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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 21:02:49 UTC

Update Date

2021-09-14 15:19:03 UTC

HMDB ID

HMDB0028871

Secondary Accession Numbers

HMDB28871

Metabolite Identification

Common Name

Hydroxyprolyl-Proline

Description

Hydroxyprolyl-Proline is a dipeptide composed of hydroxyproline 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. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite.

Structure

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

HMDB0028871
     RDKit          3D
Hydroxyprolyl-Proline
 32 33  0  0  0  0  0  0  0  0999 V2000
   -0.9405    2.4080    0.1278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0039    2.0219   -0.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0053    2.9147   -0.6925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1650    0.6039   -0.7473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3484   -0.0312   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8388   -1.4391    0.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3990   -1.1360    0.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0154   -0.1960   -0.3873 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2730   -0.0722   -0.9580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5162    0.7897   -1.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4178   -0.9314   -0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7591   -0.7655    0.9233 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8130    0.3086    0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7206    0.1613    1.9522 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4639    0.1649   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6113   -0.6294   -1.2699 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9438    3.9127   -0.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3780    0.5359   -1.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2583   -0.0215   -0.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5178    0.4161    0.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7426   -1.9969   -0.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3959   -1.9927    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5032   -0.5833    1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7826   -2.0300    0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0985   -1.9813   -0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8823   -0.4607    1.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1978   -1.7199    1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2861    1.2924    0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0075    1.0878    2.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385    1.1586   -0.9513 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4920   -0.2846   -0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0609   -1.5050   -1.6321 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
 13 15  1  0
 15 16  1  0
  8  4  1  0
 16 11  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
M  END


  Mrv1652304062013452D          

 16 17  0  0  0  0            999 V2000
    0.7324   -0.2349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0179   -0.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6965   -0.2349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0179   -1.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6854   -1.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4304   -2.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3946   -2.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6495   -1.9573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4341   -1.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6056   -0.8954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0472   -2.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9610   -3.0749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7147   -3.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2667   -2.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0872   -2.8836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8542   -2.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  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
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  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
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 11 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0028871

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1CNC(C1)C(=O)N1CCCC1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N2O4/c13-6-4-7(11-5-6)9(14)12-3-1-2-8(12)10(15)16/h6-8,11,13H,1-5H2,(H,15,16)

> <INCHI_KEY>
GIOMWAZJQDYWEU-UHFFFAOYSA-N

> <FORMULA>
C10H16N2O4

> <MOLECULAR_WEIGHT>
228.245

> <EXACT_MASS>
228.11100701

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
22.08807195105728

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(4-hydroxypyrrolidine-2-carbonyl)pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-2.99

> <JCHEM_LOGP>
-3.981392719715238

> <ALOGPS_LOGS>
-0.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.826189272995407

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5399558382577627

> <JCHEM_PKA_STRONGEST_BASIC>
9.140451260189643

> <JCHEM_POLAR_SURFACE_AREA>
89.87

> <JCHEM_REFRACTIVITY>
54.3687

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(4-hydroxypyrrolidine-2-carbonyl)pyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0028871
     RDKit          3D
Hydroxyprolyl-Proline
 32 33  0  0  0  0  0  0  0  0999 V2000
   -0.9405    2.4080    0.1278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0039    2.0219   -0.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0053    2.9147   -0.6925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1650    0.6039   -0.7473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3484   -0.0312   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8388   -1.4391    0.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3990   -1.1360    0.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0154   -0.1960   -0.3873 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2730   -0.0722   -0.9580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5162    0.7897   -1.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4178   -0.9314   -0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7591   -0.7655    0.9233 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8130    0.3086    0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7206    0.1613    1.9522 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4639    0.1649   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6113   -0.6294   -1.2699 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9438    3.9127   -0.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3780    0.5359   -1.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2583   -0.0215   -0.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5178    0.4161    0.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7426   -1.9969   -0.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3959   -1.9927    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5032   -0.5833    1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7826   -2.0300    0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0985   -1.9813   -0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8823   -0.4607    1.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1978   -1.7199    1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2861    1.2924    0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0075    1.0878    2.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385    1.1586   -0.9513 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4920   -0.2846   -0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0609   -1.5050   -1.6321 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
 13 15  1  0
 15 16  1  0
  8  4  1  0
 16 11  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
M  END

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  O   UNK     0       1.367  -0.438   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.033  -1.208   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.300  -0.438   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.033  -2.748   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.279  -3.654   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.803  -5.118   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.737  -5.118   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -1.212  -3.654   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -2.677  -3.178   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.997  -1.671   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.821  -4.208   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -3.661  -5.740   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -5.067  -6.366   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.098  -5.222   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -7.629  -5.383   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.328  -3.888   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    4    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   11                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0028871
HETATM    1  O1  UNL     1      -0.940   2.408   0.128  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.004   2.022  -0.414  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.005   2.915  -0.692  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.165   0.604  -0.747  1.00  0.00           C  
HETATM    5  C3  UNL     1      -3.348  -0.031  -0.033  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.839  -1.439   0.198  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.399  -1.136   0.641  1.00  0.00           C  
HETATM    8  N1  UNL     1      -1.015  -0.196  -0.387  1.00  0.00           N  
HETATM    9  C6  UNL     1       0.273  -0.072  -0.958  1.00  0.00           C  
HETATM   10  O3  UNL     1       0.516   0.790  -1.863  1.00  0.00           O  
HETATM   11  C7  UNL     1       1.418  -0.931  -0.544  1.00  0.00           C  
HETATM   12  C8  UNL     1       1.759  -0.765   0.923  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.813   0.309   0.894  1.00  0.00           C  
HETATM   14  O4  UNL     1       3.721   0.161   1.952  1.00  0.00           O  
HETATM   15  C10 UNL     1       3.464   0.165  -0.443  1.00  0.00           C  
HETATM   16  N2  UNL     1       2.611  -0.629  -1.270  1.00  0.00           N  
HETATM   17  H1  UNL     1      -2.944   3.913  -0.588  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.378   0.536  -1.838  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.258  -0.022  -0.665  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.518   0.416   0.970  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.743  -1.997  -0.761  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.396  -1.993   0.952  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.503  -0.583   1.597  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.783  -2.030   0.692  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.098  -1.981  -0.699  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.882  -0.461   1.506  1.00  0.00           H  
HETATM   27  H11 UNL     1       2.198  -1.720   1.269  1.00  0.00           H  
HETATM   28  H12 UNL     1       2.286   1.292   0.957  1.00  0.00           H  
HETATM   29  H13 UNL     1       4.008   1.088   2.182  1.00  0.00           H  
HETATM   30  H14 UNL     1       3.639   1.159  -0.951  1.00  0.00           H  
HETATM   31  H15 UNL     1       4.492  -0.285  -0.375  1.00  0.00           H  
HETATM   32  H16 UNL     1       3.061  -1.505  -1.632  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   17
CONECT    4    5    8   18
CONECT    5    6   19   20
CONECT    6    7   21   22
CONECT    7    8   23   24
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   16   25
CONECT   12   13   26   27
CONECT   13   14   15   28
CONECT   14   29
CONECT   15   16   30   31
CONECT   16   32
END

HMDB0028871
     RDKit          3D
Hydroxyprolyl-Proline
 32 33  0  0  0  0  0  0  0  0999 V2000
   -0.9405    2.4080    0.1278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0039    2.0219   -0.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0053    2.9147   -0.6925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1650    0.6039   -0.7473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3484   -0.0312   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8388   -1.4391    0.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3990   -1.1360    0.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0154   -0.1960   -0.3873 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2730   -0.0722   -0.9580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5162    0.7897   -1.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4178   -0.9314   -0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7591   -0.7655    0.9233 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8130    0.3086    0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7206    0.1613    1.9522 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4639    0.1649   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6113   -0.6294   -1.2699 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9438    3.9127   -0.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3780    0.5359   -1.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2583   -0.0215   -0.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5178    0.4161    0.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7426   -1.9969   -0.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3959   -1.9927    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5032   -0.5833    1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7826   -2.0300    0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0985   -1.9813   -0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8823   -0.4607    1.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1978   -1.7199    1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2861    1.2924    0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0075    1.0878    2.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385    1.1586   -0.9513 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4920   -0.2846   -0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0609   -1.5050   -1.6321 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
 13 15  1  0
 15 16  1  0
  8  4  1  0
 16 11  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Hydroxyproline proline dipeptide	HMDB
HP-p Dipeptide	HMDB
HPP Dipeptide	HMDB
Hpro-pro	HMDB
Hydroxyproline-proline dipeptide	HMDB
Hydroxyprolylproline	HMDB
L-Hydroxyprolyl-L-proline	HMDB
1-(4-Hydroxypyrrolidine-2-carbonyl)pyrrolidine-2-carboxylate	HMDB

Chemical Formula

C₁₀H₁₆N₂O₄

Average Molecular Weight

228.245

Monoisotopic Molecular Weight

228.11100701

IUPAC Name

1-(4-hydroxypyrrolidine-2-carbonyl)pyrrolidine-2-carboxylic acid

Traditional Name

1-(4-hydroxypyrrolidine-2-carbonyl)pyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC1CNC(C1)C(=O)N1CCCC1C(O)=O

InChI Identifier

InChI=1S/C10H16N2O4/c13-6-4-7(11-5-6)9(14)12-3-1-2-8(12)10(15)16/h6-8,11,13H,1-5H2,(H,15,16)

InChI Key

GIOMWAZJQDYWEU-UHFFFAOYSA-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
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Proline or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine-2-carboxamide
Tertiary carboxylic acid amide
Pyrrolidine
1,2-aminoalcohol
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary alcohol
Secondary amine
Organoheterocyclic compound
Azacycle
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Organic oxygen compound
Organopnictogen compound
Organic oxide
Carbonyl group
Alcohol
Amine
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

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	-3.98	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	103 g/L	ALOGPS
logP	-3	ALOGPS
logP	-4	ChemAxon
logS	-0.35	ALOGPS
pKa (Strongest Acidic)	3.54	ChemAxon
pKa (Strongest Basic)	9.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	89.87 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	54.37 m³·mol⁻¹	ChemAxon
Polarizability	22.09 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
DarkChem	[M+H]+	152.481	31661259
DarkChem	[M-H]-	148.894	31661259
DeepCCS	[M+H]+	152.33	30932474
DeepCCS	[M-H]-	149.405	30932474
DeepCCS	[M-2H]-	185.547	30932474
DeepCCS	[M+Na]+	161.085	30932474
AllCCS	[M+H]+	151.5	32859911
AllCCS	[M+H-H2O]+	147.7	32859911
AllCCS	[M+NH4]+	155.0	32859911
AllCCS	[M+Na]+	156.0	32859911
AllCCS	[M-H]-	151.3	32859911
AllCCS	[M+Na-2H]-	151.3	32859911
AllCCS	[M+HCOO]-	151.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydroxyprolyl-Proline	OC1CNC(C1)C(=O)N1CCCC1C(O)=O	3126.1	Standard polar	33892256
Hydroxyprolyl-Proline	OC1CNC(C1)C(=O)N1CCCC1C(O)=O	2010.5	Standard non polar	33892256
Hydroxyprolyl-Proline	OC1CNC(C1)C(=O)N1CCCC1C(O)=O	2257.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydroxyprolyl-Proline,1TMS,isomer #1	C[Si](C)(C)OC1CNC(C(=O)N2CCCC2C(=O)O)C1	2243.2	Semi standard non polar	33892256
Hydroxyprolyl-Proline,1TMS,isomer #2	C[Si](C)(C)OC(=O)C1CCCN1C(=O)C1CC(O)CN1	2182.7	Semi standard non polar	33892256
Hydroxyprolyl-Proline,1TMS,isomer #3	C[Si](C)(C)N1CC(O)CC1C(=O)N1CCCC1C(=O)O	2113.1	Semi standard non polar	33892256
Hydroxyprolyl-Proline,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1CCCN1C(=O)C1CC(O[Si](C)(C)C)CN1	2202.8	Semi standard non polar	33892256
Hydroxyprolyl-Proline,2TMS,isomer #2	C[Si](C)(C)OC1CC(C(=O)N2CCCC2C(=O)O)N([Si](C)(C)C)C1	2203.4	Semi standard non polar	33892256
Hydroxyprolyl-Proline,2TMS,isomer #3	C[Si](C)(C)OC(=O)C1CCCN1C(=O)C1CC(O)CN1[Si](C)(C)C	2156.7	Semi standard non polar	33892256
Hydroxyprolyl-Proline,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1CCCN1C(=O)C1CC(O[Si](C)(C)C)CN1[Si](C)(C)C	2222.3	Semi standard non polar	33892256
Hydroxyprolyl-Proline,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1CCCN1C(=O)C1CC(O[Si](C)(C)C)CN1[Si](C)(C)C	2230.3	Standard non polar	33892256
Hydroxyprolyl-Proline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CNC(C(=O)N2CCCC2C(=O)O)C1	2474.3	Semi standard non polar	33892256
Hydroxyprolyl-Proline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1CCCN1C(=O)C1CC(O)CN1	2440.8	Semi standard non polar	33892256
Hydroxyprolyl-Proline,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1CC(O)CC1C(=O)N1CCCC1C(=O)O	2399.6	Semi standard non polar	33892256
Hydroxyprolyl-Proline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CCCN1C(=O)C1CC(O[Si](C)(C)C(C)(C)C)CN1	2686.3	Semi standard non polar	33892256
Hydroxyprolyl-Proline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1CC(C(=O)N2CCCC2C(=O)O)N([Si](C)(C)C(C)(C)C)C1	2685.4	Semi standard non polar	33892256
Hydroxyprolyl-Proline,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1CCCN1C(=O)C1CC(O)CN1[Si](C)(C)C(C)(C)C	2632.9	Semi standard non polar	33892256
Hydroxyprolyl-Proline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CCCN1C(=O)C1CC(O[Si](C)(C)C(C)(C)C)CN1[Si](C)(C)C(C)(C)C	2903.6	Semi standard non polar	33892256
Hydroxyprolyl-Proline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CCCN1C(=O)C1CC(O[Si](C)(C)C(C)(C)C)CN1[Si](C)(C)C(C)(C)C	2849.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyprolyl-Proline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-653c7ef64f80843a5e62	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyprolyl-Proline GC-MS (2 TMS) - 70eV, Positive	splash10-002f-9533000000-5194c44ce90be529ae0a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyprolyl-Proline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyprolyl-Proline 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 - Hydroxyprolyl-Proline 10V, Positive-QTOF	splash10-03di-0290000000-c95f0b426e4881c831ab	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyprolyl-Proline 20V, Positive-QTOF	splash10-014i-9330000000-61c203facbdc52d95969	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyprolyl-Proline 40V, Positive-QTOF	splash10-014i-9100000000-262fe75accba1bc4dad0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyprolyl-Proline 10V, Negative-QTOF	splash10-0059-0590000000-1b06eb0c3f1b4579d884	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyprolyl-Proline 20V, Negative-QTOF	splash10-07w9-2930000000-d72e33090bad68b675aa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyprolyl-Proline 40V, Negative-QTOF	splash10-044i-9400000000-d97b0f25f7d16df2e510	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyprolyl-Proline 10V, Positive-QTOF	splash10-004i-0190000000-bc37f3f9c2a9681d9c31	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyprolyl-Proline 20V, Positive-QTOF	splash10-02i2-9550000000-e6426ff0a0091d096e27	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyprolyl-Proline 40V, Positive-QTOF	splash10-00xr-9400000000-eecfb81b6bf4c9ad2e46	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyprolyl-Proline 10V, Negative-QTOF	splash10-01t9-0790000000-6c73e0db43c421fc5825	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyprolyl-Proline 20V, Negative-QTOF	splash10-03di-4910000000-3f29ee800f0cbd977815	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyprolyl-Proline 40V, Negative-QTOF	splash10-03dj-9700000000-38aabc322e383e4c4bf4	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

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

FDB111900

KNApSAcK ID

Not Available

Chemspider ID

35032807

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61156945

PDB ID

Not Available

ChEBI ID

169724

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Hydroxyprolyl-Proline (HMDB0028871)

MOL for HMDB0028871 (Hydroxyprolyl-Proline)

3D MOL for HMDB0028871 (Hydroxyprolyl-Proline)

3D SDF for HMDB0028871 (Hydroxyprolyl-Proline)

3D-SDF for HMDB0028871 (Hydroxyprolyl-Proline)

PDB for HMDB0028871 (Hydroxyprolyl-Proline)

3D PDB for HMDB0028871 (Hydroxyprolyl-Proline)

SMILES for HMDB0028871 (Hydroxyprolyl-Proline)

INCHI for HMDB0028871 (Hydroxyprolyl-Proline)

Structure for HMDB0028871 (Hydroxyprolyl-Proline)

3D Structure for HMDB0028871 (Hydroxyprolyl-Proline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra