChEBI
Cyclo(L-pro-L-leu)	ChEBI
Cyclo(L-prolyl-L-leucyl)	ChEBI
Cyclo(leu-pro)	ChEBI
Cyclo(pro-leu)	ChEBI
Cyclo-L-leu-L-pro	ChEBI
Gancidin W	ChEBI
L-Cyclo(leu-pro)	ChEBI
L-Cyclo(leucyloprolyl)	ChEBI
L-Leucyl-L-proline lactam	ChEBI
Cyclo(S-leucyl-S-prolyl)	HMDB
Cyclo(leucyl-prolyl)	HMDB
Cyclo(L-leu-L-pro)	HMDB
Cyclo(proline-leucine)	HMDB
Cyclo-L-prolyl-L-leucine	HMDB
L-Leucyl-L-prolyl lactam	HMDB
Maculosin 6	HMDB
cis-Cyclo(L-leu-L-pro)	HMDB
L,L-cyclo(Leucylprolyl)	ChEBI
L,L-Cyclo(leucylprolyl)	HMDB

Chemical Formula

C₁₁H₁₈N₂O₂

Average Molecular Weight

210.277

Monoisotopic Molecular Weight

210.136827828

IUPAC Name

(3S,8aS)-1-hydroxy-3-(2-methylpropyl)-3H,4H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one

Traditional Name

(3S,8aS)-1-hydroxy-3-(2-methylpropyl)-3H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one

CAS Registry Number

2873-36-1

SMILES

[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)NC2=O

InChI Identifier

InChI=1S/C11H18N2O2/c1-7(2)6-8-11(15)13-5-3-4-9(13)10(14)12-8/h7-9H,3-6H2,1-2H3,(H,12,14)/t8-,9-/m0/s1

InChI Key

SZJNCZMRZAUNQT-IUCAKERBSA-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
Pyrrolidine
Tertiary carboxylic acid amide
Secondary carboxylic acid amide
Lactam
Carboxamide group
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 24740205)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Extracellular (HMDB: HMDB0034276)
Cytoplasm (HMDB: HMDB0034276)

Source

Exogenous

Exogenous (HMDB: HMDB0034276)

Food

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	168 - 172 °C	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	44.6 g/L	ALOGPS
logP	0.61	ALOGPS
logP	1.27	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	4.8	ChemAxon
pKa (Strongest Basic)	1.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	56.48 m³·mol⁻¹	ChemAxon
Polarizability	22.85 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	182.178	30932474
DeepCCS	[M+Na]+	156.991	30932474
AllCCS	[M+H]+	148.4	32859911
AllCCS	[M+H-H2O]+	144.6	32859911
AllCCS	[M+NH4]+	152.0	32859911
AllCCS	[M+Na]+	153.0	32859911
AllCCS	[M-H]-	151.1	32859911
AllCCS	[M+Na-2H]-	151.5	32859911
AllCCS	[M+HCOO]-	152.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	3.1 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0148 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.66 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	37.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1770.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	275.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	139.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	99.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	375.2 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	456.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	95.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	844.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	349.4 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	1208.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	233.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	311.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	293.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	253.5 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	29.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L,L-Cyclo(leucylprolyl)	[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)NC2=O	2808.8	Standard polar	33892256
L,L-Cyclo(leucylprolyl)	[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)NC2=O	1618.6	Standard non polar	33892256
L,L-Cyclo(leucylprolyl)	[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)NC2=O	1958.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L,L-Cyclo(leucylprolyl),1TMS,isomer #1	CC(C)C[C@H]1C(=O)N2CCC[C@H]2C(=O)N1[Si](C)(C)C	1800.3	Semi standard non polar	33892256
L,L-Cyclo(leucylprolyl),1TMS,isomer #1	CC(C)C[C@H]1C(=O)N2CCC[C@H]2C(=O)N1[Si](C)(C)C	1850.9	Standard non polar	33892256
L,L-Cyclo(leucylprolyl),1TBDMS,isomer #1	CC(C)C[C@H]1C(=O)N2CCC[C@H]2C(=O)N1[Si](C)(C)C(C)(C)C	2021.1	Semi standard non polar	33892256
L,L-Cyclo(leucylprolyl),1TBDMS,isomer #1	CC(C)C[C@H]1C(=O)N2CCC[C@H]2C(=O)N1[Si](C)(C)C(C)(C)C	2120.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - L,L-Cyclo(leucylprolyl) 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) , positive-QTOF	splash10-03k9-7970000000-995c2fe3f83730e940dc	2019-05-16	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) , positive-QTOF	splash10-03k9-4950000000-327189e6a49090508fca	2019-05-16	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) , positive-QTOF	splash10-0fwl-0920000000-e1dc27828630ca176f2c	2019-05-16	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 35V, Positive-QTOF	splash10-00di-9410000000-0cf0537e03d60ce59354	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 10V, Positive-QTOF	splash10-03di-0090000000-eb9001f792e6e5419860	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 20V, Positive-QTOF	splash10-03di-3290000000-68aae20dc8ea6289a74a	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 40V, Positive-QTOF	splash10-0603-9000000000-f92521c806732fe0bf3e	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 10V, Negative-QTOF	splash10-0a4i-0190000000-04de6efd098f4d8b9c2b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 20V, Negative-QTOF	splash10-0aou-9210000000-d251726d15faaf148927	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 40V, Negative-QTOF	splash10-1000-9100000000-213ecebbd718c39905c3	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 10V, Positive-QTOF	splash10-03di-0090000000-d21d6775448881318bd6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 20V, Positive-QTOF	splash10-03di-8390000000-83409e46a4b2e1d76db3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 40V, Positive-QTOF	splash10-00di-9000000000-d422c9c1874a73235661	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 10V, Negative-QTOF	splash10-0a4i-0090000000-b31e4b4ae49103bba07c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 20V, Negative-QTOF	splash10-0a4i-0090000000-98eb3f95fa203c20ca6a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 40V, Negative-QTOF	splash10-0006-9100000000-7eafcc22317d1159e734	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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	Adult (>18 years old)	Both	Normal	24740205	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25762808	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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

FDB093682

KNApSAcK ID

C00018662

Chemspider ID

5428292

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7074739

PDB ID

Not Available

ChEBI ID

133094

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for L,L-Cyclo(leucylprolyl) (HMDB0034276)

MOL for HMDB0034276 (L,L-Cyclo(leucylprolyl))

3D MOL for HMDB0034276 (L,L-Cyclo(leucylprolyl))

3D SDF for HMDB0034276 (L,L-Cyclo(leucylprolyl))

3D-SDF for HMDB0034276 (L,L-Cyclo(leucylprolyl))

PDB for HMDB0034276 (L,L-Cyclo(leucylprolyl))

3D PDB for HMDB0034276 (L,L-Cyclo(leucylprolyl))

SMILES for HMDB0034276 (L,L-Cyclo(leucylprolyl))

INCHI for HMDB0034276 (L,L-Cyclo(leucylprolyl))

Structure for HMDB0034276 (L,L-Cyclo(leucylprolyl))

3D Structure for HMDB0034276 (L,L-Cyclo(leucylprolyl))

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra