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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 21:03:37 UTC

Update Date

2021-09-14 15:37:14 UTC

HMDB ID

HMDB0029084

Secondary Accession Numbers

HMDB29084

Metabolite Identification

Common Name

Tryptophylhydroxyproline

Description

Tryptophylhydroxyproline, also known as W-HP dipeptide or TRP-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. Tryptophylhydroxyproline 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 tryptophylhydroxyproline a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Tryptophylhydroxyproline.

Structure

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

HMDB0029084
     RDKit          3D
Tryptophylhydroxyproline
 42 44  0  0  0  0  0  0  0  0999 V2000
   -0.0616   -2.3176    1.5933 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3912   -1.0685    2.1818 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8676   -0.9402    1.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2897   -0.9614    0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7699   -2.0756   -0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0183   -1.7140   -1.3929 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7281   -0.3978   -1.5809 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8316    0.3985   -2.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4691    1.7187   -2.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0158    2.2254   -1.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9244    1.3961   -0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2776    0.0524   -0.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4178    0.0976    1.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596    1.1537    2.5099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4095    0.0873    0.8198 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526   -1.0483   -0.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5802   -0.5787   -1.1229 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7623    0.0631   -2.0589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3540    0.4965   -0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2912    1.1556    0.4381 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9083    1.8663    1.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7803    1.5389    2.7895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6922    2.9863    1.3308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6201   -2.9051    2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6485   -2.7965    1.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2487   -1.2359    3.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1646    0.0503    2.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4152   -1.6969    2.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9247   -3.0709    0.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3849   -2.3142   -2.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1801    0.0326   -3.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5266    2.4104   -3.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7332    3.2592   -1.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5794    1.7793    0.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1181   -1.9072    0.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6806   -1.4105   -0.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1934   -1.3780   -1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2853    0.4384   -2.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8632    1.2041   -1.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1124   -0.0339    0.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7807    1.8871   -0.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5662    3.5533    0.4825 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 12  4  1  0
 20 15  1  0
 12  7  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  1
  3 27  1  0
  3 28  1  0
  5 29  1  0
  6 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  6
 18 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  6
 23 42  1  0
M  END


  Mrv1652304062014182D          

 23 25  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
 9998.487810001.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.680910001.9297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.268410001.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.820410000.6022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.461310001.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.206410000.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7584 9999.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5655 9999.8175    0.0000 C   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
 18 19  1  0  0  0  0
 12 16  2  0  0  0  0
 12 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 19  2  0  0  0  0
 18 20  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029084

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CC1=CNC2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H19N3O4/c17-12(5-9-7-18-13-4-2-1-3-11(9)13)15(21)19-8-10(20)6-14(19)16(22)23/h1-4,7,10,12,14,18,20H,5-6,8,17H2,(H,22,23)/t10-,12+,14+/m1/s1

> <INCHI_KEY>
XMEUQXQNFRSXLF-OSMZGAPFSA-N

> <FORMULA>
C16H19N3O4

> <MOLECULAR_WEIGHT>
317.345

> <EXACT_MASS>
317.137556104

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.87509307918836

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.28

> <JCHEM_LOGP>
-2.500221613063992

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.806099161171513

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6014954115091773

> <JCHEM_PKA_STRONGEST_BASIC>
7.951982196595935

> <JCHEM_POLAR_SURFACE_AREA>
119.65

> <JCHEM_REFRACTIVITY>
82.50720000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.22e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029084
     RDKit          3D
Tryptophylhydroxyproline
 42 44  0  0  0  0  0  0  0  0999 V2000
   -0.0616   -2.3176    1.5933 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3912   -1.0685    2.1818 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8676   -0.9402    1.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2897   -0.9614    0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7699   -2.0756   -0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0183   -1.7140   -1.3929 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7281   -0.3978   -1.5809 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8316    0.3985   -2.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4691    1.7187   -2.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0158    2.2254   -1.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9244    1.3961   -0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2776    0.0524   -0.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4178    0.0976    1.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596    1.1537    2.5099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4095    0.0873    0.8198 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526   -1.0483   -0.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5802   -0.5787   -1.1229 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7623    0.0631   -2.0589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3540    0.4965   -0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2912    1.1556    0.4381 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9083    1.8663    1.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7803    1.5389    2.7895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6922    2.9863    1.3308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6201   -2.9051    2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6485   -2.7965    1.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2487   -1.2359    3.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1646    0.0503    2.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4152   -1.6969    2.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9247   -3.0709    0.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3849   -2.3142   -2.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1801    0.0326   -3.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5266    2.4104   -3.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7332    3.2592   -1.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5794    1.7793    0.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1181   -1.9072    0.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6806   -1.4105   -0.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1934   -1.3780   -1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2853    0.4384   -2.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8632    1.2041   -1.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1124   -0.0339    0.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7807    1.8871   -0.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5662    3.5533    0.4825 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 12  4  1  0
 20 15  1  0
 12  7  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  1
  3 27  1  0
  3 28  1  0
  5 29  1  0
  6 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  6
 18 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  6
 23 42  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    8663.8448669.948   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0    8662.3388670.269   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0    8661.5688668.935   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8662.5988667.791   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8660.0618668.615   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8659.5858667.150   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8660.6168666.006   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8662.1228666.326   0.000  0.00  0.00           C+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   19                                                  
CONECT   13   15   12                                                       
CONECT   14   15                                                            
CONECT   15   13   14   10                                                  
CONECT   16   12   17                                                       
CONECT   17   16   18                                                       
CONECT   18   19   20   17                                                  
CONECT   19   18   12   23                                                  
CONECT   20   21   18                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   19                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0029084
HETATM    1  N1  UNL     1      -0.062  -2.318   1.593  1.00  0.00           N  
HETATM    2  C1  UNL     1       0.391  -1.068   2.182  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.868  -0.940   1.989  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.290  -0.961   0.573  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.770  -2.076  -0.130  1.00  0.00           C  
HETATM    6  N2  UNL     1       3.018  -1.714  -1.393  1.00  0.00           N  
HETATM    7  C5  UNL     1       2.728  -0.398  -1.581  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.832   0.398  -2.698  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.469   1.719  -2.591  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.016   2.225  -1.395  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.924   1.396  -0.293  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.278   0.052  -0.348  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.418   0.098   1.864  1.00  0.00           C  
HETATM   14  O1  UNL     1      -0.260   1.154   2.510  1.00  0.00           O  
HETATM   15  N3  UNL     1      -1.410   0.087   0.820  1.00  0.00           N  
HETATM   16  C12 UNL     1      -1.653  -1.048  -0.014  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.580  -0.579  -1.123  1.00  0.00           C  
HETATM   18  O2  UNL     1      -1.762   0.063  -2.059  1.00  0.00           O  
HETATM   19  C14 UNL     1      -3.354   0.496  -0.406  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.291   1.156   0.438  1.00  0.00           C  
HETATM   21  C16 UNL     1      -2.908   1.866   1.595  1.00  0.00           C  
HETATM   22  O3  UNL     1      -2.780   1.539   2.790  1.00  0.00           O  
HETATM   23  O4  UNL     1      -3.692   2.986   1.331  1.00  0.00           O  
HETATM   24  H1  UNL     1      -0.620  -2.905   2.227  1.00  0.00           H  
HETATM   25  H2  UNL     1       0.648  -2.797   1.032  1.00  0.00           H  
HETATM   26  H3  UNL     1       0.249  -1.236   3.304  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.165   0.050   2.409  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.415  -1.697   2.599  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.925  -3.071   0.252  1.00  0.00           H  
HETATM   30  H7  UNL     1       3.385  -2.314  -2.172  1.00  0.00           H  
HETATM   31  H8  UNL     1       3.180   0.033  -3.638  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.527   2.410  -3.444  1.00  0.00           H  
HETATM   33  H10 UNL     1       1.733   3.259  -1.313  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.579   1.779   0.671  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.118  -1.907   0.473  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.681  -1.411  -0.463  1.00  0.00           H  
HETATM   37  H14 UNL     1      -3.193  -1.378  -1.542  1.00  0.00           H  
HETATM   38  H15 UNL     1      -2.285   0.438  -2.811  1.00  0.00           H  
HETATM   39  H16 UNL     1      -3.863   1.204  -1.092  1.00  0.00           H  
HETATM   40  H17 UNL     1      -4.112  -0.034   0.244  1.00  0.00           H  
HETATM   41  H18 UNL     1      -1.781   1.887  -0.248  1.00  0.00           H  
HETATM   42  H19 UNL     1      -3.566   3.553   0.482  1.00  0.00           H  
CONECT    1    2   24   25
CONECT    2    3   13   26
CONECT    3    4   27   28
CONECT    4    5    5   12
CONECT    5    6   29
CONECT    6    7   30
CONECT    7    8    8   12
CONECT    8    9   31
CONECT    9   10   10   32
CONECT   10   11   33
CONECT   11   12   12   34
CONECT   13   14   14   15
CONECT   15   16   20
CONECT   16   17   35   36
CONECT   17   18   19   37
CONECT   18   38
CONECT   19   20   39   40
CONECT   20   21   41
CONECT   21   22   22   23
CONECT   23   42
END

HMDB0029084
     RDKit          3D
Tryptophylhydroxyproline
 42 44  0  0  0  0  0  0  0  0999 V2000
   -0.0616   -2.3176    1.5933 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3912   -1.0685    2.1818 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8676   -0.9402    1.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2897   -0.9614    0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7699   -2.0756   -0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0183   -1.7140   -1.3929 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7281   -0.3978   -1.5809 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8316    0.3985   -2.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4691    1.7187   -2.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0158    2.2254   -1.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9244    1.3961   -0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2776    0.0524   -0.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4178    0.0976    1.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596    1.1537    2.5099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4095    0.0873    0.8198 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526   -1.0483   -0.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5802   -0.5787   -1.1229 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7623    0.0631   -2.0589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3540    0.4965   -0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2912    1.1556    0.4381 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9083    1.8663    1.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7803    1.5389    2.7895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6922    2.9863    1.3308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6201   -2.9051    2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6485   -2.7965    1.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2487   -1.2359    3.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1646    0.0503    2.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4152   -1.6969    2.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9247   -3.0709    0.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3849   -2.3142   -2.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1801    0.0326   -3.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5266    2.4104   -3.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7332    3.2592   -1.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5794    1.7793    0.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1181   -1.9072    0.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6806   -1.4105   -0.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1934   -1.3780   -1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2853    0.4384   -2.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8632    1.2041   -1.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1124   -0.0339    0.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7807    1.8871   -0.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5662    3.5533    0.4825 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 12  4  1  0
 20 15  1  0
 12  7  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  1
  3 27  1  0
  3 28  1  0
  5 29  1  0
  6 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  6
 18 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  6
 23 42  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Tryptophan hydroxyproline dipeptide	HMDB
L-Tryptophyl-L-hydroxyproline	HMDB
TRP-HPro	HMDB
Tryptophan-hydroxyproline dipeptide	HMDB
W-HP Dipeptide	HMDB
WHP Dipeptide	HMDB
TRP-Hyp	HMDB
L-TRP-L-Hyp	HMDB
Tryptophyl-hydroxyproline	HMDB
(2S,4R)-1-[(2S)-2-Amino-3-(1H-indol-3-yl)propanoyl]-4-hydroxypyrrolidine-2-carboxylate	HMDB
Tryptophylhydroxyproline	HMDB

Chemical Formula

C₁₆H₁₉N₃O₄

Average Molecular Weight

317.345

Monoisotopic Molecular Weight

317.137556104

IUPAC Name

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

Traditional Name

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

CAS Registry Number

844640-75-1

SMILES

N[C@@H](CC1=CNC2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(O)=O

InChI Identifier

InChI=1S/C16H19N3O4/c17-12(5-9-7-18-13-4-2-1-3-11(9)13)15(21)19-8-10(20)6-14(19)16(22)23/h1-4,7,10,12,14,18,20H,5-6,8,17H2,(H,22,23)/t10-,12+,14+/m1/s1

InChI Key

XMEUQXQNFRSXLF-OSMZGAPFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Proline or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Triptan
Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Aralkylamine
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
Secondary alcohol
Amino acid or derivatives
Carboxamide group
Amino acid
Azacycle
Organoheterocyclic compound
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Alcohol
Organonitrogen compound
Carbonyl group
Organooxygen compound
Amine
Primary amine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	-2.5	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.22 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-2.5	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.6	ChemAxon
pKa (Strongest Basic)	7.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	119.65 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.51 m³·mol⁻¹	ChemAxon
Polarizability	31.88 Å³	ChemAxon
Number of Rings	3	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-2H]-	206.088	30932474
DeepCCS	[M+Na]+	181.317	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tryptophylhydroxyproline	N[C@@H](CC1=CNC2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(O)=O	4155.7	Standard polar	33892256
Tryptophylhydroxyproline	N[C@@H](CC1=CNC2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(O)=O	2993.8	Standard non polar	33892256
Tryptophylhydroxyproline	N[C@@H](CC1=CNC2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(O)=O	3260.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tryptophylhydroxyproline,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@@H](N)CC2=C[NH]C3=CC=CC=C23)C1	3107.1	Semi standard non polar	33892256
Tryptophylhydroxyproline,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H](N)CC1=C[NH]C2=CC=CC=C12	3040.4	Semi standard non polar	33892256
Tryptophylhydroxyproline,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(=O)O	3118.8	Semi standard non polar	33892256
Tryptophylhydroxyproline,1TMS,isomer #4	C[Si](C)(C)N1C=C(C[C@H](N)C(=O)N2C[C@H](O)C[C@H]2C(=O)O)C2=CC=CC=C21	3030.9	Semi standard non polar	33892256
Tryptophylhydroxyproline,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@@H](N)CC1=C[NH]C2=CC=CC=C12	3072.8	Semi standard non polar	33892256
Tryptophylhydroxyproline,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O	3090.5	Semi standard non polar	33892256
Tryptophylhydroxyproline,2TMS,isomer #3	C[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@@H](N)CC2=CN([Si](C)(C)C)C3=CC=CC=C23)C1	3051.1	Semi standard non polar	33892256
Tryptophylhydroxyproline,2TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(=O)O[Si](C)(C)C	3048.1	Semi standard non polar	33892256
Tryptophylhydroxyproline,2TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2984.9	Semi standard non polar	33892256
Tryptophylhydroxyproline,2TMS,isomer #6	C[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(=O)O)[Si](C)(C)C	3190.4	Semi standard non polar	33892256
Tryptophylhydroxyproline,2TMS,isomer #7	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(=O)O	3067.3	Semi standard non polar	33892256
Tryptophylhydroxyproline,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C	3065.0	Semi standard non polar	33892256
Tryptophylhydroxyproline,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C	3064.5	Standard non polar	33892256
Tryptophylhydroxyproline,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	3036.6	Semi standard non polar	33892256
Tryptophylhydroxyproline,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2930.7	Standard non polar	33892256
Tryptophylhydroxyproline,3TMS,isomer #3	C[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@H](CC2=C[NH]C3=CC=CC=C23)N([Si](C)(C)C)[Si](C)(C)C)C1	3209.9	Semi standard non polar	33892256
Tryptophylhydroxyproline,3TMS,isomer #3	C[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@H](CC2=C[NH]C3=CC=CC=C23)N([Si](C)(C)C)[Si](C)(C)C)C1	3168.0	Standard non polar	33892256
Tryptophylhydroxyproline,3TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O	3062.4	Semi standard non polar	33892256
Tryptophylhydroxyproline,3TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O	3065.3	Standard non polar	33892256
Tryptophylhydroxyproline,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	3165.5	Semi standard non polar	33892256
Tryptophylhydroxyproline,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	3102.2	Standard non polar	33892256
Tryptophylhydroxyproline,3TMS,isomer #6	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(=O)O[Si](C)(C)C	3020.9	Semi standard non polar	33892256
Tryptophylhydroxyproline,3TMS,isomer #6	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(=O)O[Si](C)(C)C	2986.2	Standard non polar	33892256
Tryptophylhydroxyproline,3TMS,isomer #7	C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(=O)O)[Si](C)(C)C	3188.0	Semi standard non polar	33892256
Tryptophylhydroxyproline,3TMS,isomer #7	C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(=O)O)[Si](C)(C)C	3129.5	Standard non polar	33892256
Tryptophylhydroxyproline,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@H](CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	3225.8	Semi standard non polar	33892256
Tryptophylhydroxyproline,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@H](CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	3149.1	Standard non polar	33892256
Tryptophylhydroxyproline,4TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C	3069.8	Semi standard non polar	33892256
Tryptophylhydroxyproline,4TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)N1C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)O[Si](C)(C)C	3023.1	Standard non polar	33892256
Tryptophylhydroxyproline,4TMS,isomer #3	C[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@H](CC2=CN([Si](C)(C)C)C3=CC=CC=C23)N([Si](C)(C)C)[Si](C)(C)C)C1	3223.4	Semi standard non polar	33892256
Tryptophylhydroxyproline,4TMS,isomer #3	C[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@H](CC2=CN([Si](C)(C)C)C3=CC=CC=C23)N([Si](C)(C)C)[Si](C)(C)C)C1	3178.0	Standard non polar	33892256
Tryptophylhydroxyproline,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	3192.2	Semi standard non polar	33892256
Tryptophylhydroxyproline,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	3112.2	Standard non polar	33892256
Tryptophylhydroxyproline,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	3263.3	Semi standard non polar	33892256
Tryptophylhydroxyproline,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)CN1C(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	3130.7	Standard non polar	33892256
Tryptophylhydroxyproline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@@H](N)CC2=C[NH]C3=CC=CC=C23)C1	3385.8	Semi standard non polar	33892256
Tryptophylhydroxyproline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H](N)CC1=C[NH]C2=CC=CC=C12	3321.1	Semi standard non polar	33892256
Tryptophylhydroxyproline,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(=O)O	3369.9	Semi standard non polar	33892256
Tryptophylhydroxyproline,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C=C(C[C@H](N)C(=O)N2C[C@H](O)C[C@H]2C(=O)O)C2=CC=CC=C21	3278.6	Semi standard non polar	33892256
Tryptophylhydroxyproline,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](N)CC1=C[NH]C2=CC=CC=C12	3587.3	Semi standard non polar	33892256
Tryptophylhydroxyproline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)O	3603.8	Semi standard non polar	33892256
Tryptophylhydroxyproline,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@@H](N)CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)C1	3528.1	Semi standard non polar	33892256
Tryptophylhydroxyproline,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3556.5	Semi standard non polar	33892256
Tryptophylhydroxyproline,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	3453.9	Semi standard non polar	33892256
Tryptophylhydroxyproline,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	3684.1	Semi standard non polar	33892256
Tryptophylhydroxyproline,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(=O)O	3523.7	Semi standard non polar	33892256
Tryptophylhydroxyproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)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	3782.9	Semi standard non polar	33892256
Tryptophylhydroxyproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)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	3647.1	Standard non polar	33892256
Tryptophylhydroxyproline,3TBDMS,isomer #2	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=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	3698.7	Semi standard non polar	33892256
Tryptophylhydroxyproline,3TBDMS,isomer #2	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=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	3485.4	Standard non polar	33892256
Tryptophylhydroxyproline,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@H](CC2=C[NH]C3=CC=CC=C23)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1	3943.0	Semi standard non polar	33892256
Tryptophylhydroxyproline,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@H](CC2=C[NH]C3=CC=CC=C23)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1	3748.8	Standard non polar	33892256
Tryptophylhydroxyproline,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)O	3744.1	Semi standard non polar	33892256
Tryptophylhydroxyproline,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)O	3637.0	Standard non polar	33892256
Tryptophylhydroxyproline,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3875.2	Semi standard non polar	33892256
Tryptophylhydroxyproline,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3708.2	Standard non polar	33892256
Tryptophylhydroxyproline,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3673.3	Semi standard non polar	33892256
Tryptophylhydroxyproline,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3580.8	Standard non polar	33892256
Tryptophylhydroxyproline,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	3867.8	Semi standard non polar	33892256
Tryptophylhydroxyproline,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	3703.0	Standard non polar	33892256
Tryptophylhydroxyproline,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](CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4131.4	Semi standard non polar	33892256
Tryptophylhydroxyproline,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](CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3865.1	Standard non polar	33892256
Tryptophylhydroxyproline,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)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	3867.5	Semi standard non polar	33892256
Tryptophylhydroxyproline,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)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	3712.9	Standard non polar	33892256
Tryptophylhydroxyproline,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@H](CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1	4098.2	Semi standard non polar	33892256
Tryptophylhydroxyproline,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)[C@H](CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1	3860.8	Standard non polar	33892256
Tryptophylhydroxyproline,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4024.3	Semi standard non polar	33892256
Tryptophylhydroxyproline,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3828.3	Standard non polar	33892256
Tryptophylhydroxyproline,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=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4257.1	Semi standard non polar	33892256
Tryptophylhydroxyproline,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=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3927.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tryptophylhydroxyproline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tryptophylhydroxyproline 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 - Tryptophylhydroxyproline 10V, Positive-QTOF	splash10-014i-0209000000-3d4ae2c12dea4fdab8f1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophylhydroxyproline 20V, Positive-QTOF	splash10-05mo-0902000000-4987df87b9ff1f6ea4ee	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophylhydroxyproline 40V, Positive-QTOF	splash10-0006-0900000000-7b9f6b4edc5922dd7854	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophylhydroxyproline 10V, Negative-QTOF	splash10-00kb-0296000000-b67a27ee6aaf400269d8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophylhydroxyproline 20V, Negative-QTOF	splash10-03xr-1922000000-db28d97fd64c94fbff40	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophylhydroxyproline 40V, Negative-QTOF	splash10-001l-4900000000-57794d687bce85a3e438	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

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

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

FDB112089

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

69042543

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 Tryptophylhydroxyproline (HMDB0029084)

MOL for HMDB0029084 (Tryptophylhydroxyproline)

3D MOL for HMDB0029084 (Tryptophylhydroxyproline)

3D SDF for HMDB0029084 (Tryptophylhydroxyproline)

3D-SDF for HMDB0029084 (Tryptophylhydroxyproline)

PDB for HMDB0029084 (Tryptophylhydroxyproline)

3D PDB for HMDB0029084 (Tryptophylhydroxyproline)

SMILES for HMDB0029084 (Tryptophylhydroxyproline)

INCHI for HMDB0029084 (Tryptophylhydroxyproline)

Structure for HMDB0029084 (Tryptophylhydroxyproline)

3D Structure for HMDB0029084 (Tryptophylhydroxyproline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra