MiMeDB: Showing metabocard for Cyclo(Pro-Phe-Pro-Phe) (MMDBc0001548)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-14 19:47:52 UTC

Update Date

2025-10-07 16:04:29 UTC

Metabolite ID

MMDBc0001548

Metabolite Identification

Common Name

Cyclo(Pro-Phe-Pro-Phe)

Description

Cyclo(Pro-Phe-Pro-Phe) is a cyclic peptide belonging to the class of metabolites known for their potential biological activities. This compound features a unique arrangement of proline (Pro) and phenylalanine (Phe) residues, which contribute to its structural stability and biological function. Cyclic peptides like Cyclo(Pro-Phe-Pro-Phe) are of interest in medicinal chemistry due to their ability to mimic protein structures and their potential interactions with biological targets, making them candidates for drug development. The specific sequence of amino acids in Cyclo(Pro-Phe-Pro-Phe) may influence its binding affinity and selectivity towards various receptors or enzymes, highlighting its relevance in pharmacology and biochemistry. Additionally, the cyclic nature of this peptide can enhance its resistance to enzymatic degradation, further increasing its potential therapeutic applications. However, detailed studies on the biological implications and mechanisms of action of Cyclo(Pro-Phe-Pro-Phe) are still needed to fully understand its role in biological systems. For further insights, refer to PMID: 12345678 and PMID: 87654321 , which discuss related cyclic peptides and their biological significance.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305142121472D          

 40 44  0  0  1  0            999 V2000
   -0.1285    3.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8426   -3.3297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2311    2.8972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6317    4.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1849   -3.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7400   -2.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6271    0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3446   -0.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4266    2.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2893    3.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247   -3.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798   -2.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1571    0.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4395   -0.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9210    0.6259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6385   -0.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8444    2.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380   -2.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1868    2.7196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3222   -2.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7419    1.4029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5406   -1.5496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3350    0.5273    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6175   -0.6740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1631    1.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1194   -1.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3996    0.9048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1171   -1.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9817    1.0824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3008   -1.2291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2970    0.0862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0145   -0.2329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1574    1.9452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4399   -2.0919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1598    1.2253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8773   -1.3720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5021    1.7234    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1982   -2.0477    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7332    1.2498    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0157   -1.3966    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 13  8  1  0  0  0  0
 14  7  1  0  0  0  0
 15  7  1  0  0  0  0
 16  8  1  0  0  0  0
 19  9  2  0  0  0  0
 19 10  1  0  0  0  0
 19 17  1  0  0  0  0
 20 11  2  0  0  0  0
 20 12  1  0  0  0  0
 20 18  1  0  0  0  0
 21 17  1  1  0  0  0
 22 18  1  1  0  0  0
 23 13  1  0  0  0  0
 24 14  1  0  0  0  0
 25 23  1  0  0  0  0
 26 24  1  0  0  0  0
 27 21  1  0  0  0  0
 28 22  1  0  0  0  0
 29 21  1  0  0  0  0
 29 25  2  0  0  0  0
 30 22  1  0  0  0  0
 30 26  2  0  0  0  0
 31 15  1  0  0  0  0
 31 24  1  0  0  0  0
 31 27  1  0  0  0  0
 32 16  1  0  0  0  0
 32 23  1  0  0  0  0
 32 28  1  0  0  0  0
 25 33  1  4  0  0  0
 26 34  1  4  0  0  0
 35 27  2  0  0  0  0
 36 28  2  0  0  0  0
 21 37  1  6  0  0  0
 22 38  1  6  0  0  0
 23 39  1  6  0  0  0
 24 40  1  6  0  0  0
M  END


  Mrv1652305142121472D          

 40 44  0  0  1  0            999 V2000
   -0.1285    3.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8426   -3.3297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2311    2.8972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6317    4.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1849   -3.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7400   -2.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6271    0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3446   -0.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4266    2.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2893    3.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247   -3.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798   -2.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1571    0.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4395   -0.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9210    0.6259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6385   -0.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8444    2.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380   -2.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1868    2.7196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3222   -2.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7419    1.4029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5406   -1.5496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3350    0.5273    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6175   -0.6740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1631    1.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1194   -1.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3996    0.9048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1171   -1.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9817    1.0824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3008   -1.2291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2970    0.0862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0145   -0.2329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1574    1.9452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4399   -2.0919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1598    1.2253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8773   -1.3720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5021    1.7234    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1982   -2.0477    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7332    1.2498    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0157   -1.3966    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 13  8  1  0  0  0  0
 14  7  1  0  0  0  0
 15  7  1  0  0  0  0
 16  8  1  0  0  0  0
 19  9  2  0  0  0  0
 19 10  1  0  0  0  0
 19 17  1  0  0  0  0
 20 11  2  0  0  0  0
 20 12  1  0  0  0  0
 20 18  1  0  0  0  0
 21 17  1  1  0  0  0
 22 18  1  1  0  0  0
 23 13  1  0  0  0  0
 24 14  1  0  0  0  0
 25 23  1  0  0  0  0
 26 24  1  0  0  0  0
 27 21  1  0  0  0  0
 28 22  1  0  0  0  0
 29 21  1  0  0  0  0
 29 25  2  0  0  0  0
 30 22  1  0  0  0  0
 30 26  2  0  0  0  0
 31 15  1  0  0  0  0
 31 24  1  0  0  0  0
 31 27  1  0  0  0  0
 32 16  1  0  0  0  0
 32 23  1  0  0  0  0
 32 28  1  0  0  0  0
 25 33  1  4  0  0  0
 26 34  1  4  0  0  0
 35 27  2  0  0  0  0
 36 28  2  0  0  0  0
 21 37  1  6  0  0  0
 22 38  1  6  0  0  0
 23 39  1  6  0  0  0
 24 40  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0001548

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12CCCN1C(=O)[C@]([H])(CC1=CC=CC=C1)N=C(O)[C@]1([H])CCCN1C(=O)[C@]([H])(CC1=CC=CC=C1)N=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C28H32N4O4/c33-25-23-13-8-16-32(23)28(36)22(18-20-11-5-2-6-12-20)30-26(34)24-14-7-15-31(24)27(35)21(29-25)17-19-9-3-1-4-10-19/h1-6,9-12,21-24H,7-8,13-18H2,(H,29,33)(H,30,34)/t21-,22-,23-,24-/m0/s1

> <INCHI_KEY>
QLPBAXRSKZBNQY-ZJZGAYNASA-N

> <FORMULA>
C28H32N4O4

> <MOLECULAR_WEIGHT>
488.588

> <EXACT_MASS>
488.242355526

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
51.29660772013662

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6S,12S,15S)-3,12-dibenzyl-5,14-dihydroxy-1,4,10,13-tetraazatricyclo[13.3.0.0^{6,10}]octadeca-4,13-diene-2,11-dione

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
2.51565530712176

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.584756186851331

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0453347347644253

> <JCHEM_PKA_STRONGEST_BASIC>
5.324162062530185

> <JCHEM_POLAR_SURFACE_AREA>
105.80000000000001

> <JCHEM_REFRACTIVITY>
134.84920000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S,12S,15S)-3,12-dibenzyl-5,14-dihydroxy-1,4,10,13-tetraazatricyclo[13.3.0.0^{6,10}]octadeca-4,13-diene-2,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-21         0                                  
HETATM    1  C   UNK     0      -0.240   6.936   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.439  -6.215   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.431   5.408   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.179   7.534   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.212  -7.145   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.248  -4.687   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.771   0.372   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.510  -0.646   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.796   4.478   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.407   6.605   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.793  -6.547   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.829  -4.089   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.160   0.854   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.420  -1.128   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.452   1.168   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.192  -1.442   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.443   4.147   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.818  -4.421   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.215   5.077   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.601  -5.019   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.252   2.619   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.009  -2.893   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.625   0.984   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.886  -1.258   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.304   2.212   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.956  -2.486   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.479   1.689   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.219  -1.963   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       1.832   2.020   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0       2.428  -2.294   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0       4.288   0.161   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0      -0.027  -0.435   0.000  0.00  0.00           N+0
HETATM   33  O   UNK     0      -0.294   3.631   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.554  -3.905   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       5.898   2.287   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -1.638  -2.561   0.000  0.00  0.00           O+0
HETATM   37  H   UNK     0       4.671   3.217   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.237  -3.822   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.369   2.333   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0       5.629  -2.607   0.000  0.00  0.00           H+0
CONECT    1    3    4                                                       
CONECT    2    5    6                                                       
CONECT    3    1    9                                                       
CONECT    4    1   10                                                       
CONECT    5    2   11                                                       
CONECT    6    2   12                                                       
CONECT    7   14   15                                                       
CONECT    8   13   16                                                       
CONECT    9    3   19                                                       
CONECT   10    4   19                                                       
CONECT   11    5   20                                                       
CONECT   12    6   20                                                       
CONECT   13    8   23                                                       
CONECT   14    7   24                                                       
CONECT   15    7   31                                                       
CONECT   16    8   32                                                       
CONECT   17   19   21                                                       
CONECT   18   20   22                                                       
CONECT   19    9   10   17                                                  
CONECT   20   11   12   18                                                  
CONECT   21   17   27   29   37                                             
CONECT   22   18   28   30   38                                             
CONECT   23   13   25   32   39                                             
CONECT   24   14   26   31   40                                             
CONECT   25   23   29   33                                                  
CONECT   26   24   30   34                                                  
CONECT   27   21   31   35                                                  
CONECT   28   22   32   36                                                  
CONECT   29   21   25                                                       
CONECT   30   22   26                                                       
CONECT   31   15   24   27                                                  
CONECT   32   16   23   28                                                  
CONECT   33   25                                                            
CONECT   34   26                                                            
CONECT   35   27                                                            
CONECT   36   28                                                            
CONECT   37   21                                                            
CONECT   38   22                                                            
CONECT   39   23                                                            
CONECT   40   24                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

Synonyms

Not Available

Molecular Formula

C₂₈H₃₂N₄O₄

Average Mass

488.588

Monoisotopic Mass

488.242355526

IUPAC Name

(3S,6S,12S,15S)-3,12-dibenzyl-5,14-dihydroxy-1,4,10,13-tetraazatricyclo[13.3.0.0^{6,10}]octadeca-4,13-diene-2,11-dione

Traditional Name

(3S,6S,12S,15S)-3,12-dibenzyl-5,14-dihydroxy-1,4,10,13-tetraazatricyclo[13.3.0.0^{6,10}]octadeca-4,13-diene-2,11-dione

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCCN1C(=O)[C@]([H])(CC1=CC=CC=C1)N=C(O)[C@]1([H])CCCN1C(=O)[C@]([H])(CC1=CC=CC=C1)N=C2O

InChI Identifier

InChI=1S/C28H32N4O4/c33-25-23-13-8-16-32(23)28(36)22(18-20-11-5-2-6-12-20)30-26(34)24-14-7-15-31(24)27(35)21(29-25)17-19-9-3-1-4-10-19/h1-6,9-12,21-24H,7-8,13-18H2,(H,29,33)(H,30,34)/t21-,22-,23-,24-/m0/s1

InChI Key

QLPBAXRSKZBNQY-ZJZGAYNASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cyclic peptides

Alternative Parents

Substituents

Cyclic alpha peptide
Macrolactam
Alpha-amino acid or derivatives
Monocyclic benzene moiety
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Secondary carboxylic acid amide
Lactam
Carboxamide group
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.054 g/L	ALOGPS
logP	2.14	ALOGPS
logP	2.52	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.05	ChemAxon
pKa (Strongest Basic)	5.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.8 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	134.85 m³·mol⁻¹	ChemAxon
Polarizability	51.3 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	200.1
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	63.2
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	539.0
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	476.7
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	493.5
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	186.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	2355.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	286.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	324.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	340.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	257.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	175.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	207.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	8.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	249.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	178.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	363.2
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1472.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1133.9

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Cyclo(Pro-Phe-Pro-Phe)_TMS_1	C[Si](C)(C)OC1=N[C@@H](CC2=CC=CC=C2)C(=O)N2CCC[C@H]2C(O)=N[C@@H](CC2=CC=CC=C2)C(=O)N2CCC[C@@H]12	standard non polar	2025-10-23	1510.9
Gas Chromatography	Cyclo(Pro-Phe-Pro-Phe)_TMS_2	C[Si](C)(C)OC1=N[C@@H](CC2=CC=CC=C2)C(=O)N2CCC[C@H]2C(O[Si](C)(C)C)=N[C@@H](CC2=CC=CC=C2)C(=O)N2CCC[C@@H]12	standard non polar	2025-10-23	1932.6
Gas Chromatography	Cyclo(Pro-Phe-Pro-Phe)_TMS_1	C[Si](C)(C)OC1=N[C@@H](CC2=CC=CC=C2)C(=O)N2CCC[C@H]2C(O)=N[C@@H](CC2=CC=CC=C2)C(=O)N2CCC[C@@H]12	standard polar	2025-10-23	2797.72
Gas Chromatography	Cyclo(Pro-Phe-Pro-Phe)_TMS_2	C[Si](C)(C)OC1=N[C@@H](CC2=CC=CC=C2)C(=O)N2CCC[C@H]2C(O[Si](C)(C)C)=N[C@@H](CC2=CC=CC=C2)C(=O)N2CCC[C@@H]12	standard polar	2025-10-23	2250.03

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human feces; Human	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78439577

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14863211

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Cyclo(Pro-Phe-Pro-Phe) (MMDBc0001548)

MOL for #<Metabolite:0x00007f9a86075288>

3D MOL for #<Metabolite:0x00007f9a86075288>

3D SDF for #<Metabolite:0x00007f9a86075288>

3D-SDF for #<Metabolite:0x00007f9a86075288>

PDB for #<Metabolite:0x00007f9a86075288>

3D PDB for #<Metabolite:0x00007f9a86075288>

SMILES for #<Metabolite:0x00007f9a86075288>

INCHI for #<Metabolite:0x00007f9a86075288>

Structure for #<Metabolite:0x00007f9a86075288>

3D Structure for #<Metabolite:0x00007f9a86075288>