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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:39 UTC

Update Date

2021-09-14 15:48:25 UTC

HMDB ID

HMDB0002171

Secondary Accession Numbers

HMDB02171

Metabolite Identification

Common Name

Glycylprolylhydroxyproline

Description

Glycylprolylhydroxyproline, also known as gly-pro-hyp, belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Based on a literature review a small amount of articles have been published on Glycylprolylhydroxyproline.

Structure

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

HMDB0002171
     RDKit          3D
Glycylprolylhydroxyproline
 39 40  0  0  0  0  0  0  0  0999 V2000
    4.6336    2.5029   -0.7279 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2180    1.1621   -0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7575    0.9671   -0.6161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0618    1.9584   -0.9364 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1091   -0.2737   -0.4128 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522   -1.4835   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9075   -2.6267   -0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5419   -1.9927   -0.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7098   -0.5730   -0.5253 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1303    0.3385    0.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3980    1.2455    0.9776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5432    0.2195    0.3236 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3248   -0.7692   -0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6763   -0.1188   -0.6466 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9157    0.0588   -2.0079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5908    1.2253    0.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4944    1.0097    1.0515 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9937    0.3467    2.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5982   -0.7908    2.5912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9195    1.0287    3.0436 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0055    2.9434   -1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6287    2.4756   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7673    0.4556   -1.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4565    0.8925    0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6916   -1.5510   -0.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2213   -1.3120    1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094   -3.0978   -1.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0651   -3.3864    0.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1649   -2.5422   -0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1252   -2.0300    0.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4160   -0.5242   -1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8621   -0.9832   -1.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4146   -1.6655    0.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4661   -0.7065   -0.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0775    0.4167   -2.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2952    2.0116   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5589    1.5067    0.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0077    1.9886    1.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5424    1.6735    3.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  9  5  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  6
 13 32  1  0
 13 33  1  0
 14 34  1  1
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  1
 20 39  1  0
M  END


  Mrv1652307191923402D          

 20 21  0  0  0  0            999 V2000
10000.400510000.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.113510001.1676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7647 9999.8386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.4798 9999.4255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.764710000.6627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.4711 9997.9877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.3821 9999.9199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7147 9999.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9696 9998.6503    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7946 9998.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0495 9999.4349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.685810001.1676    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.599510001.9881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.792610002.1597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.380110001.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.932110000.8321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.212610002.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.041010003.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.997210002.2853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.256410003.6020    0.0000 N   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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  1  7  1  0  0  0  0
 11  3  1  6  0  0  0
  9  6  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 13 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12  1  1  6  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  1  0  0  0  0
 17 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002171

> <DATABASE_NAME>
hmdb

> <SMILES>
NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H19N3O5/c13-5-10(17)14-3-1-2-8(14)11(18)15-6-7(16)4-9(15)12(19)20/h7-9,16H,1-6,13H2,(H,19,20)/t7-,8+,9+/m1/s1

> <INCHI_KEY>
SZEOBSAZWJLOGY-VGMNWLOBSA-N

> <FORMULA>
C12H19N3O5

> <MOLECULAR_WEIGHT>
285.3

> <EXACT_MASS>
285.132470724

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.281824968298977

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4R)-1-[(2S)-1-(2-aminoacetyl)pyrrolidine-2-carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-2.79

> <JCHEM_LOGP>
-5.089113307858715

> <ALOGPS_LOGS>
-0.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.826412141486205

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.466849300932415

> <JCHEM_PKA_STRONGEST_BASIC>
7.831451112124936

> <JCHEM_POLAR_SURFACE_AREA>
124.16999999999997

> <JCHEM_REFRACTIVITY>
67.2943

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.76e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4R)-1-[(2S)-1-(2-aminoacetyl)pyrrolidine-2-carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002171
     RDKit          3D
Glycylprolylhydroxyproline
 39 40  0  0  0  0  0  0  0  0999 V2000
    4.6336    2.5029   -0.7279 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2180    1.1621   -0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7575    0.9671   -0.6161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0618    1.9584   -0.9364 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1091   -0.2737   -0.4128 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522   -1.4835   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9075   -2.6267   -0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5419   -1.9927   -0.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7098   -0.5730   -0.5253 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1303    0.3385    0.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3980    1.2455    0.9776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5432    0.2195    0.3236 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3248   -0.7692   -0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6763   -0.1188   -0.6466 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9157    0.0588   -2.0079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5908    1.2253    0.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4944    1.0097    1.0515 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9937    0.3467    2.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5982   -0.7908    2.5912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9195    1.0287    3.0436 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0055    2.9434   -1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6287    2.4756   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7673    0.4556   -1.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4565    0.8925    0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6916   -1.5510   -0.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2213   -1.3120    1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094   -3.0978   -1.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0651   -3.3864    0.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1649   -2.5422   -0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1252   -2.0300    0.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4160   -0.5242   -1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8621   -0.9832   -1.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4146   -1.6655    0.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4661   -0.7065   -0.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0775    0.4167   -2.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2952    2.0116   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5589    1.5067    0.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0077    1.9886    1.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5424    1.6735    3.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  9  5  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  6
 13 32  1  0
 13 33  1  0
 14 34  1  1
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  1
 20 39  1  0
M  END

HEADER    PROTEIN                                 19-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUL-19         0                                  
HETATM    1  C   UNK     0    8667.4148668.077   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8668.7458668.846   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8669.9618666.365   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8671.2968665.594   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8669.9618667.904   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8665.6798662.910   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0    8667.3808666.517   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0    8666.1348665.612   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8666.6108664.147   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8668.1508664.147   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8668.6268665.612   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8666.0808668.846   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0    8665.9198670.378   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0    8664.4138670.698   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.6438669.364   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.6738668.220   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8667.0648671.408   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8666.7438672.915   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8668.5288670.933   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0    8665.2798673.390   0.000  0.00  0.00           N+0
CONECT    1    2    7   12                                                  
CONECT    2    1                                                            
CONECT    3    4    5   11                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    9                                                            
CONECT    7    8   11    1                                                  
CONECT    8    9    7                                                       
CONECT    9    8   10    6                                                  
CONECT   10    9   11                                                       
CONECT   11   10    7    3                                                  
CONECT   12   16   13    1                                                  
CONECT   13   14   12   17                                                  
CONECT   14   15   13                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17   13   18   19                                                  
CONECT   18   17   20                                                       
CONECT   19   17                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0002171
HETATM    1  N1  UNL     1       4.634   2.503  -0.728  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.218   1.162  -0.471  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.758   0.967  -0.616  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.062   1.958  -0.936  1.00  0.00           O  
HETATM    5  N2  UNL     1       2.109  -0.274  -0.413  1.00  0.00           N  
HETATM    6  C3  UNL     1       2.852  -1.483  -0.036  1.00  0.00           C  
HETATM    7  C4  UNL     1       1.908  -2.627  -0.149  1.00  0.00           C  
HETATM    8  C5  UNL     1       0.542  -1.993  -0.081  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.710  -0.573  -0.525  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.130   0.338   0.291  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.398   1.246   0.978  1.00  0.00           O  
HETATM   12  N3  UNL     1      -1.543   0.219   0.324  1.00  0.00           N  
HETATM   13  C8  UNL     1      -2.325  -0.769  -0.406  1.00  0.00           C  
HETATM   14  C9  UNL     1      -3.676  -0.119  -0.647  1.00  0.00           C  
HETATM   15  O3  UNL     1      -3.916   0.059  -2.008  1.00  0.00           O  
HETATM   16  C10 UNL     1      -3.591   1.225   0.044  1.00  0.00           C  
HETATM   17  C11 UNL     1      -2.494   1.010   1.051  1.00  0.00           C  
HETATM   18  C12 UNL     1      -2.994   0.347   2.268  1.00  0.00           C  
HETATM   19  O4  UNL     1      -2.598  -0.791   2.591  1.00  0.00           O  
HETATM   20  O5  UNL     1      -3.919   1.029   3.044  1.00  0.00           O  
HETATM   21  H1  UNL     1       4.005   2.943  -1.420  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.629   2.476  -1.067  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.767   0.456  -1.146  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.456   0.893   0.600  1.00  0.00           H  
HETATM   25  H5  UNL     1       3.692  -1.551  -0.772  1.00  0.00           H  
HETATM   26  H6  UNL     1       3.221  -1.312   1.002  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.009  -3.098  -1.145  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.065  -3.386   0.644  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.165  -2.542  -0.738  1.00  0.00           H  
HETATM   30  H10 UNL     1       0.125  -2.030   0.944  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.416  -0.524  -1.595  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.862  -0.983  -1.408  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.415  -1.665   0.211  1.00  0.00           H  
HETATM   34  H14 UNL     1      -4.466  -0.707  -0.174  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.077   0.417  -2.392  1.00  0.00           H  
HETATM   36  H16 UNL     1      -3.295   2.012  -0.665  1.00  0.00           H  
HETATM   37  H17 UNL     1      -4.559   1.507   0.501  1.00  0.00           H  
HETATM   38  H18 UNL     1      -2.008   1.989   1.306  1.00  0.00           H  
HETATM   39  H19 UNL     1      -3.542   1.673   3.742  1.00  0.00           H  
CONECT    1    2   21   22
CONECT    2    3   23   24
CONECT    3    4    4    5
CONECT    5    6    9
CONECT    6    7   25   26
CONECT    7    8   27   28
CONECT    8    9   29   30
CONECT    9   10   31
CONECT   10   11   11   12
CONECT   12   13   17
CONECT   13   14   32   33
CONECT   14   15   16   34
CONECT   15   35
CONECT   16   17   36   37
CONECT   17   18   38
CONECT   18   19   19   20
CONECT   20   39
END

HMDB0002171
     RDKit          3D
Glycylprolylhydroxyproline
 39 40  0  0  0  0  0  0  0  0999 V2000
    4.6336    2.5029   -0.7279 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2180    1.1621   -0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7575    0.9671   -0.6161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0618    1.9584   -0.9364 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1091   -0.2737   -0.4128 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522   -1.4835   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9075   -2.6267   -0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5419   -1.9927   -0.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7098   -0.5730   -0.5253 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1303    0.3385    0.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3980    1.2455    0.9776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5432    0.2195    0.3236 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3248   -0.7692   -0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6763   -0.1188   -0.6466 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9157    0.0588   -2.0079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5908    1.2253    0.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4944    1.0097    1.0515 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9937    0.3467    2.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5982   -0.7908    2.5912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9195    1.0287    3.0436 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0055    2.9434   -1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6287    2.4756   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7673    0.4556   -1.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4565    0.8925    0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6916   -1.5510   -0.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2213   -1.3120    1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094   -3.0978   -1.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0651   -3.3864    0.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1649   -2.5422   -0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1252   -2.0300    0.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4160   -0.5242   -1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8621   -0.9832   -1.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4146   -1.6655    0.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4661   -0.7065   -0.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0775    0.4167   -2.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2952    2.0116   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5589    1.5067    0.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0077    1.9886    1.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5424    1.6735    3.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  9  5  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  6
 13 32  1  0
 13 33  1  0
 14 34  1  1
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  1
 20 39  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Gly-pro-hyp	HMDB
Glycyl-prolyl-hydroxyproline	HMDB
Gly-L-pro-L-hyp	HMDB
Glycylprolylhydroxyproline	HMDB

Chemical Formula

C₁₂H₁₉N₃O₅

Average Molecular Weight

285.3

Monoisotopic Molecular Weight

285.132470724

IUPAC Name

(2S,4R)-1-[(2S)-1-(2-aminoacetyl)pyrrolidine-2-carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid

Traditional Name

(2S,4R)-1-[(2S)-1-(2-aminoacetyl)pyrrolidine-2-carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid

CAS Registry Number

2239-67-0

SMILES

NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(O)=O

InChI Identifier

InChI=1S/C12H19N3O5/c13-5-10(17)14-3-1-2-8(14)11(18)15-6-7(16)4-9(15)12(19)20/h7-9,16H,1-6,13H2,(H,19,20)/t7-,8+,9+/m1/s1

InChI Key

SZEOBSAZWJLOGY-VGMNWLOBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0002171)

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)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

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)

Equine

Horse (FooDB: FOOD00378)

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	89.4 g/L	ALOGPS
logP	-2.8	ALOGPS
logP	-5.1	ChemAxon
logS	-0.63	ALOGPS
pKa (Strongest Acidic)	3.47	ChemAxon
pKa (Strongest Basic)	7.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	124.17 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	67.29 m³·mol⁻¹	ChemAxon
Polarizability	27.28 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]+	167.769	30932474
DeepCCS	[M-H]-	165.411	30932474
DeepCCS	[M-2H]-	198.569	30932474
DeepCCS	[M+Na]+	173.862	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.58 minutes	32390414
Predicted by Siyang on May 30, 2022	9.0539 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.94 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	383.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	430.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	228.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	69.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	48.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	260.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	267.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	893.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	548.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	47.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	725.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	189.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	221.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	679.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	617.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	361.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glycylprolylhydroxyproline	NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(O)=O	3310.0	Standard polar	33892256
Glycylprolylhydroxyproline	NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(O)=O	2758.9	Standard non polar	33892256
Glycylprolylhydroxyproline	NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(O)=O	2782.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glycylprolylhydroxyproline,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@@H]2CCCN2C(=O)CN)C1	2494.6	Semi standard non polar	33892256
Glycylprolylhydroxyproline,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H]1CCCN1C(=O)CN	2446.4	Semi standard non polar	33892256
Glycylprolylhydroxyproline,1TMS,isomer #3	C[Si](C)(C)NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(=O)O	2527.4	Semi standard non polar	33892256
Glycylprolylhydroxyproline,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@@H]1CCCN1C(=O)CN	2504.8	Semi standard non polar	33892256
Glycylprolylhydroxyproline,2TMS,isomer #2	C[Si](C)(C)NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O	2544.8	Semi standard non polar	33892256
Glycylprolylhydroxyproline,2TMS,isomer #3	C[Si](C)(C)NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(=O)O[Si](C)(C)C	2522.9	Semi standard non polar	33892256
Glycylprolylhydroxyproline,2TMS,isomer #4	C[Si](C)(C)N(CC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(=O)O)[Si](C)(C)C	2674.4	Semi standard non polar	33892256
Glycylprolylhydroxyproline,3TMS,isomer #1	C[Si](C)(C)NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C	2585.1	Semi standard non polar	33892256
Glycylprolylhydroxyproline,3TMS,isomer #1	C[Si](C)(C)NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C	2651.4	Standard non polar	33892256
Glycylprolylhydroxyproline,3TMS,isomer #1	C[Si](C)(C)NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C	3481.0	Standard polar	33892256
Glycylprolylhydroxyproline,3TMS,isomer #2	C[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@@H]2CCCN2C(=O)CN([Si](C)(C)C)[Si](C)(C)C)C1	2692.3	Semi standard non polar	33892256
Glycylprolylhydroxyproline,3TMS,isomer #2	C[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@@H]2CCCN2C(=O)CN([Si](C)(C)C)[Si](C)(C)C)C1	2773.7	Standard non polar	33892256
Glycylprolylhydroxyproline,3TMS,isomer #2	C[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@@H]2CCCN2C(=O)CN([Si](C)(C)C)[Si](C)(C)C)C1	3615.3	Standard polar	33892256
Glycylprolylhydroxyproline,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H]1CCCN1C(=O)CN([Si](C)(C)C)[Si](C)(C)C	2690.2	Semi standard non polar	33892256
Glycylprolylhydroxyproline,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H]1CCCN1C(=O)CN([Si](C)(C)C)[Si](C)(C)C	2708.5	Standard non polar	33892256
Glycylprolylhydroxyproline,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H]1CCCN1C(=O)CN([Si](C)(C)C)[Si](C)(C)C	3470.6	Standard polar	33892256
Glycylprolylhydroxyproline,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@@H]1CCCN1C(=O)CN([Si](C)(C)C)[Si](C)(C)C	2745.4	Semi standard non polar	33892256
Glycylprolylhydroxyproline,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@@H]1CCCN1C(=O)CN([Si](C)(C)C)[Si](C)(C)C	2753.9	Standard non polar	33892256
Glycylprolylhydroxyproline,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@@H]1CCCN1C(=O)CN([Si](C)(C)C)[Si](C)(C)C	3205.9	Standard polar	33892256
Glycylprolylhydroxyproline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@@H]2CCCN2C(=O)CN)C1	2723.9	Semi standard non polar	33892256
Glycylprolylhydroxyproline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H]1CCCN1C(=O)CN	2685.6	Semi standard non polar	33892256
Glycylprolylhydroxyproline,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(=O)O	2749.9	Semi standard non polar	33892256
Glycylprolylhydroxyproline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C(C)(C)C)CN1C(=O)[C@@H]1CCCN1C(=O)CN	2952.0	Semi standard non polar	33892256
Glycylprolylhydroxyproline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)O	2972.0	Semi standard non polar	33892256
Glycylprolylhydroxyproline,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2970.1	Semi standard non polar	33892256
Glycylprolylhydroxyproline,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(CC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	3073.8	Semi standard non polar	33892256
Glycylprolylhydroxyproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3231.3	Semi standard non polar	33892256
Glycylprolylhydroxyproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3245.1	Standard non polar	33892256
Glycylprolylhydroxyproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3592.6	Standard polar	33892256
Glycylprolylhydroxyproline,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@@H]2CCCN2C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1	3329.1	Semi standard non polar	33892256
Glycylprolylhydroxyproline,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@@H]2CCCN2C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1	3363.3	Standard non polar	33892256
Glycylprolylhydroxyproline,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@@H]2CCCN2C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1	3674.6	Standard polar	33892256
Glycylprolylhydroxyproline,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H]1CCCN1C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3303.6	Semi standard non polar	33892256
Glycylprolylhydroxyproline,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H]1CCCN1C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3315.9	Standard non polar	33892256
Glycylprolylhydroxyproline,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H]1CCCN1C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3581.9	Standard polar	33892256
Glycylprolylhydroxyproline,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C(C)(C)C)CN1C(=O)[C@@H]1CCCN1C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3583.1	Semi standard non polar	33892256
Glycylprolylhydroxyproline,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C(C)(C)C)CN1C(=O)[C@@H]1CCCN1C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3488.2	Standard non polar	33892256
Glycylprolylhydroxyproline,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C(C)(C)C)CN1C(=O)[C@@H]1CCCN1C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3458.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Glycylprolylhydroxyproline 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 - Glycylprolylhydroxyproline 10V, Positive-QTOF	splash10-000i-0190000000-b5dd73f896f0158e2d51	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylprolylhydroxyproline 20V, Positive-QTOF	splash10-004r-3290000000-3dbb361afe5844f31d3b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylprolylhydroxyproline 40V, Positive-QTOF	splash10-00di-9200000000-b1cd204960da8abec32c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylprolylhydroxyproline 10V, Negative-QTOF	splash10-001i-0190000000-195b95a828073af19795	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylprolylhydroxyproline 20V, Negative-QTOF	splash10-03e9-0910000000-afd3e617d6c25282029e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylprolylhydroxyproline 40V, Negative-QTOF	splash10-0006-9300000000-80acc134f595e7a25b8a	2021-09-23	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

FDB022883

KNApSAcK ID

Not Available

Chemspider ID

9953351

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6524

PubChem Compound

11778669

PDB ID

Not Available

ChEBI ID

Not Available

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

Steiner W, Niederwieser A: Peptide analysis as amino alcohols by gas chromatography-mass spectrometry. Application to hyperoligopeptiduria. Detection of Gly-3Hyp-4Hyp and Gly-Pro-4Hyp-Gly. Clin Chim Acta. 1979 Mar 15;92(3):431-41. [PubMed:436283 ]
SMILEY JD, ZIFF M: URINARY HYDROXYPROLINE EXCRETION AND GROWTH. Physiol Rev. 1964 Jan;44:30-44. [PubMed:14105582 ]
Kibrick AC, Milhorat AT: Glycylprolylhydroxyproline: methods for its quantitative determination in urine and blood serum. Biochem Med. 1970 Sep;4(2):79-88. [PubMed:5134921 ]

Showing metabocard for Glycylprolylhydroxyproline (HMDB0002171)

MOL for HMDB0002171 (Glycylprolylhydroxyproline)

3D MOL for HMDB0002171 (Glycylprolylhydroxyproline)

3D SDF for HMDB0002171 (Glycylprolylhydroxyproline)

3D-SDF for HMDB0002171 (Glycylprolylhydroxyproline)

PDB for HMDB0002171 (Glycylprolylhydroxyproline)

3D PDB for HMDB0002171 (Glycylprolylhydroxyproline)

SMILES for HMDB0002171 (Glycylprolylhydroxyproline)

INCHI for HMDB0002171 (Glycylprolylhydroxyproline)

Structure for HMDB0002171 (Glycylprolylhydroxyproline)

3D Structure for HMDB0002171 (Glycylprolylhydroxyproline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra