Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 21:03:08 UTC

Update Date

2022-09-22 18:34:22 UTC

HMDB ID

HMDB0028959

Secondary Accession Numbers

HMDB28959

Metabolite Identification

Common Name

Lysylproline

Description

Lysylproline is a dipeptide composed of lysine and proline. It is an incomplete breakdown product of protein digestion or protein catabolism. Dipeptides are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Some dipeptides are known to have physiological or cell-signalling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.

Structure

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

HMDB0028959
     RDKit          3D
Lysylproline
 38 38  0  0  0  0  0  0  0  0999 V2000
    4.7325    0.0205    2.3358 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2947    0.3072    0.9781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7892    0.1294    0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4696    0.4434   -0.6148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0282    0.3236   -0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365   -1.0542   -0.7570 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1128   -2.0416   -1.5782 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0033   -1.0758   -1.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3955   -1.7807   -2.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9349   -0.3114   -0.3411 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6655    0.5337    0.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8597    0.2004    1.7234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9527   -0.2534    0.7956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3591   -0.1799   -0.5660 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7090    1.0252   -1.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8956    1.2885   -1.5905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177    1.8961   -1.7201 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5216    0.6399    2.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1034   -0.9707    2.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6007    1.3222    0.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8463   -0.3898    0.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5345   -0.8737    1.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193    0.8782    1.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1256   -0.1502   -1.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538    1.5043   -0.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9719    0.4849   -2.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4227    1.1151   -0.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5551   -1.3467    0.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7039   -2.9716   -1.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9794   -1.8879   -2.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7459    0.1448    1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807    1.5993    0.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1310    1.0785    2.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5743   -0.6580    2.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3418   -1.2528    1.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8103    0.4705    0.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6482   -1.1188   -1.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8761    2.9115   -1.7613 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 10  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  1
  7 29  1  0
  7 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  6
 17 38  1  0
M  END

      
  Mrv1652304062014002D          

 17 17  0  0  0  0            999 V2000
10001.0931 9999.6070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.378610000.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6633 9999.6070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.949310000.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2353 9999.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.519210000.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8050 9999.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.089010000.0195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6633 9998.7821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.378610000.8450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.1794 9998.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.9863 9998.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.3988 9999.3294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8468 9999.9424    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.018310000.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.405310001.3015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.803010001.0043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  2  0  0  0  0
  3  4  1  0  0  0  0
  3  9  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1 11  1  0  0  0  0
  1 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0028959

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H21N3O3/c12-6-2-1-4-8(13)10(15)14-7-3-5-9(14)11(16)17/h8-9H,1-7,12-13H2,(H,16,17)/t8-,9-/m0/s1

> <INCHI_KEY>
AIXUQKMMBQJZCU-IUCAKERBSA-N

> <FORMULA>
C11H21N3O3

> <MOLECULAR_WEIGHT>
243.307

> <EXACT_MASS>
243.158291548

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.059026720535066

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-[(2S)-2,6-diaminohexanoyl]pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-3.10

> <JCHEM_LOGP>
-3.3585842295490793

> <ALOGPS_LOGS>
-1.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6801513796941574

> <JCHEM_PKA_STRONGEST_BASIC>
10.212734160831241

> <JCHEM_POLAR_SURFACE_AREA>
109.64999999999999

> <JCHEM_REFRACTIVITY>
62.79600000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.07e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[(2S)-2,6-diaminohexanoyl]pyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0028959
     RDKit          3D
Lysylproline
 38 38  0  0  0  0  0  0  0  0999 V2000
    4.7325    0.0205    2.3358 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2947    0.3072    0.9781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7892    0.1294    0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4696    0.4434   -0.6148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0282    0.3236   -0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365   -1.0542   -0.7570 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1128   -2.0416   -1.5782 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0033   -1.0758   -1.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3955   -1.7807   -2.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9349   -0.3114   -0.3411 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6655    0.5337    0.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8597    0.2004    1.7234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9527   -0.2534    0.7956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3591   -0.1799   -0.5660 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7090    1.0252   -1.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8956    1.2885   -1.5905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177    1.8961   -1.7201 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5216    0.6399    2.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1034   -0.9707    2.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6007    1.3222    0.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8463   -0.3898    0.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5345   -0.8737    1.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193    0.8782    1.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1256   -0.1502   -1.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538    1.5043   -0.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9719    0.4849   -2.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4227    1.1151   -0.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5551   -1.3467    0.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7039   -2.9716   -1.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9794   -1.8879   -2.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7459    0.1448    1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807    1.5993    0.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1310    1.0785    2.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5743   -0.6580    2.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3418   -1.2528    1.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8103    0.4705    0.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6482   -1.1188   -1.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8761    2.9115   -1.7613 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 10  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  1
  7 29  1  0
  7 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  6
 17 38  1  0
M  END

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  N   UNK     0    8668.7078665.933   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0    8667.3738666.703   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8666.0388665.933   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8664.7058666.703   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8663.3738665.933   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8662.0368666.703   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8660.7038665.933   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0    8659.3668666.703   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0    8666.0388664.393   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0    8667.3738668.244   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8668.8688664.401   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8670.3748664.081   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8671.1448665.415   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8670.1148666.559   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8670.4348668.066   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8669.2908669.096   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8671.8998668.541   0.000  0.00  0.00           O+0
CONECT    1    2   11   14                                                  
CONECT    2    1    3   10                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    3                                                            
CONECT   10    2                                                            
CONECT   11   12    1                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    1   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0028959
HETATM    1  N1  UNL     1       4.732   0.020   2.336  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.295   0.307   0.978  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.789   0.129   0.815  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.470   0.443  -0.615  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.028   0.324  -0.958  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.437  -1.054  -0.757  1.00  0.00           C  
HETATM    7  N2  UNL     1       1.113  -2.042  -1.578  1.00  0.00           N  
HETATM    8  C6  UNL     1      -1.003  -1.076  -1.090  1.00  0.00           C  
HETATM    9  O1  UNL     1      -1.395  -1.781  -2.048  1.00  0.00           O  
HETATM   10  N3  UNL     1      -1.935  -0.311  -0.341  1.00  0.00           N  
HETATM   11  C7  UNL     1      -1.666   0.534   0.819  1.00  0.00           C  
HETATM   12  C8  UNL     1      -2.860   0.200   1.723  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.953  -0.253   0.796  1.00  0.00           C  
HETATM   14  C10 UNL     1      -3.359  -0.180  -0.566  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.709   1.025  -1.312  1.00  0.00           C  
HETATM   16  O2  UNL     1      -4.896   1.288  -1.591  1.00  0.00           O  
HETATM   17  O3  UNL     1      -2.718   1.896  -1.720  1.00  0.00           O  
HETATM   18  H1  UNL     1       5.522   0.640   2.623  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.103  -0.971   2.397  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.601   1.322   0.665  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.846  -0.390   0.294  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.534  -0.874   1.151  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.319   0.878   1.491  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.126  -0.150  -1.286  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.754   1.504  -0.791  1.00  0.00           H  
HETATM   26  H9  UNL     1       0.972   0.485  -2.081  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.423   1.115  -0.528  1.00  0.00           H  
HETATM   28  H11 UNL     1       0.555  -1.347   0.295  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.704  -2.972  -1.328  1.00  0.00           H  
HETATM   30  H13 UNL     1       0.979  -1.888  -2.586  1.00  0.00           H  
HETATM   31  H14 UNL     1      -0.746   0.145   1.302  1.00  0.00           H  
HETATM   32  H15 UNL     1      -1.681   1.599   0.611  1.00  0.00           H  
HETATM   33  H16 UNL     1      -3.131   1.078   2.356  1.00  0.00           H  
HETATM   34  H17 UNL     1      -2.574  -0.658   2.395  1.00  0.00           H  
HETATM   35  H18 UNL     1      -4.342  -1.253   1.081  1.00  0.00           H  
HETATM   36  H19 UNL     1      -4.810   0.470   0.885  1.00  0.00           H  
HETATM   37  H20 UNL     1      -3.648  -1.119  -1.118  1.00  0.00           H  
HETATM   38  H21 UNL     1      -2.876   2.911  -1.761  1.00  0.00           H  
CONECT    1    2   18   19
CONECT    2    3   20   21
CONECT    3    4   22   23
CONECT    4    5   24   25
CONECT    5    6   26   27
CONECT    6    7    8   28
CONECT    7   29   30
CONECT    8    9    9   10
CONECT   10   11   14
CONECT   11   12   31   32
CONECT   12   13   33   34
CONECT   13   14   35   36
CONECT   14   15   37
CONECT   15   16   16   17
CONECT   17   38
END

HMDB0028959
     RDKit          3D
Lysylproline
 38 38  0  0  0  0  0  0  0  0999 V2000
    4.7325    0.0205    2.3358 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2947    0.3072    0.9781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7892    0.1294    0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4696    0.4434   -0.6148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0282    0.3236   -0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365   -1.0542   -0.7570 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1128   -2.0416   -1.5782 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0033   -1.0758   -1.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3955   -1.7807   -2.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9349   -0.3114   -0.3411 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6655    0.5337    0.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8597    0.2004    1.7234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9527   -0.2534    0.7956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3591   -0.1799   -0.5660 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7090    1.0252   -1.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8956    1.2885   -1.5905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177    1.8961   -1.7201 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5216    0.6399    2.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1034   -0.9707    2.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6007    1.3222    0.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8463   -0.3898    0.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5345   -0.8737    1.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193    0.8782    1.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1256   -0.1502   -1.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538    1.5043   -0.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9719    0.4849   -2.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4227    1.1151   -0.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5551   -1.3467    0.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7039   -2.9716   -1.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9794   -1.8879   -2.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7459    0.1448    1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807    1.5993    0.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1310    1.0785    2.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5743   -0.6580    2.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3418   -1.2528    1.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8103    0.4705    0.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6482   -1.1188   -1.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8761    2.9115   -1.7613 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 10  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  1
  7 29  1  0
  7 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  6
 17 38  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
KP	ChEBI
L-Lys-L-pro	ChEBI
Lysyl-proline	ChEBI
K-p Dipeptide	HMDB
KP Dipeptide	HMDB
L-Lysyl-L-proline	HMDB
Lys-pro	HMDB
Lysine proline dipeptide	HMDB
Lysine-proline dipeptide	HMDB
N-L-Lysyl-L-proline	HMDB
N-Lysylproline	HMDB
Lysylproline	ChEBI

Chemical Formula

C₁₁H₂₁N₃O₃

Average Molecular Weight

243.307

Monoisotopic Molecular Weight

243.158291548

IUPAC Name

(2S)-1-[(2S)-2,6-diaminohexanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

(2S)-1-[(2S)-2,6-diaminohexanoyl]pyrrolidine-2-carboxylic acid

CAS Registry Number

52766-27-5

SMILES

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

InChI Identifier

InChI=1S/C11H21N3O3/c12-6-2-1-4-8(13)10(15)14-7-3-5-9(14)11(16)17/h8-9H,1-7,12-13H2,(H,16,17)/t8-,9-/m0/s1

InChI Key

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:74567 )

Ontology

Not Available

Feces (PMID: 27015276)

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

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-3.35	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	20.7 g/L	ALOGPS
logP	-3.1	ALOGPS
logP	-3.4	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.65 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	62.8 m³·mol⁻¹	ChemAxon
Polarizability	26.06 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]+	161.236	30932474
DeepCCS	[M-H]-	158.878	30932474
DeepCCS	[M-2H]-	191.764	30932474
DeepCCS	[M+Na]+	167.329	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lysylproline	NCCCC[C@H](N)C(=O)N1CCC[C@H]1C(O)=O	3009.4	Standard polar	33892256
Lysylproline	NCCCC[C@H](N)C(=O)N1CCC[C@H]1C(O)=O	2430.3	Standard non polar	33892256
Lysylproline	NCCCC[C@H](N)C(=O)N1CCC[C@H]1C(O)=O	2241.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lysylproline,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CCCCN	2210.5	Semi standard non polar	33892256
Lysylproline,1TMS,isomer #2	C[Si](C)(C)NCCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)O	2347.2	Semi standard non polar	33892256
Lysylproline,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)O	2281.6	Semi standard non polar	33892256
Lysylproline,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2270.5	Semi standard non polar	33892256
Lysylproline,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2366.1	Standard non polar	33892256
Lysylproline,2TMS,isomer #2	C[Si](C)(C)NCCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2344.4	Semi standard non polar	33892256
Lysylproline,2TMS,isomer #2	C[Si](C)(C)NCCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2390.4	Standard non polar	33892256
Lysylproline,2TMS,isomer #3	C[Si](C)(C)NCCCC[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	2394.6	Semi standard non polar	33892256
Lysylproline,2TMS,isomer #3	C[Si](C)(C)NCCCC[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	2460.8	Standard non polar	33892256
Lysylproline,2TMS,isomer #4	C[Si](C)(C)N(CCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C	2476.5	Semi standard non polar	33892256
Lysylproline,2TMS,isomer #4	C[Si](C)(C)N(CCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C	2496.6	Standard non polar	33892256
Lysylproline,2TMS,isomer #5	C[Si](C)(C)N([C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C	2388.4	Semi standard non polar	33892256
Lysylproline,2TMS,isomer #5	C[Si](C)(C)N([C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C	2404.4	Standard non polar	33892256
Lysylproline,3TMS,isomer #1	C[Si](C)(C)NCCCC[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2362.7	Semi standard non polar	33892256
Lysylproline,3TMS,isomer #1	C[Si](C)(C)NCCCC[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2514.3	Standard non polar	33892256
Lysylproline,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)N([Si](C)(C)C)[Si](C)(C)C	2405.4	Semi standard non polar	33892256
Lysylproline,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)N([Si](C)(C)C)[Si](C)(C)C	2470.1	Standard non polar	33892256
Lysylproline,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CCCCN([Si](C)(C)C)[Si](C)(C)C	2486.9	Semi standard non polar	33892256
Lysylproline,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CCCCN([Si](C)(C)C)[Si](C)(C)C	2522.8	Standard non polar	33892256
Lysylproline,3TMS,isomer #4	C[Si](C)(C)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	2518.9	Semi standard non polar	33892256
Lysylproline,3TMS,isomer #4	C[Si](C)(C)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	2567.6	Standard non polar	33892256
Lysylproline,3TMS,isomer #5	C[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2501.4	Semi standard non polar	33892256
Lysylproline,3TMS,isomer #5	C[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2557.7	Standard non polar	33892256
Lysylproline,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2544.7	Semi standard non polar	33892256
Lysylproline,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2585.8	Standard non polar	33892256
Lysylproline,4TMS,isomer #2	C[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2521.3	Semi standard non polar	33892256
Lysylproline,4TMS,isomer #2	C[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2595.8	Standard non polar	33892256
Lysylproline,4TMS,isomer #3	C[Si](C)(C)N(CCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2689.4	Semi standard non polar	33892256
Lysylproline,4TMS,isomer #3	C[Si](C)(C)N(CCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2662.4	Standard non polar	33892256
Lysylproline,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2743.9	Semi standard non polar	33892256
Lysylproline,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2671.7	Standard non polar	33892256
Lysylproline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CCCCN	2475.3	Semi standard non polar	33892256
Lysylproline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)O	2588.9	Semi standard non polar	33892256
Lysylproline,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)O	2542.9	Semi standard non polar	33892256
Lysylproline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2786.8	Semi standard non polar	33892256
Lysylproline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2734.8	Standard non polar	33892256
Lysylproline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2826.7	Semi standard non polar	33892256
Lysylproline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2795.4	Standard non polar	33892256
Lysylproline,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	2893.9	Semi standard non polar	33892256
Lysylproline,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	2828.6	Standard non polar	33892256
Lysylproline,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(CCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	2929.3	Semi standard non polar	33892256
Lysylproline,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(CCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	2874.5	Standard non polar	33892256
Lysylproline,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N([C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	2851.0	Semi standard non polar	33892256
Lysylproline,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N([C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	2809.1	Standard non polar	33892256
Lysylproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCCC[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	3092.9	Semi standard non polar	33892256
Lysylproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCCC[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	3019.2	Standard non polar	33892256
Lysylproline,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3089.6	Semi standard non polar	33892256
Lysylproline,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2992.8	Standard non polar	33892256
Lysylproline,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3151.1	Semi standard non polar	33892256
Lysylproline,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3073.1	Standard non polar	33892256
Lysylproline,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	3217.9	Semi standard non polar	33892256
Lysylproline,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	3124.3	Standard non polar	33892256
Lysylproline,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NCCCC[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	3214.8	Semi standard non polar	33892256
Lysylproline,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NCCCC[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	3104.0	Standard non polar	33892256
Lysylproline,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3444.6	Semi standard non polar	33892256
Lysylproline,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3265.6	Standard non polar	33892256
Lysylproline,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCCC[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	3431.0	Semi standard non polar	33892256
Lysylproline,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCCC[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	3250.2	Standard non polar	33892256
Lysylproline,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCCC[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)[Si](C)(C)C(C)(C)C	3535.2	Semi standard non polar	33892256
Lysylproline,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCCC[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)[Si](C)(C)C(C)(C)C	3366.1	Standard non polar	33892256
Lysylproline,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3750.2	Semi standard non polar	33892256
Lysylproline,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3462.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lysylproline 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 - Lysylproline 10V, Negative-QTOF	splash10-0006-0190000000-ad6a547d7c9f27703906	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lysylproline 20V, Negative-QTOF	splash10-03di-4910000000-04cbbbd92a8c083399e5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lysylproline 40V, Negative-QTOF	splash10-03dj-9500000000-53910ad96a9eb01239c8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lysylproline 10V, Positive-QTOF	splash10-0006-0190000000-f5a86c54b932dc0e1914	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lysylproline 20V, Positive-QTOF	splash10-003r-9650000000-9a709976cc4ebb9c216c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lysylproline 40V, Positive-QTOF	splash10-00di-9000000000-78f7f2bab78f3016e795	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

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
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
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

FDB111982

KNApSAcK ID

Not Available

Chemspider ID

149672

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

171204

PDB ID

Not Available

ChEBI ID

74567

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

Kieliszewski MJ, Leykam JF, Lamport DT: Trypsin cleaves lysylproline in a hydroxyproline-rich glycoprotein from Zea mays. Pept Res. 1989 May-Jun;2(3):246-8. [PubMed:2520761 ]
Nausch I, Heymann E: Substance P in human plasma is degraded by dipeptidyl peptidase IV, not by cholinesterase. J Neurochem. 1985 May;44(5):1354-7. [PubMed:2580948 ]
Katinas GS, Petriaeva MA: [The dynamics of the reparative regeneration of the rat epidermis exposed to lysylproline]. Morfologiia. 1992 May;102(5):106-12. [PubMed:1285287 ]
Karanewsky DS, Badia MC, Cushman DW, DeForrest JM, Dejneka T, Loots MJ, Perri MG, Petrillo EW Jr, Powell JR: (Phosphinyloxy)acyl amino acid inhibitors of angiotensin converting enzyme (ACE). 1. Discovery of (S)-1-[6-amino-2-[[hydroxy(4-phenylbutyl)phosphinyl]oxy]-1-oxohexyl]-L -proline a novel orally active inhibitor of ACE. J Med Chem. 1988 Jan;31(1):204-12. [PubMed:3336020 ]
Marino AM, Chong S, Dando SA, Kripalani KJ, Bathala MS, Morrison RA: Distribution of the dipeptide transporter system along the gastrointestinal tract of rats based on absorption of a stable and specific probe, SQ-29852. J Pharm Sci. 1996 Mar;85(3):282-6. [PubMed:8699329 ]

Showing metabocard for Lysylproline (HMDB0028959)

MOL for HMDB0028959 (Lysylproline)

3D MOL for HMDB0028959 (Lysylproline)

3D SDF for HMDB0028959 (Lysylproline)

3D-SDF for HMDB0028959 (Lysylproline)

PDB for HMDB0028959 (Lysylproline)

3D PDB for HMDB0028959 (Lysylproline)

SMILES for HMDB0028959 (Lysylproline)

INCHI for HMDB0028959 (Lysylproline)

Structure for HMDB0028959 (Lysylproline)

3D Structure for HMDB0028959 (Lysylproline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra