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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2008-10-29 15:23:53 UTC

Update Date

2022-09-22 18:34:20 UTC

HMDB ID

HMDB0011180

Secondary Accession Numbers

HMDB11180

Metabolite Identification

Common Name

Prolylproline

Description

Prolylproline, also known as P-P or L-pro-L-pro, 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. Prolylproline is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on Prolylproline.

Structure

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

HMDB0011180
     RDKit          3D
Prolylproline
 31 32  0  0  0  0  0  0  0  0999 V2000
   -2.4326   -0.1424    2.5572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8003   -0.6585    1.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3433   -1.9545    1.7534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6004    0.1799    0.3964 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9585    0.4772   -0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9513   -0.0070   -1.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7312   -0.8915   -1.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8425   -0.5045   -0.6225 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5330   -0.7524   -0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615   -1.3907   -1.5388 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4567   -0.3511    0.5207 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4944    1.1487    0.5682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9445    1.5576    0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6153    0.3078   -0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -0.8025    0.2854 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0462   -2.2716    2.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1172    1.1165    0.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7805    0.0475    0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1077    1.5973   -0.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8774   -0.5864   -1.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9037    0.8534   -2.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3126   -0.7152   -2.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9940   -1.9636   -1.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1158   -0.7752    1.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0933    1.5748    1.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654    1.6330   -0.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0860    2.3985   -0.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3406    1.8977    1.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7781    0.3570   -1.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6264    0.2346    0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8818   -1.6142   -0.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  8  4  1  0
 15 11  1  0
  3 16  1  0
  4 17  1  1
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
 11 24  1  1
 12 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
M  END


  Mrv1652305161920212D          

 15 16  0  0  0  0            999 V2000
 2499.9702 2499.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9702 2500.7534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.3663 2500.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.0807 2501.2567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.6519 2501.2567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5840 2500.0091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2497.9166 2499.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.1715 2498.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9965 2498.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2514 2499.5241    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2501.3496 2500.0091    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2500.6822 2499.5241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.9371 2498.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7621 2498.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.0170 2499.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  0  0  0  0
 11 15  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10  1  1  6  0  0  0
 11  3  1  6  0  0  0
  1 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011180

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N2O3/c13-9(7-3-1-5-11-7)12-6-2-4-8(12)10(14)15/h7-8,11H,1-6H2,(H,14,15)/t7-,8-/m0/s1

> <INCHI_KEY>
RWCOTTLHDJWHRS-YUMQZZPRSA-N

> <FORMULA>
C10H16N2O3

> <MOLECULAR_WEIGHT>
212.249

> <EXACT_MASS>
212.116092383

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
21.691547630784726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-[(2S)-pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-2.34

> <JCHEM_LOGP>
-2.833168522112887

> <ALOGPS_LOGS>
-0.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6971759858624726

> <JCHEM_PKA_STRONGEST_BASIC>
9.817472044231536

> <JCHEM_POLAR_SURFACE_AREA>
69.63999999999999

> <JCHEM_REFRACTIVITY>
53.0508

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.16e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[(2S)-pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011180
     RDKit          3D
Prolylproline
 31 32  0  0  0  0  0  0  0  0999 V2000
   -2.4326   -0.1424    2.5572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8003   -0.6585    1.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3433   -1.9545    1.7534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6004    0.1799    0.3964 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9585    0.4772   -0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9513   -0.0070   -1.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7312   -0.8915   -1.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8425   -0.5045   -0.6225 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5330   -0.7524   -0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615   -1.3907   -1.5388 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4567   -0.3511    0.5207 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4944    1.1487    0.5682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9445    1.5576    0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6153    0.3078   -0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -0.8025    0.2854 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0462   -2.2716    2.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1172    1.1165    0.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7805    0.0475    0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1077    1.5973   -0.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8774   -0.5864   -1.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9037    0.8534   -2.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3126   -0.7152   -2.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9940   -1.9636   -1.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1158   -0.7752    1.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0933    1.5748    1.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654    1.6330   -0.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0860    2.3985   -0.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3406    1.8977    1.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7781    0.3570   -1.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6264    0.2346    0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8818   -1.6142   -0.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  8  4  1  0
 15 11  1  0
  3 16  1  0
  4 17  1  1
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
 11 24  1  1
 12 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
M  END

HEADER    PROTEIN                                 16-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-19         0                                  
HETATM    1  C   UNK     0    4666.6114666.533   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    4666.6114668.073   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    4669.2174668.245   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    4670.5514669.013   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    4667.8844669.013   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0    4664.0234666.684   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0    4662.7784665.778   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    4663.2534664.314   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    4664.7934664.314   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    4665.2694665.778   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4669.1864666.684   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0    4667.9404665.778   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    4668.4164664.314   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4669.9564664.314   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4670.4324665.778   0.000  0.00  0.00           C+0
CONECT    1    2   10   12                                                  
CONECT    2    1                                                            
CONECT    3    4    5   11                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    7   10                                                       
CONECT    7    8    6                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6    1                                                  
CONECT   11   15   12    3                                                  
CONECT   12   11   13    1                                                  
CONECT   13   14   12                                                       
CONECT   14   13   15                                                       
CONECT   15   11   14                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0011180
HETATM    1  O1  UNL     1      -2.433  -0.142   2.557  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.800  -0.659   1.605  1.00  0.00           C  
HETATM    3  O2  UNL     1      -1.343  -1.955   1.753  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.600   0.180   0.396  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.958   0.477  -0.153  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.951  -0.007  -1.556  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.731  -0.892  -1.693  1.00  0.00           C  
HETATM    8  N1  UNL     1      -0.843  -0.505  -0.622  1.00  0.00           N  
HETATM    9  C6  UNL     1       0.533  -0.752  -0.563  1.00  0.00           C  
HETATM   10  O3  UNL     1       1.061  -1.391  -1.539  1.00  0.00           O  
HETATM   11  C7  UNL     1       1.457  -0.351   0.521  1.00  0.00           C  
HETATM   12  C8  UNL     1       1.494   1.149   0.568  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.944   1.558   0.428  1.00  0.00           C  
HETATM   14  C10 UNL     1       3.615   0.308  -0.083  1.00  0.00           C  
HETATM   15  N2  UNL     1       2.807  -0.803   0.285  1.00  0.00           N  
HETATM   16  H1  UNL     1      -1.046  -2.272   2.668  1.00  0.00           H  
HETATM   17  H2  UNL     1      -1.117   1.117   0.757  1.00  0.00           H  
HETATM   18  H3  UNL     1      -3.780   0.048   0.463  1.00  0.00           H  
HETATM   19  H4  UNL     1      -3.108   1.597  -0.149  1.00  0.00           H  
HETATM   20  H5  UNL     1      -3.877  -0.586  -1.757  1.00  0.00           H  
HETATM   21  H6  UNL     1      -2.904   0.853  -2.268  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.313  -0.715  -2.698  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.994  -1.964  -1.606  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.116  -0.775   1.485  1.00  0.00           H  
HETATM   25  H10 UNL     1       1.093   1.575   1.519  1.00  0.00           H  
HETATM   26  H11 UNL     1       0.965   1.633  -0.278  1.00  0.00           H  
HETATM   27  H12 UNL     1       3.086   2.398  -0.283  1.00  0.00           H  
HETATM   28  H13 UNL     1       3.341   1.898   1.403  1.00  0.00           H  
HETATM   29  H14 UNL     1       3.778   0.357  -1.192  1.00  0.00           H  
HETATM   30  H15 UNL     1       4.626   0.235   0.371  1.00  0.00           H  
HETATM   31  H16 UNL     1       2.882  -1.614  -0.340  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   16
CONECT    4    5    8   17
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8   22   23
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   15   24
CONECT   12   13   25   26
CONECT   13   14   27   28
CONECT   14   15   29   30
CONECT   15   31
END

HMDB0011180
     RDKit          3D
Prolylproline
 31 32  0  0  0  0  0  0  0  0999 V2000
   -2.4326   -0.1424    2.5572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8003   -0.6585    1.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3433   -1.9545    1.7534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6004    0.1799    0.3964 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9585    0.4772   -0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9513   -0.0070   -1.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7312   -0.8915   -1.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8425   -0.5045   -0.6225 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5330   -0.7524   -0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615   -1.3907   -1.5388 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4567   -0.3511    0.5207 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4944    1.1487    0.5682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9445    1.5576    0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6153    0.3078   -0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -0.8025    0.2854 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0462   -2.2716    2.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1172    1.1165    0.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7805    0.0475    0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1077    1.5973   -0.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8774   -0.5864   -1.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9037    0.8534   -2.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3126   -0.7152   -2.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9940   -1.9636   -1.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1158   -0.7752    1.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0933    1.5748    1.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654    1.6330   -0.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0860    2.3985   -0.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3406    1.8977    1.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7781    0.3570   -1.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6264    0.2346    0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8818   -1.6142   -0.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  8  4  1  0
 15 11  1  0
  3 16  1  0
  4 17  1  1
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
 11 24  1  1
 12 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
L-Pro-L-pro	ChEBI
P-P	ChEBI
PP	ChEBI
Prolyl-proline	HMDB
D-Pro-L-pro	HMDB
1-L-Prolyl-L-proline	HMDB
Di-L-proline	HMDB
L-Proline dipeptide	HMDB
L-Prolyl-L-proline	HMDB
N-[(S)-Prolyl]-(S)-proline	HMDB
NSC 97940	HMDB
p-p Dipeptide	HMDB
PP Dipeptide	HMDB
Pro-pro	HMDB
Proline proline dipeptide	HMDB
Proline-proline dipeptide	HMDB
Prolylproline	ChEBI

Chemical Formula

C₁₀H₁₆N₂O₃

Average Molecular Weight

212.249

Monoisotopic Molecular Weight

212.116092383

IUPAC Name

(2S)-1-[(2S)-pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylic acid

Traditional Name

(2S)-1-[(2S)-pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylic acid

CAS Registry Number

20488-28-2

SMILES

OC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1

InChI Identifier

InChI=1S/C10H16N2O3/c13-9(7-3-1-5-11-7)12-6-2-4-8(12)10(14)15/h7-8,11H,1-6H2,(H,14,15)/t7-,8-/m0/s1

InChI Key

RWCOTTLHDJWHRS-YUMQZZPRSA-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
Pyrrolidine-2-carboxamide
Pyrrolidine carboxylic acid or derivatives
Tertiary carboxylic acid amide
Pyrrolidine
Amino acid or derivatives
Carboxamide group
Amino acid
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Secondary amine
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Amine
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:73646 )

Ontology

Not Available

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	31.6 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-2.8	ChemAxon
logS	-0.83	ALOGPS
pKa (Strongest Acidic)	3.7	ChemAxon
pKa (Strongest Basic)	9.82	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.64 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	53.05 m³·mol⁻¹	ChemAxon
Polarizability	21.69 Å³	ChemAxon
Number of Rings	2	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]+	144.969	30932474
DeepCCS	[M-H]-	142.622	30932474
DeepCCS	[M-2H]-	176.101	30932474
DeepCCS	[M+Na]+	150.881	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prolylproline	OC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1	3009.2	Standard polar	33892256
Prolylproline	OC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1	2001.5	Standard non polar	33892256
Prolylproline	OC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1	2021.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Prolylproline,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1	1961.8	Semi standard non polar	33892256
Prolylproline,1TMS,isomer #2	C[Si](C)(C)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)O	1919.4	Semi standard non polar	33892256
Prolylproline,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1[Si](C)(C)C	1958.7	Semi standard non polar	33892256
Prolylproline,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1[Si](C)(C)C	2031.6	Standard non polar	33892256
Prolylproline,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1[Si](C)(C)C	2577.4	Standard polar	33892256
Prolylproline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1	2206.8	Semi standard non polar	33892256
Prolylproline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)O	2183.7	Semi standard non polar	33892256
Prolylproline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C	2434.5	Semi standard non polar	33892256
Prolylproline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C	2438.9	Standard non polar	33892256
Prolylproline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C	2767.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Prolylproline 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 - Prolylproline 10V, Positive-QTOF	splash10-03dj-4980000000-e8d5c1618b56c871969d	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prolylproline 20V, Positive-QTOF	splash10-00di-9200000000-d8378dae97558beccb90	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prolylproline 40V, Positive-QTOF	splash10-00dl-9000000000-9944e19e0bb7ae61e1b9	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prolylproline 10V, Negative-QTOF	splash10-03xr-0980000000-4faca44abdad94b523ae	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prolylproline 20V, Negative-QTOF	splash10-02t9-4920000000-7c6ac1de440883b8596a	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prolylproline 40V, Negative-QTOF	splash10-02fy-9300000000-a69b06ea9a41728d8b8f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prolylproline 10V, Negative-QTOF	splash10-03di-2090000000-cd8be1510aa3dbbd8fc0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prolylproline 20V, Negative-QTOF	splash10-00kb-9000000000-98547b8998d6837b3c7a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prolylproline 40V, Negative-QTOF	splash10-00ko-9200000000-4b258fb8735b28f02791	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prolylproline 10V, Positive-QTOF	splash10-01vk-9230000000-91ed4a6370b535be70e8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prolylproline 20V, Positive-QTOF	splash10-00di-9100000000-c66229844d56f1d25525	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prolylproline 40V, Positive-QTOF	splash10-00di-9000000000-ae5d84e340d05c6b49e3	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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
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

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9797341

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11622593

PDB ID

Not Available

ChEBI ID

73646

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 Prolylproline (HMDB0011180)

MOL for HMDB0011180 (Prolylproline)

3D MOL for HMDB0011180 (Prolylproline)

3D SDF for HMDB0011180 (Prolylproline)

3D-SDF for HMDB0011180 (Prolylproline)

PDB for HMDB0011180 (Prolylproline)

3D PDB for HMDB0011180 (Prolylproline)

SMILES for HMDB0011180 (Prolylproline)

INCHI for HMDB0011180 (Prolylproline)

Structure for HMDB0011180 (Prolylproline)

3D Structure for HMDB0011180 (Prolylproline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra