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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2017-08-01 02:16:03 UTC

Update Date

2022-03-07 03:18:00 UTC

HMDB ID

HMDB0094673

Secondary Accession Numbers

HMDB94673

Metabolite Identification

Common Name

Cyclo(Leu-Phe)

Description

Cyclo(leu-phe), also known as cyclo(Phe-leu) or cFL, is classified as an alpha amino acid or an Alpha amino acid derivative. Alpha amino acids 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(leu-phe) is considered to be a practically insoluble (in water) and a moderately acidic compound. Cyclo(leu-phe) can be found in feces.

Structure

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

HMDB0094673
     RDKit          3D
Cyclo(Leu-Phe)
 39 40  0  0  0  0  0  0  0  0999 V2000
    4.9250    1.1256    0.9875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590    0.0661    0.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5464   -0.9732   -0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7639    0.7789   -0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5988   -0.0283   -0.4752 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6753    0.9115   -1.1517 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5589    0.5188   -1.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4218    1.3929   -2.0268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8808   -0.8447   -0.9577 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2527   -1.3358   -1.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3522   -0.6215   -0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6721   -0.8836    0.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7141   -0.2656    1.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4582    0.6528    0.6994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1586    0.9274   -0.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0956    0.2876   -1.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4306   -0.9800    0.4222 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7859   -0.5807    0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3001   -0.6657    1.9229 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4005    0.9301    1.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4647    2.1402    1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6580    1.1558    0.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5447   -0.3244    1.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0826   -1.1210   -1.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6228   -0.7614   -0.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5309   -1.9398    0.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4196    1.6028    0.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1760    1.2803   -0.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8815   -0.8540   -1.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5619    2.3583   -1.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1967   -1.5189   -1.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3846   -1.4332   -2.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -2.4198   -0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0763   -1.6117    1.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9886   -0.4483    2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3021    1.1709    1.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7341    1.6503   -1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9171    0.5398   -2.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1910    0.1216    2.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  2  0
 18 19  1  0
 18  5  1  0
 16 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  8 30  1  0
  9 31  1  6
 10 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 19 39  1  0
M  END

  Mrv1652308011704162D          

 21 22  0  0  1  0            999 V2000
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  8  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  6  0  0  0
 13  9  1  6  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 12  1  0  0  0  0
 16 15  2  0  0  0  0
 17 13  1  0  0  0  0
 17 14  2  0  0  0  0
 18 14  1  0  0  0  0
 19 15  1  0  0  0  0
 12 20  1  1  0  0  0
 13 21  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0094673

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC(C)C)N=C(O)[C@]([H])(CC2=CC=CC=C2)N=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20N2O2/c1-10(2)8-12-14(18)17-13(15(19)16-12)9-11-6-4-3-5-7-11/h3-7,10,12-13H,8-9H2,1-2H3,(H,16,19)(H,17,18)/t12-,13-/m0/s1

> <INCHI_KEY>
QPDMOMIYLJMOQJ-STQMWFEESA-N

> <FORMULA>
C15H20N2O2

> <MOLECULAR_WEIGHT>
260.337

> <EXACT_MASS>
260.152477892

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.752514724745907

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,6S)-3-benzyl-6-(2-methylpropyl)-3,6-dihydropyrazine-2,5-diol

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
1.7634345969843928

> <ALOGPS_LOGS>
-3.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
5.663816404865584

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.708674206845382

> <JCHEM_PKA_STRONGEST_BASIC>
4.680273478213693

> <JCHEM_POLAR_SURFACE_AREA>
65.18

> <JCHEM_REFRACTIVITY>
73.93080000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S)-3-benzyl-6-(2-methylpropyl)-3,6-dihydropyrazine-2,5-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0094673
     RDKit          3D
Cyclo(Leu-Phe)
 39 40  0  0  0  0  0  0  0  0999 V2000
    4.9250    1.1256    0.9875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590    0.0661    0.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5464   -0.9732   -0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7639    0.7789   -0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5988   -0.0283   -0.4752 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6753    0.9115   -1.1517 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5589    0.5188   -1.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4218    1.3929   -2.0268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8808   -0.8447   -0.9577 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2527   -1.3358   -1.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3522   -0.6215   -0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6721   -0.8836    0.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7141   -0.2656    1.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4582    0.6528    0.6994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1586    0.9274   -0.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0956    0.2876   -1.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4306   -0.9800    0.4222 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7859   -0.5807    0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3001   -0.6657    1.9229 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4005    0.9301    1.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4647    2.1402    1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6580    1.1558    0.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5447   -0.3244    1.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0826   -1.1210   -1.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6228   -0.7614   -0.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5309   -1.9398    0.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4196    1.6028    0.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1760    1.2803   -0.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8815   -0.8540   -1.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5619    2.3583   -1.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1967   -1.5189   -1.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3846   -1.4332   -2.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -2.4198   -0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0763   -1.6117    1.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9886   -0.4483    2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3021    1.1709    1.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7341    1.6503   -1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9171    0.5398   -2.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1910    0.1216    2.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  2  0
 18 19  1  0
 18  5  1  0
 16 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  8 30  1  0
  9 31  1  6
 10 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 19 39  1  0
M  END

HEADER    PROTEIN                                 01-AUG-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-AUG-17         0                                  
HETATM    1  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       4.001   6.930   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       4.001   3.850   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0       1.334   5.390   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       5.335   3.080   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   11                                                       
CONECT    7    5   11                                                       
CONECT    8   10   12                                                       
CONECT    9   11   13                                                       
CONECT   10    1    2    8                                                  
CONECT   11    6    7    9                                                  
CONECT   12    8   14   16   20                                             
CONECT   13    9   15   17   21                                             
CONECT   14   12   17   18                                                  
CONECT   15   13   16   19                                                  
CONECT   16   12   15                                                       
CONECT   17   13   14                                                       
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0094673
HETATM    1  C1  UNL     1       4.925   1.126   0.988  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.859   0.066   0.661  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.546  -0.973  -0.189  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.764   0.779  -0.042  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.599  -0.028  -0.475  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.675   0.911  -1.152  1.00  0.00           N  
HETATM    7  C6  UNL     1      -0.559   0.519  -1.397  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.422   1.393  -2.027  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.881  -0.845  -0.958  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.253  -1.336  -1.173  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.352  -0.622  -0.547  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.672  -0.884   0.775  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.714  -0.266   1.422  1.00  0.00           C  
HETATM   14  C12 UNL     1      -5.458   0.653   0.699  1.00  0.00           C  
HETATM   15  C13 UNL     1      -5.159   0.927  -0.613  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.096   0.288  -1.251  1.00  0.00           C  
HETATM   17  N2  UNL     1      -0.431  -0.980   0.422  1.00  0.00           N  
HETATM   18  C15 UNL     1       0.786  -0.581   0.664  1.00  0.00           C  
HETATM   19  O2  UNL     1       1.300  -0.666   1.923  1.00  0.00           O  
HETATM   20  H1  UNL     1       5.401   0.930   1.957  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.465   2.140   1.017  1.00  0.00           H  
HETATM   22  H3  UNL     1       5.658   1.156   0.149  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.545  -0.324   1.628  1.00  0.00           H  
HETATM   24  H5  UNL     1       4.083  -1.121  -1.167  1.00  0.00           H  
HETATM   25  H6  UNL     1       5.623  -0.761  -0.355  1.00  0.00           H  
HETATM   26  H7  UNL     1       4.531  -1.940   0.393  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.420   1.603   0.646  1.00  0.00           H  
HETATM   28  H9  UNL     1       3.176   1.280  -0.961  1.00  0.00           H  
HETATM   29  H10 UNL     1       1.881  -0.854  -1.130  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.562   2.358  -1.725  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.197  -1.519  -1.552  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.385  -1.433  -2.297  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.270  -2.420  -0.843  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.076  -1.612   1.336  1.00  0.00           H  
HETATM   35  H16 UNL     1      -4.989  -0.448   2.452  1.00  0.00           H  
HETATM   36  H17 UNL     1      -6.302   1.171   1.181  1.00  0.00           H  
HETATM   37  H18 UNL     1      -5.734   1.650  -1.203  1.00  0.00           H  
HETATM   38  H19 UNL     1      -3.917   0.540  -2.311  1.00  0.00           H  
HETATM   39  H20 UNL     1       1.191   0.122   2.551  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4   23
CONECT    3   24   25   26
CONECT    4    5   27   28
CONECT    5    6   18   29
CONECT    6    7    7
CONECT    7    8    9
CONECT    8   30
CONECT    9   10   17   31
CONECT   10   11   32   33
CONECT   11   12   12   16
CONECT   12   13   34
CONECT   13   14   14   35
CONECT   14   15   36
CONECT   15   16   16   37
CONECT   16   38
CONECT   17   18   18
CONECT   18   19
CONECT   19   39
END

HMDB0094673
     RDKit          3D
Cyclo(Leu-Phe)
 39 40  0  0  0  0  0  0  0  0999 V2000
    4.9250    1.1256    0.9875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590    0.0661    0.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5464   -0.9732   -0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7639    0.7789   -0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5988   -0.0283   -0.4752 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6753    0.9115   -1.1517 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5589    0.5188   -1.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4218    1.3929   -2.0268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8808   -0.8447   -0.9577 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2527   -1.3358   -1.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3522   -0.6215   -0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6721   -0.8836    0.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7141   -0.2656    1.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4582    0.6528    0.6994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1586    0.9274   -0.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0956    0.2876   -1.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4306   -0.9800    0.4222 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7859   -0.5807    0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3001   -0.6657    1.9229 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4005    0.9301    1.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4647    2.1402    1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6580    1.1558    0.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5447   -0.3244    1.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0826   -1.1210   -1.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6228   -0.7614   -0.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5309   -1.9398    0.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4196    1.6028    0.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1760    1.2803   -0.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8815   -0.8540   -1.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5619    2.3583   -1.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1967   -1.5189   -1.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3846   -1.4332   -2.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -2.4198   -0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0763   -1.6117    1.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9886   -0.4483    2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3021    1.1709    1.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7341    1.6503   -1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9171    0.5398   -2.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1910    0.1216    2.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  2  0
 18 19  1  0
 18  5  1  0
 16 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  8 30  1  0
  9 31  1  6
 10 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3S,6S)-3-(2-Methylpropyl)-6-(phenylmethyl)-2,5-piperazinedione	ChEBI
cFL	ChEBI
Cyclo(L-leu-L-phe)	ChEBI
Cyclo(L-leucyl-L-phenylalanyl)	ChEBI
Cyclo(L-phe-L-leu)	ChEBI
Cyclo(phe-leu)	ChEBI
L-Phenylalanyl-L-leucine diketopiperazine	ChEBI
(3S,6S)-3-Benzyl-6-(2-methylpropyl)piperazine-2,5-dione	Kegg
Cyclo(leucyl-phenylalanyl)	HMDB
cyclo(Leu-phe)	ChEBI

Chemical Formula

C₁₅H₂₀N₂O₂

Average Molecular Weight

260.337

Monoisotopic Molecular Weight

260.152477892

IUPAC Name

(3S,6S)-3-benzyl-6-(2-methylpropyl)-3,6-dihydropyrazine-2,5-diol

Traditional Name

(3S,6S)-3-benzyl-6-(2-methylpropyl)-3,6-dihydropyrazine-2,5-diol

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC(C)C)N=C(O)[C@]([H])(CC2=CC=CC=C2)N=C1O

InChI Identifier

InChI=1S/C15H20N2O2/c1-10(2)8-12-14(18)17-13(15(19)16-12)9-11-6-4-3-5-7-11/h3-7,10,12-13H,8-9H2,1-2H3,(H,16,19)(H,17,18)/t12-,13-/m0/s1

InChI Key

QPDMOMIYLJMOQJ-STQMWFEESA-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
Monocyclic benzene moiety
1,4-diazinane
Piperazine
Benzenoid
Secondary carboxylic acid amide
Lactam
Carboxamide group
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

2,5-diketopiperazines (CHEBI:71608 )

Ontology

Not Available

Feces (PMID: 27275383)

Source

Exogenous

Exogenous (HMDB: HMDB0094673)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.36	ALOGPS
logP	1.76	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	2.71	ChemAxon
pKa (Strongest Basic)	4.68	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.18 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.93 m³·mol⁻¹	ChemAxon
Polarizability	28.75 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
DarkChem	[M+H]+	162.918	31661259
DarkChem	[M-H]-	162.366	31661259
DeepCCS	[M+H]+	159.383	30932474
DeepCCS	[M-H]-	157.025	30932474
DeepCCS	[M-2H]-	190.87	30932474
DeepCCS	[M+Na]+	166.003	30932474
AllCCS	[M+H]+	163.2	32859911
AllCCS	[M+H-H2O]+	159.6	32859911
AllCCS	[M+NH4]+	166.5	32859911
AllCCS	[M+Na]+	167.5	32859911
AllCCS	[M-H]-	166.1	32859911
AllCCS	[M+Na-2H]-	166.3	32859911
AllCCS	[M+HCOO]-	166.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyclo(Leu-Phe)	[H][C@@]1(CC(C)C)N=C(O)[C@]([H])(CC2=CC=CC=C2)N=C1O	2963.9	Standard polar	33892256
Cyclo(Leu-Phe)	[H][C@@]1(CC(C)C)N=C(O)[C@]([H])(CC2=CC=CC=C2)N=C1O	2099.2	Standard non polar	33892256
Cyclo(Leu-Phe)	[H][C@@]1(CC(C)C)N=C(O)[C@]([H])(CC2=CC=CC=C2)N=C1O	2084.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cyclo(Leu-Phe),1TMS,isomer #1	CC(C)C[C@@H]1N=C(O[Si](C)(C)C)[C@H](CC2=CC=CC=C2)N=C1O	2052.9	Semi standard non polar	33892256
Cyclo(Leu-Phe),1TMS,isomer #2	CC(C)C[C@@H]1N=C(O)[C@H](CC2=CC=CC=C2)N=C1O[Si](C)(C)C	2076.8	Semi standard non polar	33892256
Cyclo(Leu-Phe),2TMS,isomer #1	CC(C)C[C@@H]1N=C(O[Si](C)(C)C)[C@H](CC2=CC=CC=C2)N=C1O[Si](C)(C)C	2129.9	Semi standard non polar	33892256
Cyclo(Leu-Phe),1TBDMS,isomer #1	CC(C)C[C@@H]1N=C(O[Si](C)(C)C(C)(C)C)[C@H](CC2=CC=CC=C2)N=C1O	2255.1	Semi standard non polar	33892256
Cyclo(Leu-Phe),1TBDMS,isomer #2	CC(C)C[C@@H]1N=C(O)[C@H](CC2=CC=CC=C2)N=C1O[Si](C)(C)C(C)(C)C	2264.8	Semi standard non polar	33892256
Cyclo(Leu-Phe),2TBDMS,isomer #1	CC(C)C[C@@H]1N=C(O[Si](C)(C)C(C)(C)C)[C@H](CC2=CC=CC=C2)N=C1O[Si](C)(C)C(C)(C)C	2517.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclo(Leu-Phe) GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9640000000-609ba4c52300440a234d	2017-09-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclo(Leu-Phe) GC-MS (2 TMS) - 70eV, Positive	splash10-000f-9327000000-bec89ae75ba379a7ea85	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclo(Leu-Phe) 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(Leu-Phe) 10V, Negative-QTOF	splash10-0aor-0090000000-b6e391a32751e9526552	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclo(Leu-Phe) 20V, Negative-QTOF	splash10-00l6-9410000000-9679f2e8b6ca50c8a1aa	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclo(Leu-Phe) 40V, Negative-QTOF	splash10-0frx-9400000000-0f2097d0e4a2f274f4f4	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclo(Leu-Phe) 10V, Positive-QTOF	splash10-03di-0090000000-174424947d50accea585	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclo(Leu-Phe) 20V, Positive-QTOF	splash10-03dl-4390000000-77c611261efe12aab520	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclo(Leu-Phe) 40V, Positive-QTOF	splash10-052f-9200000000-c5231f4b533d04fab5af	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclo(Leu-Phe) 10V, Positive-QTOF	splash10-03di-0090000000-a8510df7876ad10d1e91	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclo(Leu-Phe) 20V, Positive-QTOF	splash10-03xu-1390000000-16ca9b59a6f7b443444b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclo(Leu-Phe) 40V, Positive-QTOF	splash10-0006-9410000000-c35891b7cf45708017dc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclo(Leu-Phe) 10V, Negative-QTOF	splash10-0a4i-0090000000-a7fd50b20d0fcccddc5f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclo(Leu-Phe) 20V, Negative-QTOF	splash10-052f-5390000000-c81968f90f3566dfcd8f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclo(Leu-Phe) 40V, Negative-QTOF	splash10-0006-9310000000-e50ec5c1775767a23bef	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

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

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5429202

KEGG Compound ID

C20519

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7076347

PDB ID

Not Available

ChEBI ID

71608

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Cyclo(Leu-Phe) (HMDB0094673)

MOL for HMDB0094673 (Cyclo(Leu-Phe))

3D MOL for HMDB0094673 (Cyclo(Leu-Phe))

3D SDF for HMDB0094673 (Cyclo(Leu-Phe))

3D-SDF for HMDB0094673 (Cyclo(Leu-Phe))

PDB for HMDB0094673 (Cyclo(Leu-Phe))

3D PDB for HMDB0094673 (Cyclo(Leu-Phe))

SMILES for HMDB0094673 (Cyclo(Leu-Phe))

INCHI for HMDB0094673 (Cyclo(Leu-Phe))

Structure for HMDB0094673 (Cyclo(Leu-Phe))

3D Structure for HMDB0094673 (Cyclo(Leu-Phe))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra