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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 21:03:43 UTC

Update Date

2021-09-14 15:37:04 UTC

HMDB ID

HMDB0029106

Secondary Accession Numbers

HMDB29106

Metabolite Identification

Common Name

Tyrosylhydroxyproline

Description

Tyrosylhydroxyproline, also known as y-HP dipeptide or tyr-hpro, 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. Tyrosylhydroxyproline has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make tyrosylhydroxyproline a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Tyrosylhydroxyproline.

Structure

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

HMDB0029106
     RDKit          3D
Tyrosylhydroxyproline
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.0855   -1.4272   -1.9122 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2183   -2.1905   -0.7370 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7174   -2.1833   -0.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2692   -0.8232   -0.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7434   -0.0771   -1.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2624    1.1897   -1.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237    1.7596   -0.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8333    3.0374    0.1934 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595    1.0358    1.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3378   -0.2347    0.9095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5425   -1.6755    0.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851   -2.2874    1.5206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4785   -0.6346    0.4435 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1487   -0.2379    1.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3630    0.5186    1.2956 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4850   -0.0821    1.8613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4044    0.5551   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9778    0.2095   -0.6062 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2288    1.5115   -0.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5271    2.3724   -1.5309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2010    1.7597    0.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3913   -0.5183   -1.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2598   -1.9274   -2.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0788   -3.2669   -0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1881   -2.6249   -1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9954   -2.7848    0.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7057   -0.5209   -2.4205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6171    1.7289   -2.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1622    3.8011    0.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8924    1.4605    2.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9785   -0.7883    1.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4101   -1.1600    2.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031    0.3858    2.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3437    1.5642    1.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4274   -1.0829    1.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6953    1.5586   -0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0821   -0.2119   -0.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0220   -0.2368   -1.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344    2.5284    0.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 10  4  1  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  6
  3 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  1
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  6
 21 39  1  0
M  END


  Mrv1652304062014222D          

 21 22  0  0  0  0            999 V2000
10002.1009 9999.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8128 9999.2054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.100910000.4412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8095 9997.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7175 9999.7002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.0502 9999.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3051 9998.4306    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.1301 9998.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3850 9999.2152    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.717510000.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.432010000.9377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.574110000.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.288610000.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.003110001.7627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.003110000.9377    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.574110001.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.859610002.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.145110001.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.145110000.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.859610000.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.430710002.1753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  7  4  1  1  0  0  0
  9  1  1  6  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  6  0  0  0
 10 15  1  0  0  0  0
 13 12  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 16  2  0  0  0  0
 20 12  1  0  0  0  0
 18 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029106

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CC1=CC=C(O)C=C1)C(=O)N1C[C@H](O)C[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H18N2O5/c15-11(5-8-1-3-9(17)4-2-8)13(19)16-7-10(18)6-12(16)14(20)21/h1-4,10-12,17-18H,5-7,15H2,(H,20,21)/t10-,11+,12+/m1/s1

> <INCHI_KEY>
FTWOPDCJCRFTHX-WOPDTQHZSA-N

> <FORMULA>
C14H18N2O5

> <MOLECULAR_WEIGHT>
294.307

> <EXACT_MASS>
294.121571688

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.774847828807754

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4R)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]-4-hydroxypyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-2.21

> <JCHEM_LOGP>
-2.903000781492928

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.518397281336616

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4349802461149346

> <JCHEM_PKA_STRONGEST_BASIC>
8.013711746235789

> <JCHEM_POLAR_SURFACE_AREA>
124.09

> <JCHEM_REFRACTIVITY>
73.40160000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.84e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4R)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]-4-hydroxypyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029106
     RDKit          3D
Tyrosylhydroxyproline
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.0855   -1.4272   -1.9122 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2183   -2.1905   -0.7370 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7174   -2.1833   -0.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2692   -0.8232   -0.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7434   -0.0771   -1.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2624    1.1897   -1.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237    1.7596   -0.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8333    3.0374    0.1934 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595    1.0358    1.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3378   -0.2347    0.9095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5425   -1.6755    0.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851   -2.2874    1.5206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4785   -0.6346    0.4435 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1487   -0.2379    1.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3630    0.5186    1.2956 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4850   -0.0821    1.8613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4044    0.5551   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9778    0.2095   -0.6062 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2288    1.5115   -0.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5271    2.3724   -1.5309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2010    1.7597    0.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3913   -0.5183   -1.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2598   -1.9274   -2.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0788   -3.2669   -0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1881   -2.6249   -1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9954   -2.7848    0.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7057   -0.5209   -2.4205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6171    1.7289   -2.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1622    3.8011    0.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8924    1.4605    2.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9785   -0.7883    1.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4101   -1.1600    2.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031    0.3858    2.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3437    1.5642    1.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4274   -1.0829    1.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6953    1.5586   -0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0821   -0.2119   -0.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0220   -0.2368   -1.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344    2.5284    0.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 10  4  1  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  6
  3 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  1
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  6
 21 39  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  C   UNK     0    8670.5888665.953   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8671.9178665.183   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8670.5888667.490   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8666.3118662.504   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0    8668.0068666.107   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8666.7608665.202   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8667.2368663.737   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8668.7768663.737   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8669.2528665.202   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8668.0068667.647   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8669.3408668.417   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8664.0058668.417   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.3398667.647   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0    8666.6728669.957   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0    8666.6728668.417   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.0058669.957   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8662.6718670.727   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8661.3388669.957   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8661.3388668.417   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8662.6718667.647   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8660.0048670.727   0.000  0.00  0.00           O+0
CONECT    1    2    3    9                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    7                                                            
CONECT    5    6    9   10                                                  
CONECT    6    7    5                                                       
CONECT    7    6    8    4                                                  
CONECT    8    7    9                                                       
CONECT    9    8    5    1                                                  
CONECT   10    5   11   15                                                  
CONECT   11   10                                                            
CONECT   12   13   16   20                                                  
CONECT   13   15   12                                                       
CONECT   14   15                                                            
CONECT   15   13   14   10                                                  
CONECT   16   17   12                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19   12                                                       
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0029106
HETATM    1  N1  UNL     1      -0.086  -1.427  -1.912  1.00  0.00           N  
HETATM    2  C1  UNL     1       0.218  -2.191  -0.737  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.717  -2.183  -0.517  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.269  -0.823  -0.338  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.743  -0.077  -1.415  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.262   1.190  -1.280  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.324   1.760  -0.038  1.00  0.00           C  
HETATM    8  O1  UNL     1       3.833   3.037   0.193  1.00  0.00           O  
HETATM    9  C7  UNL     1       2.859   1.036   1.037  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.338  -0.235   0.910  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.543  -1.675   0.417  1.00  0.00           C  
HETATM   12  O2  UNL     1      -0.285  -2.287   1.521  1.00  0.00           O  
HETATM   13  N2  UNL     1      -1.479  -0.635   0.444  1.00  0.00           N  
HETATM   14  C10 UNL     1      -2.149  -0.238   1.704  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.363   0.519   1.296  1.00  0.00           C  
HETATM   16  O3  UNL     1      -4.485  -0.082   1.861  1.00  0.00           O  
HETATM   17  C12 UNL     1      -3.404   0.555  -0.192  1.00  0.00           C  
HETATM   18  C13 UNL     1      -1.978   0.210  -0.606  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.229   1.512  -0.673  1.00  0.00           C  
HETATM   20  O4  UNL     1      -1.527   2.372  -1.531  1.00  0.00           O  
HETATM   21  O5  UNL     1      -0.201   1.760   0.223  1.00  0.00           O  
HETATM   22  H1  UNL     1       0.391  -0.518  -1.872  1.00  0.00           H  
HETATM   23  H2  UNL     1       0.260  -1.927  -2.774  1.00  0.00           H  
HETATM   24  H3  UNL     1      -0.079  -3.267  -0.907  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.188  -2.625  -1.404  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.995  -2.785   0.383  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.706  -0.521  -2.421  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.617   1.729  -2.141  1.00  0.00           H  
HETATM   29  H8  UNL     1       3.162   3.801   0.146  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.892   1.461   2.051  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.978  -0.788   1.780  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.410  -1.160   2.224  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.403   0.386   2.250  1.00  0.00           H  
HETATM   34  H13 UNL     1      -3.344   1.564   1.693  1.00  0.00           H  
HETATM   35  H14 UNL     1      -4.427  -1.083   1.815  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.695   1.559  -0.534  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.082  -0.212  -0.582  1.00  0.00           H  
HETATM   38  H17 UNL     1      -2.022  -0.237  -1.604  1.00  0.00           H  
HETATM   39  H18 UNL     1       0.434   2.528   0.057  1.00  0.00           H  
CONECT    1    2   22   23
CONECT    2    3   11   24
CONECT    3    4   25   26
CONECT    4    5    5   10
CONECT    5    6   27
CONECT    6    7    7   28
CONECT    7    8    9
CONECT    8   29
CONECT    9   10   10   30
CONECT   10   31
CONECT   11   12   12   13
CONECT   13   14   18
CONECT   14   15   32   33
CONECT   15   16   17   34
CONECT   16   35
CONECT   17   18   36   37
CONECT   18   19   38
CONECT   19   20   20   21
CONECT   21   39
END

HMDB0029106
     RDKit          3D
Tyrosylhydroxyproline
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.0855   -1.4272   -1.9122 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2183   -2.1905   -0.7370 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7174   -2.1833   -0.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2692   -0.8232   -0.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7434   -0.0771   -1.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2624    1.1897   -1.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237    1.7596   -0.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8333    3.0374    0.1934 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595    1.0358    1.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3378   -0.2347    0.9095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5425   -1.6755    0.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851   -2.2874    1.5206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4785   -0.6346    0.4435 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1487   -0.2379    1.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3630    0.5186    1.2956 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4850   -0.0821    1.8613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4044    0.5551   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9778    0.2095   -0.6062 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2288    1.5115   -0.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5271    2.3724   -1.5309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2010    1.7597    0.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3913   -0.5183   -1.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2598   -1.9274   -2.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0788   -3.2669   -0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1881   -2.6249   -1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9954   -2.7848    0.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7057   -0.5209   -2.4205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6171    1.7289   -2.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1622    3.8011    0.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8924    1.4605    2.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9785   -0.7883    1.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4101   -1.1600    2.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031    0.3858    2.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3437    1.5642    1.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4274   -1.0829    1.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6953    1.5586   -0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0821   -0.2119   -0.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0220   -0.2368   -1.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344    2.5284    0.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 10  4  1  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  6
  3 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  1
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  6
 21 39  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Tyrosine hydroxyproline dipeptide	HMDB
L-Tyrosyl-L-hydroxyproline	HMDB
Tyr-hpro	HMDB
Tyrosine-hydroxyproline dipeptide	HMDB
Y-HP dipeptide	HMDB
YHP dipeptide	HMDB
Tyr-hyp	HMDB
L-Tyr-L-hyp	HMDB
Tyrosyl-hydroxyproline	HMDB
(2S,4R)-1-[(2S)-2-Amino-3-(4-hydroxyphenyl)propanoyl]-4-hydroxypyrrolidine-2-carboxylate	HMDB
Tyrosylhydroxyproline	HMDB

Chemical Formula

C₁₄H₁₈N₂O₅

Average Molecular Weight

294.307

Monoisotopic Molecular Weight

294.121571688

IUPAC Name

(2S,4R)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]-4-hydroxypyrrolidine-2-carboxylic acid

Traditional Name

(2S,4R)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]-4-hydroxypyrrolidine-2-carboxylic acid

CAS Registry Number

936346-34-8

SMILES

N[C@@H](CC1=CC=C(O)C=C1)C(=O)N1C[C@H](O)C[C@H]1C(O)=O

InChI Identifier

InChI=1S/C14H18N2O5/c15-11(5-8-1-3-9(17)4-2-8)13(19)16-7-10(18)6-12(16)14(20)21/h1-4,10-12,17-18H,5-7,15H2,(H,20,21)/t10-,11+,12+/m1/s1

InChI Key

FTWOPDCJCRFTHX-WOPDTQHZSA-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-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
Amphetamine or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Pyrrolidine
Amino acid or derivatives
Carboxamide group
Secondary alcohol
Amino acid
Azacycle
Carboxylic acid
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic oxygen compound
Primary aliphatic amine
Organic nitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Feces (PMID: 26848182)

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	-2.9	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.84 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-2.9	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	8.01	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.09 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.4 m³·mol⁻¹	ChemAxon
Polarizability	28.77 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]+	170.507	30932474
DeepCCS	[M-H]-	168.149	30932474
DeepCCS	[M-2H]-	202.202	30932474
DeepCCS	[M+Na]+	177.818	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tyrosylhydroxyproline	N[C@@H](CC1=CC=C(O)C=C1)C(=O)N1C[C@H](O)C[C@H]1C(O)=O	4132.6	Standard polar	33892256
Tyrosylhydroxyproline	N[C@@H](CC1=CC=C(O)C=C1)C(=O)N1C[C@H](O)C[C@H]1C(O)=O	2879.8	Standard non polar	33892256
Tyrosylhydroxyproline	N[C@@H](CC1=CC=C(O)C=C1)C(=O)N1C[C@H](O)C[C@H]1C(O)=O	3025.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tyrosylhydroxyproline,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)N2C[C@H](O)C[C@H]2C(=O)O)C=C1	2752.1	Semi standard non polar	33892256
Tyrosylhydroxyproline,1TMS,isomer #2	C[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@@H](N)CC2=CC=C(O)C=C2)C1	2812.2	Semi standard non polar	33892256
Tyrosylhydroxyproline,1TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H](N)CC1=CC=C(O)C=C1	2717.4	Semi standard non polar	33892256
Tyrosylhydroxyproline,1TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CC=C(O)C=C1)C(=O)N1C[C@H](O)C[C@H]1C(=O)O	2802.9	Semi standard non polar	33892256
Tyrosylhydroxyproline,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)N2C[C@H](O[Si](C)(C)C)C[C@H]2C(=O)O)C=C1	2750.1	Semi standard non polar	33892256
Tyrosylhydroxyproline,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H](N)CC1=CC=C(O[Si](C)(C)C)C=C1	2723.9	Semi standard non polar	33892256
Tyrosylhydroxyproline,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)N1C[C@H](O)C[C@H]1C(=O)O	2755.9	Semi standard non polar	33892256
Tyrosylhydroxyproline,2TMS,isomer #4	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@@H](N)CC1=CC=C(O)C=C1	2720.4	Semi standard non polar	33892256
Tyrosylhydroxyproline,2TMS,isomer #5	C[Si](C)(C)N[C@@H](CC1=CC=C(O)C=C1)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O	2765.7	Semi standard non polar	33892256
Tyrosylhydroxyproline,2TMS,isomer #6	C[Si](C)(C)N[C@@H](CC1=CC=C(O)C=C1)C(=O)N1C[C@H](O)C[C@H]1C(=O)O[Si](C)(C)C	2717.4	Semi standard non polar	33892256
Tyrosylhydroxyproline,2TMS,isomer #7	C[Si](C)(C)N([C@@H](CC1=CC=C(O)C=C1)C(=O)N1C[C@H](O)C[C@H]1C(=O)O)[Si](C)(C)C	2897.1	Semi standard non polar	33892256
Tyrosylhydroxyproline,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@@H](N)CC1=CC=C(O[Si](C)(C)C)C=C1	2734.4	Semi standard non polar	33892256
Tyrosylhydroxyproline,3TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O	2746.1	Semi standard non polar	33892256
Tyrosylhydroxyproline,3TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)N1C[C@H](O)C[C@H]1C(=O)O[Si](C)(C)C	2718.6	Semi standard non polar	33892256
Tyrosylhydroxyproline,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)N2C[C@H](O)C[C@H]2C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1	2874.1	Semi standard non polar	33892256
Tyrosylhydroxyproline,3TMS,isomer #5	C[Si](C)(C)N[C@@H](CC1=CC=C(O)C=C1)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C	2691.4	Semi standard non polar	33892256
Tyrosylhydroxyproline,3TMS,isomer #6	C[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@H](CC2=CC=C(O)C=C2)N([Si](C)(C)C)[Si](C)(C)C)C1	2884.5	Semi standard non polar	33892256
Tyrosylhydroxyproline,3TMS,isomer #7	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](CC1=CC=C(O)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2852.4	Semi standard non polar	33892256
Tyrosylhydroxyproline,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C	2735.9	Semi standard non polar	33892256
Tyrosylhydroxyproline,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C	2672.1	Standard non polar	33892256
Tyrosylhydroxyproline,4TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)N2C[C@H](O[Si](C)(C)C)C[C@H]2C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1	2904.9	Semi standard non polar	33892256
Tyrosylhydroxyproline,4TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)N2C[C@H](O[Si](C)(C)C)C[C@H]2C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1	2795.8	Standard non polar	33892256
Tyrosylhydroxyproline,4TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2872.1	Semi standard non polar	33892256
Tyrosylhydroxyproline,4TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2747.8	Standard non polar	33892256
Tyrosylhydroxyproline,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@H](CC1=CC=C(O)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2868.8	Semi standard non polar	33892256
Tyrosylhydroxyproline,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@H](CC1=CC=C(O)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2795.3	Standard non polar	33892256
Tyrosylhydroxyproline,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2917.0	Semi standard non polar	33892256
Tyrosylhydroxyproline,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2765.3	Standard non polar	33892256
Tyrosylhydroxyproline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)N2C[C@H](O)C[C@H]2C(=O)O)C=C1	3025.9	Semi standard non polar	33892256
Tyrosylhydroxyproline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@@H](N)CC2=CC=C(O)C=C2)C1	3065.5	Semi standard non polar	33892256
Tyrosylhydroxyproline,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H](N)CC1=CC=C(O)C=C1	2987.4	Semi standard non polar	33892256
Tyrosylhydroxyproline,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O)C=C1)C(=O)N1C[C@H](O)C[C@H]1C(=O)O	3038.5	Semi standard non polar	33892256
Tyrosylhydroxyproline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)N2C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]2C(=O)O)C=C1	3271.5	Semi standard non polar	33892256
Tyrosylhydroxyproline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H](N)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3211.0	Semi standard non polar	33892256
Tyrosylhydroxyproline,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)N1C[C@H](O)C[C@H]1C(=O)O	3272.2	Semi standard non polar	33892256
Tyrosylhydroxyproline,2TBDMS,isomer #4	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](N)CC1=CC=C(O)C=C1	3223.7	Semi standard non polar	33892256
Tyrosylhydroxyproline,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O)C=C1)C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)O	3265.8	Semi standard non polar	33892256
Tyrosylhydroxyproline,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O)C=C1)C(=O)N1C[C@H](O)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3211.8	Semi standard non polar	33892256
Tyrosylhydroxyproline,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=C(O)C=C1)C(=O)N1C[C@H](O)C[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	3314.0	Semi standard non polar	33892256
Tyrosylhydroxyproline,3TBDMS,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](N)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3439.3	Semi standard non polar	33892256
Tyrosylhydroxyproline,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)O	3501.1	Semi standard non polar	33892256
Tyrosylhydroxyproline,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)N1C[C@H](O)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3449.4	Semi standard non polar	33892256
Tyrosylhydroxyproline,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)N2C[C@H](O)C[C@H]2C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3597.8	Semi standard non polar	33892256
Tyrosylhydroxyproline,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O)C=C1)C(=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	3419.4	Semi standard non polar	33892256
Tyrosylhydroxyproline,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@H](CC2=CC=C(O)C=C2)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1	3568.7	Semi standard non polar	33892256
Tyrosylhydroxyproline,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](CC1=CC=C(O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3526.6	Semi standard non polar	33892256
Tyrosylhydroxyproline,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=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	3675.6	Semi standard non polar	33892256
Tyrosylhydroxyproline,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=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	3405.3	Standard non polar	33892256
Tyrosylhydroxyproline,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)N2C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]2C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3865.5	Semi standard non polar	33892256
Tyrosylhydroxyproline,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)N2C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]2C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3509.4	Standard non polar	33892256
Tyrosylhydroxyproline,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3807.7	Semi standard non polar	33892256
Tyrosylhydroxyproline,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3490.3	Standard non polar	33892256
Tyrosylhydroxyproline,4TBDMS,isomer #4	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](CC1=CC=C(O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3767.8	Semi standard non polar	33892256
Tyrosylhydroxyproline,4TBDMS,isomer #4	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](CC1=CC=C(O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3502.2	Standard non polar	33892256
Tyrosylhydroxyproline,5TBDMS,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](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4049.3	Semi standard non polar	33892256
Tyrosylhydroxyproline,5TBDMS,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](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3597.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tyrosylhydroxyproline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tyrosylhydroxyproline 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 - Tyrosylhydroxyproline 10V, Negative-QTOF	splash10-03fu-0890000000-acf3f0af257ef92640e5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tyrosylhydroxyproline 20V, Negative-QTOF	splash10-03di-1900000000-500625e4aa1a845fc62e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tyrosylhydroxyproline 40V, Negative-QTOF	splash10-052f-9400000000-f10558975205fca7e035	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tyrosylhydroxyproline 10V, Positive-QTOF	splash10-0002-0590000000-0f2fc35703be5ee9fb66	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tyrosylhydroxyproline 20V, Positive-QTOF	splash10-000i-0910000000-d36911046a516fb81b59	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tyrosylhydroxyproline 40V, Positive-QTOF	splash10-06yd-4900000000-073bbd508962183a1cf8	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Iron deficiency	26848182	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	26848182	details

Associated Disorders and Diseases

Disease References

Iron deficiency
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Ulcerative colitis
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112110

KNApSAcK ID

Not Available

Chemspider ID

43627780

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

69040603

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

Not Available

Showing metabocard for Tyrosylhydroxyproline (HMDB0029106)

MOL for HMDB0029106 (Tyrosylhydroxyproline)

3D MOL for HMDB0029106 (Tyrosylhydroxyproline)

3D SDF for HMDB0029106 (Tyrosylhydroxyproline)

3D-SDF for HMDB0029106 (Tyrosylhydroxyproline)

PDB for HMDB0029106 (Tyrosylhydroxyproline)

3D PDB for HMDB0029106 (Tyrosylhydroxyproline)

SMILES for HMDB0029106 (Tyrosylhydroxyproline)

INCHI for HMDB0029106 (Tyrosylhydroxyproline)

Structure for HMDB0029106 (Tyrosylhydroxyproline)

3D Structure for HMDB0029106 (Tyrosylhydroxyproline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra