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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2008-10-29 15:21:35 UTC

Update Date

2021-09-14 15:45:02 UTC

HMDB ID

HMDB0011174

Secondary Accession Numbers

HMDB0028915
HMDB11174
HMDB28915

Metabolite Identification

Common Name

Isoleucylproline

Description

Isoleucylproline is a dipeptide composed of isoleucine and proline. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. It is found in urine (PMID: 3782411 ).

Structure

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

HMDB0011174
     RDKit          3D
Isoleucylproline
 36 36  0  0  0  0  0  0  0  0999 V2000
    1.1558   -2.0193   -0.8323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3630   -0.8693   -1.7932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0023    0.3043   -1.1687 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3575   -0.0503   -0.5886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1849    1.2166   -0.3202 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1743    2.2293    0.1167 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    0.6333    0.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1566    0.5066    1.9449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8261    0.1852    0.8342 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5197   -0.4300    1.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6309   -1.2719    1.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4844   -1.1199   -0.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8255    0.2368   -0.1953 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7965    1.3366   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7125    1.4696   -0.8484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7336    2.2053    1.0542 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2758   -2.6260   -1.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1299   -1.6581    0.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0447   -2.7042   -0.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4570   -0.6373   -2.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0812   -1.2765   -2.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2989    0.9820   -2.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8520    0.9073   -0.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9623   -0.4609   -1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3154   -0.7865    0.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375    1.7218   -0.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8764    2.6963    0.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667    2.8254   -0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7451   -1.0351    2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9380    0.3523    2.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4516   -2.3638    1.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6287   -0.9919    1.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9210   -1.9282   -0.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5221   -1.0267   -0.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3479    0.2811   -1.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0318    3.1659    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  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 16  1  0
 13  9  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  6
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  6
  6 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  6
 16 36  1  0
M  END

      
  Mrv1652305161919552D          

 16 16  0  0  0  0            999 V2000
 2500.3943 2500.4331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6794 2500.8449    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2498.9582 2500.4454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2498.2434 2500.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5223 2500.4577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9582 2499.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6794 2501.6704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.1093 2500.8449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7627 2499.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4776 2499.1018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7627 2500.3411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3766 2499.5958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.7093 2499.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9642 2498.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7892 2498.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0441 2499.1109    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  2  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  6  0  0  0
  3  4  1  0  0  0  0
  3  6  1  1  0  0  0
  4  5  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 16  9  1  6  0  0  0
  1 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011174

> <DATABASE_NAME>
hmdb

> <SMILES>
CC[C@H](C)[C@H](N)C(=O)N1CCC[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H20N2O3/c1-3-7(2)9(12)10(14)13-6-4-5-8(13)11(15)16/h7-9H,3-6,12H2,1-2H3,(H,15,16)/t7-,8-,9-/m0/s1

> <INCHI_KEY>
BBIXOODYWPFNDT-CIUDSAMLSA-N

> <FORMULA>
C11H20N2O3

> <MOLECULAR_WEIGHT>
228.292

> <EXACT_MASS>
228.147392512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
24.283770819739253

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-[(2S,3S)-2-amino-3-methylpentanoyl]pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-0.45

> <JCHEM_LOGP>
-1.7752702079774902

> <ALOGPS_LOGS>
-0.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9154771752947966

> <JCHEM_PKA_STRONGEST_BASIC>
8.49948149969245

> <JCHEM_POLAR_SURFACE_AREA>
83.63000000000001

> <JCHEM_REFRACTIVITY>
59.08040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.03e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[(2S,3S)-2-amino-3-methylpentanoyl]pyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011174
     RDKit          3D
Isoleucylproline
 36 36  0  0  0  0  0  0  0  0999 V2000
    1.1558   -2.0193   -0.8323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3630   -0.8693   -1.7932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0023    0.3043   -1.1687 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3575   -0.0503   -0.5886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1849    1.2166   -0.3202 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1743    2.2293    0.1167 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    0.6333    0.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1566    0.5066    1.9449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8261    0.1852    0.8342 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5197   -0.4300    1.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6309   -1.2719    1.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4844   -1.1199   -0.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8255    0.2368   -0.1953 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7965    1.3366   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7125    1.4696   -0.8484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7336    2.2053    1.0542 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2758   -2.6260   -1.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1299   -1.6581    0.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0447   -2.7042   -0.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4570   -0.6373   -2.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0812   -1.2765   -2.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2989    0.9820   -2.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8520    0.9073   -0.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9623   -0.4609   -1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3154   -0.7865    0.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375    1.7218   -0.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8764    2.6963    0.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667    2.8254   -0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7451   -1.0351    2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9380    0.3523    2.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4516   -2.3638    1.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6287   -0.9919    1.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9210   -1.9282   -0.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5221   -1.0267   -0.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3479    0.2811   -1.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0318    3.1659    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  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 16  1  0
 13  9  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  6
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  6
  6 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  6
 16 36  1  0
M  END

HEADER    PROTEIN                                 16-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-19         0                                  
HETATM    1  C   UNK     0    4667.4034667.475   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4666.0684668.244   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    4664.7224667.498   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4663.3884668.267   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4662.0424667.521   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4664.7224665.957   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    4666.0684669.785   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0    4668.7374668.244   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    4669.9574665.762   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    4671.2924664.990   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    4669.9574667.303   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0    4667.3704665.912   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    4666.1244665.007   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4666.6004663.542   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4668.1404663.542   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4668.6164665.007   0.000  0.00  0.00           C+0
CONECT    1    2    8   12                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3                                                            
CONECT    7    2                                                            
CONECT    8    1                                                            
CONECT    9   10   11   16                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12   13   16    1                                                  
CONECT   13   14   12                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12    9                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0011174
HETATM    1  C1  UNL     1       1.156  -2.019  -0.832  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.363  -0.869  -1.793  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.002   0.304  -1.169  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.358  -0.050  -0.589  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.185   1.217  -0.320  1.00  0.00           C  
HETATM    6  N1  UNL     1       2.174   2.229   0.117  1.00  0.00           N  
HETATM    7  C6  UNL     1       0.523   0.633   0.841  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.157   0.507   1.945  1.00  0.00           O  
HETATM    9  N2  UNL     1      -0.826   0.185   0.834  1.00  0.00           N  
HETATM   10  C7  UNL     1      -1.520  -0.430   1.981  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.631  -1.272   1.403  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.484  -1.120  -0.096  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.825   0.237  -0.195  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.796   1.337  -0.002  1.00  0.00           C  
HETATM   15  O2  UNL     1      -3.713   1.470  -0.848  1.00  0.00           O  
HETATM   16  O3  UNL     1      -2.734   2.205   1.054  1.00  0.00           O  
HETATM   17  H1  UNL     1       0.276  -2.626  -1.080  1.00  0.00           H  
HETATM   18  H2  UNL     1       1.130  -1.658   0.213  1.00  0.00           H  
HETATM   19  H3  UNL     1       2.045  -2.704  -0.874  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.457  -0.637  -2.392  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.081  -1.276  -2.578  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.299   0.982  -2.060  1.00  0.00           H  
HETATM   23  H7  UNL     1       3.852   0.907  -0.291  1.00  0.00           H  
HETATM   24  H8  UNL     1       3.962  -0.461  -1.423  1.00  0.00           H  
HETATM   25  H9  UNL     1       3.315  -0.786   0.211  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.437   1.722  -0.963  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.876   2.696   0.976  1.00  0.00           H  
HETATM   28  H12 UNL     1       2.467   2.825  -0.660  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.745  -1.035   2.500  1.00  0.00           H  
HETATM   30  H14 UNL     1      -1.938   0.352   2.644  1.00  0.00           H  
HETATM   31  H15 UNL     1      -2.452  -2.364   1.614  1.00  0.00           H  
HETATM   32  H16 UNL     1      -3.629  -0.992   1.771  1.00  0.00           H  
HETATM   33  H17 UNL     1      -1.921  -1.928  -0.557  1.00  0.00           H  
HETATM   34  H18 UNL     1      -3.522  -1.027  -0.530  1.00  0.00           H  
HETATM   35  H19 UNL     1      -1.348   0.281  -1.190  1.00  0.00           H  
HETATM   36  H20 UNL     1      -3.032   3.166   0.952  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4    5   22
CONECT    4   23   24   25
CONECT    5    6    7   26
CONECT    6   27   28
CONECT    7    8    8    9
CONECT    9   10   13
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   33   34
CONECT   13   14   35
CONECT   14   15   15   16
CONECT   16   36
END

HMDB0011174
     RDKit          3D
Isoleucylproline
 36 36  0  0  0  0  0  0  0  0999 V2000
    1.1558   -2.0193   -0.8323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3630   -0.8693   -1.7932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0023    0.3043   -1.1687 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3575   -0.0503   -0.5886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1849    1.2166   -0.3202 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1743    2.2293    0.1167 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    0.6333    0.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1566    0.5066    1.9449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8261    0.1852    0.8342 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5197   -0.4300    1.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6309   -1.2719    1.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4844   -1.1199   -0.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8255    0.2368   -0.1953 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7965    1.3366   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7125    1.4696   -0.8484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7336    2.2053    1.0542 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2758   -2.6260   -1.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1299   -1.6581    0.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0447   -2.7042   -0.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4570   -0.6373   -2.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0812   -1.2765   -2.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2989    0.9820   -2.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8520    0.9073   -0.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9623   -0.4609   -1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3154   -0.7865    0.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375    1.7218   -0.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8764    2.6963    0.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667    2.8254   -0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7451   -1.0351    2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9380    0.3523    2.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4516   -2.3638    1.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6287   -0.9919    1.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9210   -1.9282   -0.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5221   -1.0267   -0.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3479    0.2811   -1.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0318    3.1659    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  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 16  1  0
 13  9  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  6
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  6
  6 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  6
 16 36  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
IP	ChEBI
Isoleucyl-proline	ChEBI
L-Ile-L-pro	ChEBI
1-L-Isoleucyl-L-proline	HMDB
1-L-Isoleucyl-proline	HMDB
I-p dipeptide	HMDB
IP dipeptide	HMDB
Ile-pro	HMDB
Isoleucine proline dipeptide	HMDB
Isoleucine-proline dipeptide	HMDB
L-Isoleucyl-L-proline	HMDB
Isoleucylproline	ChEBI
IP dipeptide	HMDB

Chemical Formula

C₁₁H₂₀N₂O₃

Average Molecular Weight

228.292

Monoisotopic Molecular Weight

228.147392512

IUPAC Name

(2S)-1-[(2S,3S)-2-amino-3-methylpentanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

(2S)-1-[(2S,3S)-2-amino-3-methylpentanoyl]pyrrolidine-2-carboxylic acid

CAS Registry Number

37462-92-3

SMILES

CC[C@H](C)[C@H](N)C(=O)N1CCC[C@H]1C(O)=O

InChI Identifier

InChI=1S/C11H20N2O3/c1-3-7(2)9(12)10(14)13-6-4-5-8(13)11(15)16/h7-9H,3-6,12H2,1-2H3,(H,15,16)/t7-,8-,9-/m0/s1

InChI Key

BBIXOODYWPFNDT-CIUDSAMLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Isoleucine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Proline or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Azacycle
Organoheterocyclic compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic oxide
Organopnictogen compound
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Amine
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:74076 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0011174)

Excreta

Biofluid or Excreta

Urine (PMID: 21465502)

Source

Endogenous

Endogenous (HMDB: HMDB0011174)

Exogenous

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

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	50.3 g/L	ALOGPS
logP	-0.45	ALOGPS
logP	-1.8	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	3.92	ChemAxon
pKa (Strongest Basic)	8.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.63 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	59.08 m³·mol⁻¹	ChemAxon
Polarizability	24.28 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	161.28	30932474
DeepCCS	[M-H]-	158.922	30932474
DeepCCS	[M-2H]-	191.808	30932474
DeepCCS	[M+Na]+	167.373	30932474

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. Predicted by Afia on May 17, 2022.	1.93 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7934 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.35 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	263.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1010.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	211.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	104.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	158.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	69.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	280.9 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	310.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	573.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	649.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	246.7 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	944.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	176.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	217.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	435.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	400.7 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	176.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoleucylproline	CC[C@H](C)[C@H](N)C(=O)N1CCC[C@H]1C(O)=O	2799.4	Standard polar	33892256
Isoleucylproline	CC[C@H](C)[C@H](N)C(=O)N1CCC[C@H]1C(O)=O	1977.3	Standard non polar	33892256
Isoleucylproline	CC[C@H](C)[C@H](N)C(=O)N1CCC[C@H]1C(O)=O	1990.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isoleucylproline,1TMS,isomer #1	CC[C@H](C)[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	1902.2	Semi standard non polar	33892256
Isoleucylproline,1TMS,isomer #2	CC[C@H](C)[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	1931.9	Semi standard non polar	33892256
Isoleucylproline,2TMS,isomer #1	CC[C@H](C)[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	1943.1	Semi standard non polar	33892256
Isoleucylproline,2TMS,isomer #1	CC[C@H](C)[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2009.2	Standard non polar	33892256
Isoleucylproline,2TMS,isomer #1	CC[C@H](C)[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2452.1	Standard polar	33892256
Isoleucylproline,2TMS,isomer #2	CC[C@H](C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2051.9	Semi standard non polar	33892256
Isoleucylproline,2TMS,isomer #2	CC[C@H](C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2065.3	Standard non polar	33892256
Isoleucylproline,2TMS,isomer #2	CC[C@H](C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2598.4	Standard polar	33892256
Isoleucylproline,3TMS,isomer #1	CC[C@H](C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2102.2	Semi standard non polar	33892256
Isoleucylproline,3TMS,isomer #1	CC[C@H](C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2126.1	Standard non polar	33892256
Isoleucylproline,3TMS,isomer #1	CC[C@H](C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2279.9	Standard polar	33892256
Isoleucylproline,1TBDMS,isomer #1	CC[C@H](C)[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2136.6	Semi standard non polar	33892256
Isoleucylproline,1TBDMS,isomer #2	CC[C@H](C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	2164.9	Semi standard non polar	33892256
Isoleucylproline,2TBDMS,isomer #1	CC[C@H](C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2412.7	Semi standard non polar	33892256
Isoleucylproline,2TBDMS,isomer #1	CC[C@H](C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2403.3	Standard non polar	33892256
Isoleucylproline,2TBDMS,isomer #1	CC[C@H](C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2637.2	Standard polar	33892256
Isoleucylproline,2TBDMS,isomer #2	CC[C@H](C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2474.9	Semi standard non polar	33892256
Isoleucylproline,2TBDMS,isomer #2	CC[C@H](C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2479.1	Standard non polar	33892256
Isoleucylproline,2TBDMS,isomer #2	CC[C@H](C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2714.5	Standard polar	33892256
Isoleucylproline,3TBDMS,isomer #1	CC[C@H](C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2743.0	Semi standard non polar	33892256
Isoleucylproline,3TBDMS,isomer #1	CC[C@H](C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2681.2	Standard non polar	33892256
Isoleucylproline,3TBDMS,isomer #1	CC[C@H](C)[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2609.0	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Asthma	21465502	details

Associated Disorders and Diseases

Disease References

Asthma
Mattarucchi E, Baraldi E, Guillou C: Metabolomics applied to urine samples in childhood asthma; differentiation between asthma phenotypes and identification of relevant metabolites. Biomed Chromatogr. 2012 Jan;26(1):89-94. doi: 10.1002/bmc.1631. Epub 2011 Apr 4. [PubMed:21465502 ]

Associated OMIM IDs

600807 (Asthma)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

392673

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

444876

PDB ID

Not Available

ChEBI ID

74076

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

Jandke J, Spiteller G: Dipeptide analysis in human urine. J Chromatogr. 1986 Oct 31;382:39-45. [PubMed:3782411 ]

Showing metabocard for Isoleucylproline (HMDB0011174)

MOL for HMDB0011174 (Isoleucylproline)

3D MOL for HMDB0011174 (Isoleucylproline)

3D SDF for HMDB0011174 (Isoleucylproline)

3D-SDF for HMDB0011174 (Isoleucylproline)

PDB for HMDB0011174 (Isoleucylproline)

3D PDB for HMDB0011174 (Isoleucylproline)

SMILES for HMDB0011174 (Isoleucylproline)

INCHI for HMDB0011174 (Isoleucylproline)

Structure for HMDB0011174 (Isoleucylproline)

3D Structure for HMDB0011174 (Isoleucylproline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized