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Showing metabocard for Desaminotyrosine (HMDB0002199)

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enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:41 UTC
Update Date2023-02-21 17:16:15 UTC
HMDB IDHMDB0002199
Secondary Accession Numbers
  • HMDB0061145
  • HMDB02199
  • HMDB61145
Metabolite Identification
Common NameDesaminotyrosine
DescriptionDesaminotyrosine, also known as 4-hydroxyphenylpropionic acid, is a normal constituent of human urine. It is a product of tyrosine metabolism; its concentration in urine increases in patients with gastrointestinal diseases. Desaminotyrosine is a major phenolic acid breakdown product of proanthocyanidin metabolism (PMID:15315398 ). Urinary desaminotyrosine is produced by Clostridium sporogenes and C. botulinum (PMID:29168502 ). Desaminotyrosine is also found in Acinetobacter, Bacteroides, Bifidobacteria, Bifidobacterium, Clostridium, Enterococcus, Escherichia, Eubacterium, Klebsiella, Lactobacillus, Pseudomonas, and Staphylococcus (PMID:29168502 , 28393285 , 19961416 ). Desaminotyrosine is a phenolic acid metabolite formed by the gut microflora detected after the consumption of whole grain.
Structure
Data?1676999775
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002199 (Desaminotyrosine)


  Mrv1652309272007442D          

 12 12  0  0  0  0            999 V2000
 9994.8588 9994.9198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7181 9996.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4320 9996.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1481 9996.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8621 9996.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1481 9997.3955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0038 9996.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2895 9996.5696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5748 9996.1571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5748 9995.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2893 9994.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0038 9995.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12  7  1  0  0  0  0
  1 10  1  0  0  0  0
  7  2  1  0  0  0  0
  2  3  1  0  0  0  0
M  END
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3D MOL for HMDB0002199 (Desaminotyrosine)

HMDB0002199
     RDKit          3D
Desaminotyrosine
 22 22  0  0  0  0  0  0  0  0999 V2000
    3.9245   -1.1465    0.5746 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4159   -0.1462    0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1554    0.9986   -0.1174 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0190   -0.1791   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1497    0.0213    0.8294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2698    0.0033    0.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9062    1.1783    0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2330    1.1387   -0.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9316   -0.0290   -0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2666   -0.0267   -0.5377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3188   -1.2122    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9861   -1.1880    0.4689 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1352    1.8087    0.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7944    0.6581   -1.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7410   -1.1612   -0.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4848    1.0036    1.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4078   -0.7802    1.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3141    2.0900    0.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7441    2.0488   -0.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8632   -0.8363   -0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8942   -2.1198    0.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4999   -2.1241    0.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12  6  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  7 18  1  0
  8 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
M  END
Download

3D SDF for HMDB0002199 (Desaminotyrosine)


  Mrv1652309272007442D          

 12 12  0  0  0  0            999 V2000
 9994.8588 9994.9198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7181 9996.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4320 9996.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1481 9996.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8621 9996.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1481 9997.3955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0038 9996.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2895 9996.5696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5748 9996.1571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5748 9995.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2893 9994.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0038 9995.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12  7  1  0  0  0  0
  1 10  1  0  0  0  0
  7  2  1  0  0  0  0
  2  3  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002199

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CCC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12)

> <INCHI_KEY>
NMHMNPHRMNGLLB-UHFFFAOYSA-N

> <FORMULA>
C9H10O3

> <MOLECULAR_WEIGHT>
166.1739

> <EXACT_MASS>
166.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
16.971746796751624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-hydroxyphenyl)propanoic acid

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
1.7519974486666663

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.50593673911279

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.214213970870649

> <JCHEM_PKA_STRONGEST_BASIC>
-5.958297991799353

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
43.947500000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxyphenyl propionic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0002199 (Desaminotyrosine)

HMDB0002199
     RDKit          3D
Desaminotyrosine
 22 22  0  0  0  0  0  0  0  0999 V2000
    3.9245   -1.1465    0.5746 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4159   -0.1462    0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1554    0.9986   -0.1174 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0190   -0.1791   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1497    0.0213    0.8294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2698    0.0033    0.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9062    1.1783    0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2330    1.1387   -0.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9316   -0.0290   -0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2666   -0.0267   -0.5377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3188   -1.2122    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9861   -1.1880    0.4689 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1352    1.8087    0.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7944    0.6581   -1.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7410   -1.1612   -0.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4848    1.0036    1.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4078   -0.7802    1.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3141    2.0900    0.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7441    2.0488   -0.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8632   -0.8363   -0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8942   -2.1198    0.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4999   -2.1241    0.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12  6  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  7 18  1  0
  8 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
M  END
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PDB for HMDB0002199 (Desaminotyrosine)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8657.0708657.184   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8662.4078660.264   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8663.7408659.494   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8665.0768660.264   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8666.4098659.494   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8665.0768661.805   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8661.0748659.493   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8659.7408660.263   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8658.4068659.493   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8658.4068657.953   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8659.7408657.183   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.0748657.953   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2    7    3                                                       
CONECT    3    4    2                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    8   12    2                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11    1                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0002199 (Desaminotyrosine)

COMPND    HMDB0002199
HETATM    1  O1  UNL     1       3.924  -1.147   0.575  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.416  -0.146   0.043  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.155   0.999  -0.117  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.019  -0.179  -0.420  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.150   0.021   0.829  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.270   0.003   0.471  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.906   1.178   0.133  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.233   1.139  -0.198  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.932  -0.029  -0.199  1.00  0.00           C  
HETATM   10  O3  UNL     1      -4.267  -0.027  -0.538  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.319  -1.212   0.135  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.986  -1.188   0.469  1.00  0.00           C  
HETATM   13  H1  UNL     1       4.135   1.809   0.488  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.794   0.658  -1.117  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.741  -1.161  -0.853  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.485   1.004   1.250  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.408  -0.780   1.548  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.314   2.090   0.145  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.744   2.049  -0.465  1.00  0.00           H  
HETATM   20  H8  UNL     1      -4.863  -0.836  -0.567  1.00  0.00           H  
HETATM   21  H9  UNL     1      -2.894  -2.120   0.124  1.00  0.00           H  
HETATM   22  H10 UNL     1      -0.500  -2.124   0.732  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5   14   15
CONECT    5    6   16   17
CONECT    6    7    7   12
CONECT    7    8   18
CONECT    8    9    9   19
CONECT    9   10   11
CONECT   10   20
CONECT   11   12   12   21
CONECT   12   22
END
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SMILES for HMDB0002199 (Desaminotyrosine)

OC(=O)CCC1=CC=C(O)C=C1
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INCHI for HMDB0002199 (Desaminotyrosine)

InChI=1S/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
3-(p-Hydroxyphenyl)propionic acidChEBI
4-Hydroxyphenylpropionic acidChEBI
beta-(p-Hydroxyphenyl)propionic acidChEBI
Dihydro-p-coumaric acidChEBI
HYDROXYPHENYL propionIC ACIDChEBI
p-Hydroxyhydrocinnamic acidChEBI
p-Hydroxyphenylpropionic acidChEBI
Phloretinic acidChEBI
3-(4-Hydroxyphenyl)propanoateKegg
3-(4-Hydroxyphenyl)propionateGenerator
3-(p-Hydroxyphenyl)propionateGenerator
4-HydroxyphenylpropionateGenerator
b-(p-Hydroxyphenyl)propionateGenerator
b-(p-Hydroxyphenyl)propionic acidGenerator
beta-(p-Hydroxyphenyl)propionateGenerator
Β-(p-hydroxyphenyl)propionateGenerator
Β-(p-hydroxyphenyl)propionic acidGenerator
Dihydro-p-coumarateGenerator
HYDROXYPHENYL propionateGenerator
p-HydroxyhydrocinnamateGenerator
p-HydroxyphenylpropionateGenerator
PhloretinateGenerator
PhloretateGenerator
3-(4-Hydroxyphenyl)propanoic acidGenerator
3-(4'-Hydroxyphenyl)-propionateHMDB
3-(4'-Hydroxyphenyl)-propionic acidHMDB
3-(4'-Hydroxyphenyl)propionic acidHMDB
3-(4-Hydroxy-phenyl)-propionateHMDB
3-(4-Hydroxy-phenyl)-propionic acidHMDB
3-(4-Hydroxyphenyl)-propionateHMDB
3-(4-Hydroxyphenyl)-propionic acidHMDB
3-(Para-hydroxyphenyl)propionateHMDB
3-(Para-hydroxyphenyl)propionic acidHMDB
4'-Hydroxyphenylpropionic acidHMDB
4-(4-HydroxyphenylpropanoateHMDB
4-(4-Hydroxyphenylpropanoic acidHMDB
4-Hydroxy-(9ci)benzenepropanoateHMDB
4-Hydroxy-(9ci)benzenepropanoic acidHMDB
4-Hydroxy-benzenepropanoateHMDB
4-Hydroxy-benzenepropanoic acidHMDB
4-HydroxybenzenepropanoateHMDB
4-Hydroxybenzenepropanoic acidHMDB
hydro-P-CoumarateHMDB
Hydro-p-coumaric acidHMDB
Hydroxy-hydrocinnamic acidHMDB
N-Hydroxysuccinimide esterHMDB
P-Hydroxy-benzene propionateHMDB
P-Hydroxy-benzene propionic acidHMDB
P-Hydroxy-hydrocinnamateHMDB
P-Hydroxy-hydrocinnamic acidHMDB
4-Hydroxyhydrocinnamic acidMeSH, HMDB
DesaminotyrosineChEBI
3-(4'-Hydroxyphenyl)propanoic acidPhytoBank
4-Hydroxybenzenepropionic acidPhytoBank
2,3-Dihydro-p-coumaric acidPhytoBank
3-(4’-Hydroxyphenyl)propanoic acidPhytoBank
3-(4’-Hydroxyphenyl)propionic acidPhytoBank
3-(p-Hydroxyphenyl)propanoic acidPhytoBank
4-(2-Carboxyethyl)phenolPhytoBank
4-(2-Carboxylethyl)phenolPhytoBank
4-Hydroxydihydrocinnamic acidPhytoBank
Dihydrocoumaric acidPhytoBank
p-Hydroxybenzene propanoic acidPhytoBank
p-Hydroxybenzene propionic acidPhytoBank
p-Hydroxyphenylpropanoic acidPhytoBank
beta-(4-Hydroxyphenyl)propanoic acidPhytoBank
beta-(4-Hydroxyphenyl)propionic acidPhytoBank
β-(4-Hydroxyphenyl)propanoic acidPhytoBank
β-(4-Hydroxyphenyl)propionic acidPhytoBank
beta-(p-Hydroxyphenyl)propanoic acidPhytoBank
β-(p-Hydroxyphenyl)propanoic acidPhytoBank
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name3-(4-hydroxyphenyl)propanoic acid
Traditional Namehydroxyphenyl propionic acid
CAS Registry Number501-97-3
SMILES
OC(=O)CCC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12)
InChI KeyNMHMNPHRMNGLLB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point129 °CNot Available
Boiling Point352.40 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility61820 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.16HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.71 g/LALOGPS
logP1.15ALOGPS
logP1.75ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)4.21ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.95 m³·mol⁻¹ChemAxon
Polarizability16.97 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.18831661259
DarkChem[M-H]-133.3931661259
DeepCCS[M+H]+135.36130932474
DeepCCS[M-H]-132.41830932474
DeepCCS[M-2H]-169.33930932474
DeepCCS[M+Na]+144.87730932474
AllCCS[M+H]+135.832859911
AllCCS[M+H-H2O]+131.432859911
AllCCS[M+NH4]+139.832859911
AllCCS[M+Na]+141.032859911
AllCCS[M-H]-135.232859911
AllCCS[M+Na-2H]-136.232859911
AllCCS[M+HCOO]-137.432859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.3.82 minutes32390414
Predicted by Siyang on May 30, 202210.1204 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.56 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid41.3 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1277.1 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid317.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid123.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid187.9 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid149.6 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid386.9 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid367.0 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)107.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid812.0 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid344.7 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1023.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid249.9 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid284.8 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate455.3 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA205.4 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water146.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DesaminotyrosineOC(=O)CCC1=CC=C(O)C=C13193.2Standard polar33892256
DesaminotyrosineOC(=O)CCC1=CC=C(O)C=C11649.6Standard non polar33892256
DesaminotyrosineOC(=O)CCC1=CC=C(O)C=C11659.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Desaminotyrosine,1TMS,isomer #1C[Si](C)(C)OC(=O)CCC1=CC=C(O)C=C11778.2Semi standard non polar33892256
Desaminotyrosine,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(CCC(=O)O)C=C11752.1Semi standard non polar33892256
Desaminotyrosine,2TMS,isomer #1C[Si](C)(C)OC(=O)CCC1=CC=C(O[Si](C)(C)C)C=C11772.6Semi standard non polar33892256
Desaminotyrosine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1=CC=C(O)C=C12007.6Semi standard non polar33892256
Desaminotyrosine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(=O)O)C=C11992.3Semi standard non polar33892256
Desaminotyrosine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12269.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Desaminotyrosine EI-B (Non-derivatized)splash10-066r-9800000000-44e113d8fc2602ffba882017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Desaminotyrosine GC-EI-TOF (Non-derivatized)splash10-004l-0900000000-5ae3f727b5218398aa832017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Desaminotyrosine EI-B (Non-derivatized)splash10-066r-9800000000-44e113d8fc2602ffba882018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Desaminotyrosine GC-EI-TOF (Non-derivatized)splash10-004l-0900000000-5ae3f727b5218398aa832018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Desaminotyrosine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-3900000000-424e95de0b8037c4aa202017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Desaminotyrosine GC-MS (2 TMS) - 70eV, Positivesplash10-00g0-9660000000-261dcfd72b0dbd1c03df2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Desaminotyrosine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Desaminotyrosine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00kv-5900000000-db98339dadc21116c7aa2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desaminotyrosine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-052r-9400000000-7d2340d4f6981ee8aecb2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desaminotyrosine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-00bi-9100000000-cac6ca239c2cbe36238d2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desaminotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-014i-0900000000-e131522c5a7352167afb2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desaminotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-014i-3900000000-5c5920f4693d31baa6402012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desaminotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0a4i-9500000000-49bd07916272cdc49e682012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desaminotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0a6u-9100000000-683b03c9384a9a7508632012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desaminotyrosine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-00di-9000000000-d4af6cba1b370fd620ed2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desaminotyrosine LC-ESI-QQ , negative-QTOFsplash10-014i-0900000000-514be816ed648e5588b72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desaminotyrosine LC-ESI-QQ , negative-QTOFsplash10-014i-3900000000-5c5920f4693d31baa6402017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desaminotyrosine LC-ESI-QQ , negative-QTOFsplash10-0a4i-9500000000-49bd07916272cdc49e682017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desaminotyrosine LC-ESI-QQ , negative-QTOFsplash10-0a6u-9100000000-683b03c9384a9a7508632017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desaminotyrosine LC-ESI-QQ , negative-QTOFsplash10-00di-9000000000-d4af6cba1b370fd620ed2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desaminotyrosine 10V, Positive-QTOFsplash10-014j-0900000000-3603746465916eaf1e982017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desaminotyrosine 20V, Positive-QTOFsplash10-0601-1900000000-a85683e512fff2c291dd2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desaminotyrosine 40V, Positive-QTOFsplash10-0kdi-9500000000-dbb0fa659379ccf4eb262017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desaminotyrosine 10V, Negative-QTOFsplash10-014i-0900000000-17bb794e8bbfe1aad6b32017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desaminotyrosine 20V, Negative-QTOFsplash10-01b9-1900000000-9708817125183e0214a32017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desaminotyrosine 40V, Negative-QTOFsplash10-0a4l-9400000000-d9a164ed2938481885d92017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desaminotyrosine 10V, Negative-QTOFsplash10-066r-5900000000-6672a989c0ad56cb16972021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desaminotyrosine 20V, Negative-QTOFsplash10-05fu-8900000000-f2a5c52c26b284a94a512021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desaminotyrosine 40V, Negative-QTOFsplash10-0006-9300000000-179e6648decb5dd319532021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desaminotyrosine 10V, Positive-QTOFsplash10-0aba-0900000000-3631ad60fd3a5053aacf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desaminotyrosine 20V, Positive-QTOFsplash10-0a4i-2900000000-28c2e194d667a26ec1522021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desaminotyrosine 40V, Positive-QTOFsplash10-004i-9300000000-20c3b533b0eccb02601e2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Kidney
  • Liver
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry details
BloodDetected and Quantified3.189 +/- 2.633 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.574 +/- 0.078 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.69 +/- 0.099 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.701 +/- 0.071 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.705 +/- 0.1 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.712 +/- 0.088 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.628 +/- 0.075 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.664 +/- 0.089 uMAdult (>18 years old)Male
Normal		 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
FecesDetected and Quantified131.790 +/- 93.878 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified143.825 +/- 106.515 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified184.746 +/- 169.702 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified76.426 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified16.128 +/- 15.165 nmol/g wet fecesNot SpecifiedNot Specified
Normal		 details
FecesDetected and Quantified25.877 +/- 30.0890 nmol/g wet fecesNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal		 details
FecesDetected and Quantified84.249 (62.465-111.931) nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected and Quantified1.03 +/- 1.26 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified2.02 +/- 2.48 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected and Quantified1.32 +/- 2.81 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified1.59 +/- 2.05 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified1.64 +/- 1.89 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified3.11 +/- 5.21 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal details
UrineDetected and Quantified0.2 +/- 0.041 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
UrineDetected and Quantified0.089 +/- 0.016 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
UrineDetected and Quantified0.078 +/- 0.009 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Irritable bowel syndrome		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Irritable bowel syndrome		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCCD details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothIleal Crohn's disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleMissing teeth details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleSupragingival Plaque details
Associated Disorders and Diseases
Disease References
Irritable bowel syndrome
  1. Ponnusamy K, Choi JN, Kim J, Lee SY, Lee CH: Microbial community and metabolomic comparison of irritable bowel syndrome faeces. J Med Microbiol. 2011 Jun;60(Pt 6):817-27. doi: 10.1099/jmm.0.028126-0. Epub 2011 Feb 17. [PubMed:21330412 ]
  2. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Ulcerative colitis
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Missing teeth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Supragingival Plaque
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Associated OMIM IDs
DrugBank IDDB03897
Phenol Explorer Compound ID578
FooDB IDFDB000849
KNApSAcK IDC00029471
Chemspider ID9965
KEGG Compound IDC01744
BioCyc ID2-3-DIHYDROXYPHENYL-PROPIONATE
BiGG IDNot Available
Wikipedia LinkPhloretic acid
METLIN ID4148
PubChem Compound10394
PDB IDNot Available
ChEBI ID32980
Food Biomarker OntologyNot Available
VMH IDPHPPA
MarkerDB IDNot Available
Good Scents IDrw1185981
References
Synthesis ReferenceJin, Enqing. Preparation of 4-hydroxyphenylpropionic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (1998), 5 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Vickers S, Stuart EK, Hucker HB: Further studies on the metabolism of carbidopa, (minus)-L-alpha-hydrazino-3,4-dihydroxy-alpha-methylbenzenepropanoic acid monohydrate, in the human, Rhesus monkey, dog, and rat. J Med Chem. 1975 Feb;18(2):134-8. [PubMed:804550 ]
  2. Mel'nikova YaI, Kravchuk ZI, Preygerzon VA, Martsev SP: Functional activation of antibodies on modification with Pd(II) coproporphyrin I N-Hydroxysuccinimide ester. Biochemistry (Mosc). 1997 Aug;62(8):924-7. [PubMed:9360305 ]
  3. Herr JC, Woodward MP: An enzyme-linked immunosorbent assay (ELISA) for human semen identification based on a biotinylated monoclonal antibody to a seminal vesicle-specific antigen. J Forensic Sci. 1987 Mar;32(2):346-56. [PubMed:3572333 ]
  4. Ward NC, Croft KD, Puddey IB, Hodgson JM: Supplementation with grape seed polyphenols results in increased urinary excretion of 3-hydroxyphenylpropionic Acid, an important metabolite of proanthocyanidins in humans. J Agric Food Chem. 2004 Aug 25;52(17):5545-9. [PubMed:15315398 ]
  5. Neurath AR, Strick N, Szmuness W, Stevens CE, Harley EJ: Radioimmunoassay of hepatitis B e-antigen (HBeAg): identification of HBeAg not associated with immunoglobulins. J Gen Virol. 1979 Mar;42(3):493-504. [PubMed:107272 ]
  6. Fargeas C, Hommel M, Maingon R, Dourado C, Monsigny M, Mayer R: Synthetic peptide-based enzyme-linked immunosorbent assay for serodiagnosis of visceral leishmaniasis. J Clin Microbiol. 1996 Feb;34(2):241-8. [PubMed:8788994 ]
  7. Beloborodova NV, Khodakova AS, Bairamov IT, Olenin AY: Microbial origin of phenylcarboxylic acids in the human body. Biochemistry (Mosc). 2009 Dec;74(12):1350-5. [PubMed:19961416 ]
  8. Rowland I, Gibson G, Heinken A, Scott K, Swann J, Thiele I, Tuohy K: Gut microbiota functions: metabolism of nutrients and other food components. Eur J Nutr. 2018 Feb;57(1):1-24. doi: 10.1007/s00394-017-1445-8. Epub 2017 Apr 9. [PubMed:28393285 ]
  9. Dodd D, Spitzer MH, Van Treuren W, Merrill BD, Hryckowian AJ, Higginbottom SK, Le A, Cowan TM, Nolan GP, Fischbach MA, Sonnenburg JL: A gut bacterial pathway metabolizes aromatic amino acids into nine circulating metabolites. Nature. 2017 Nov 30;551(7682):648-652. doi: 10.1038/nature24661. Epub 2017 Nov 22. [PubMed:29168502 ]
  10. Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Desaminotyrosine → 6-[4-(2-carboxyethyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Desaminotyrosine → 3,4,5-trihydroxy-6-{[3-(4-hydroxyphenyl)propanoyl]oxy}oxane-2-carboxylic aciddetails
Enzyme Details
2. Sulfotransferase 1A3
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Desaminotyrosine → 3-[4-(sulfooxy)phenyl]propanoic aciddetails