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Showing metabocard for 3-(3-Hydroxyphenyl)propanoic acid (HMDB0000375)

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enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:46 UTC
HMDB IDHMDB0000375
Secondary Accession Numbers
  • HMDB00375
Metabolite Identification
Common Name3-(3-Hydroxyphenyl)propanoic acid
Description3-(3-Hydroxyphenyl)propanoic (hMPP) acid is one of the major metabolites of ingested caffeic acid (PMID: 15479001 ) and of the phenolic degradation products of proanthocyanidins (the most abundant polyphenol present in chocolate) by the microflora in the colon (PMID: 12663291 ). mHPP is suspected to have antioxidants properties and is actively absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers (PMID: 15479001 , 12663291 ). hMPP has been found to be a metabolite of Clostridium, Escherichia, and Eubacterium (PMID: 28393285 , 19520845 ). 3-(3-Hydroxyphenyl)propanoic acid is a flavonoid metabolite. 3-(3-Hydroxyphenyl)propanoic acid is a phenolic acid metabolite formed by the gut microflora detected after the consumption of whole grain.
Structure
Data?1676999686
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000375 (3-(3-Hydroxyphenyl)propanoic acid)


  Mrv1652306181900072D          

 12 12  0  0  0  0            999 V2000
10000.014610000.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7294 9999.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.014610001.2359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8713 9999.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.156710000.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4423 9999.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4423 9999.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1567 9998.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8713 9999.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3002 9999.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.585610000.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.727810000.4111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9  4  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11  4  1  0  0  0  0
  6 12  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000375 (3-(3-Hydroxyphenyl)propanoic acid)

HMDB0000375
     RDKit          3D
3-(3-Hydroxyphenyl)propanoic acid
 22 22  0  0  0  0  0  0  0  0999 V2000
    3.6945    0.6950    1.3078 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3440    0.4683    0.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2764    0.0624   -0.8015 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9385    0.6298   -0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1063   -0.2086    0.6255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200   -0.2112    0.4069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8187   -1.1427   -0.5080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1370   -1.2779   -0.8229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0633   -0.4563   -0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5903    0.4850    0.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5300    1.2948    1.3004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2476    0.5991    1.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4093   -0.9741   -0.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7334    1.7149   -0.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8369    0.3429   -1.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846    0.0843    1.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4878   -1.2487    0.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1209   -1.8154   -1.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5119   -2.0028   -1.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1141   -0.5353   -0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7730    2.1759    0.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8849    1.3203    1.7136 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
 10 11  1  0
 10 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
  9 20  1  0
 11 21  1  0
 12 22  1  0
M  END
Download

3D SDF for HMDB0000375 (3-(3-Hydroxyphenyl)propanoic acid)


  Mrv1652306181900072D          

 12 12  0  0  0  0            999 V2000
10000.014610000.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7294 9999.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.014610001.2359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8713 9999.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.156710000.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4423 9999.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4423 9999.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1567 9998.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8713 9999.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3002 9999.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.585610000.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.727810000.4111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9  4  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11  4  1  0  0  0  0
  6 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000375

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
QVWAEZJXDYOKEH-UHFFFAOYSA-N

> <FORMULA>
C9H10O3

> <MOLECULAR_WEIGHT>
166.1739

> <EXACT_MASS>
166.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
16.91566623086139

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.14

> <JCHEM_LOGP>
1.7519974486666663

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.466811432900812

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.214566239011227

> <JCHEM_PKA_STRONGEST_BASIC>
-5.964060407587341

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
43.947500000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxyphenylpropionic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000375 (3-(3-Hydroxyphenyl)propanoic acid)

HMDB0000375
     RDKit          3D
3-(3-Hydroxyphenyl)propanoic acid
 22 22  0  0  0  0  0  0  0  0999 V2000
    3.6945    0.6950    1.3078 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3440    0.4683    0.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2764    0.0624   -0.8015 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9385    0.6298   -0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1063   -0.2086    0.6255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200   -0.2112    0.4069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8187   -1.1427   -0.5080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1370   -1.2779   -0.8229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0633   -0.4563   -0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5903    0.4850    0.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5300    1.2948    1.3004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2476    0.5991    1.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4093   -0.9741   -0.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7334    1.7149   -0.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8369    0.3429   -1.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846    0.0843    1.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4878   -1.2487    0.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1209   -1.8154   -1.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5119   -2.0028   -1.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1141   -0.5353   -0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7730    2.1759    0.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8849    1.3203    1.7136 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
 10 11  1  0
 10 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
  9 20  1  0
 11 21  1  0
 12 22  1  0
M  END
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PDB for HMDB0000375 (3-(3-Hydroxyphenyl)propanoic acid)

HEADER    PROTEIN                                 18-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-JUN-19         0                                  
HETATM    1  C   UNK     0    8666.6948667.435   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8668.0288666.666   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8666.6948668.974   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8662.6938666.664   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8661.3598667.434   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8660.0268666.664   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8660.0268665.124   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8661.3598664.354   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.6938665.124   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8665.3608666.665   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.0268667.434   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8658.6928667.434   0.000  0.00  0.00           O+0
CONECT    1    2    3   10                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    5    9   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    1   11                                                       
CONECT   11   10    4                                                       
CONECT   12    6                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0000375 (3-(3-Hydroxyphenyl)propanoic acid)

COMPND    HMDB0000375
HETATM    1  O1  UNL     1       3.695   0.695   1.308  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.344   0.468   0.129  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.276   0.062  -0.802  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.939   0.630  -0.269  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.106  -0.209   0.625  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.320  -0.211   0.407  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.819  -1.143  -0.508  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.137  -1.278  -0.823  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.063  -0.456  -0.215  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.590   0.485   0.706  1.00  0.00           C  
HETATM   11  O3  UNL     1      -3.530   1.295   1.300  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.248   0.599   1.004  1.00  0.00           C  
HETATM   13  H1  UNL     1       4.409  -0.974  -0.857  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.733   1.715  -0.222  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.837   0.343  -1.334  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.285   0.084   1.697  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.488  -1.249   0.556  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.121  -1.815  -1.019  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.512  -2.003  -1.531  1.00  0.00           H  
HETATM   20  H8  UNL     1      -4.114  -0.535  -0.433  1.00  0.00           H  
HETATM   21  H9  UNL     1      -3.773   2.176   0.863  1.00  0.00           H  
HETATM   22  H10 UNL     1      -0.885   1.320   1.714  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   20
CONECT   10   11   12   12
CONECT   11   21
CONECT   12   22
END
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SMILES for HMDB0000375 (3-(3-Hydroxyphenyl)propanoic acid)

OC(=O)CCC1=CC(O)=CC=C1
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INCHI for HMDB0000375 (3-(3-Hydroxyphenyl)propanoic acid)

InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
3-(3-Hydroxy-phenyl)-propanoic acidChEBI
3-(m-Hydroxyphenyl)propionic acidChEBI
beta-(m-Hydroxyphenyl)propionic acidChEBI
Dihydro-3-coumaric acidChEBI
3-HydroxyphenylpropanoateKegg
3-(3-Hydroxyphenyl)propanoateKegg
3-(3-Hydroxy-phenyl)-propanoateGenerator
3-(3-Hydroxyphenyl)propionateGenerator
3-(m-Hydroxyphenyl)propionateGenerator
b-(m-Hydroxyphenyl)propionateGenerator
b-(m-Hydroxyphenyl)propionic acidGenerator
beta-(m-Hydroxyphenyl)propionateGenerator
Β-(m-hydroxyphenyl)propionateGenerator
Β-(m-hydroxyphenyl)propionic acidGenerator
Dihydro-3-coumarateGenerator
3-Hydroxyphenylpropanoic acidGenerator
3-(3-Hydroxy-phenyl)-propionic acidHMDB
3-HydroxybenzenepropanoateHMDB
3-Hydroxybenzenepropanoic acidHMDB
3-HydroxydihydrocinnamateHMDB
3-Hydroxydihydrocinnamic acidHMDB
3-Hydroxyhydrocinnamic acidHMDB
3-HydroxyphenylpropionateHMDB
3-Hydroxyphenylpropionic acidHMDB
b-(3-Hydroxyphenyl)propionateHMDB
b-(3-Hydroxyphenyl)propionic acidHMDB
beta-(3-Hydroxyphenyl)propionateHMDB
beta-(3-Hydroxyphenyl)propionic acidHMDB
dihydro-m-CoumarateHMDB
dihydro-m-Coumaric acidHMDB, MeSH
m-Hydrocoumaric acidHMDB
m-Hydroxy-hydrocinnamateHMDB
m-Hydroxy-hydrocinnamic acidHMDB
m-HydroxyphenylpropionateHMDB
m-Hydroxyphenylpropionic acidHMDB, MeSH
dihydro-3-Coumaric acid, monosodium saltMeSH, HMDB
3-(3'-Hydroxyphenyl)propanoic acidHMDB
3-(3-Hydroxyphenyl)propanoic acidHMDB
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name3-(3-hydroxyphenyl)propanoic acid
Traditional Name3-hydroxyphenylpropionic acid
CAS Registry Number621-54-5
SMILES
OC(=O)CCC1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12)
InChI KeyQVWAEZJXDYOKEH-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-4-unsubstituted benzenoid
  • 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 effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility17370 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg136.11430932474
[M-H]-Not Available136.114http://allccs.zhulab.cn/database/detail?ID=AllCCS00000426
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.8 g/LALOGPS
logP1.14ALOGPS
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
Polarizability16.92 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]+137.28731661259
DarkChem[M-H]-133.02431661259
AllCCS[M+H]+135.58932859911
AllCCS[M-H]-134.13232859911
DeepCCS[M+H]+134.26730932474
DeepCCS[M-H]-131.48430932474
DeepCCS[M-2H]-167.99630932474
DeepCCS[M+Na]+143.42230932474
AllCCS[M+H]+135.632859911
AllCCS[M+H-H2O]+131.232859911
AllCCS[M+NH4]+139.732859911
AllCCS[M+Na]+140.832859911
AllCCS[M-H]-134.132859911
AllCCS[M+Na-2H]-135.132859911
AllCCS[M+HCOO]-136.332859911

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, 2022.3.54 minutes32390414
Predicted by Siyang on May 30, 202210.2084 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.28 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid41.4 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1303.7 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid320.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid124.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid191.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid157.7 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid392.7 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 Acid369.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)104.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid825.0 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid343.9 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1024.6 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid252.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid287.6 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate442.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA215.6 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water133.7 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-(3-Hydroxyphenyl)propanoic acidOC(=O)CCC1=CC(O)=CC=C13087.2Standard polar33892256
3-(3-Hydroxyphenyl)propanoic acidOC(=O)CCC1=CC(O)=CC=C11631.9Standard non polar33892256
3-(3-Hydroxyphenyl)propanoic acidOC(=O)CCC1=CC(O)=CC=C11671.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-(3-Hydroxyphenyl)propanoic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCC1=CC=CC(O)=C11764.1Semi standard non polar33892256
3-(3-Hydroxyphenyl)propanoic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC=CC(CCC(=O)O)=C11736.4Semi standard non polar33892256
3-(3-Hydroxyphenyl)propanoic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCC1=CC=CC(O[Si](C)(C)C)=C11730.0Semi standard non polar33892256
3-(3-Hydroxyphenyl)propanoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1=CC=CC(O)=C11992.4Semi standard non polar33892256
3-(3-Hydroxyphenyl)propanoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC(CCC(=O)O)=C11970.2Semi standard non polar33892256
3-(3-Hydroxyphenyl)propanoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C12199.7Semi standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified0.775 +/- 0.747 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.034 +/- 0.01 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.039 +/- 0.012 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.04 +/- 0.008 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.084 +/- 0.022 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.086 +/- 0.021 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.035 +/- 0.008 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.056 +/- 0.015 uMAdult (>18 years old)Male
Normal		 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 961 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 961 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified9.0508 (0.0722-110.366) nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified74.0188 +/- 139.0110 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal 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 QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
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 and Quantified290.659 +/- 834.0660 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified288.854 +/- 717.321 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified105.913 +/- 182.941 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.32 (0.2 - 0.5) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.043 +/- 0.006 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 961 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 961 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.5 +/- 0.46 umol/mmol creatinineAdult (>18 years old)BothNormal 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)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specifiedasymptomatic diverticulosis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specifiedsymptomatic uncomplicated diverticular disease details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Hypertension (mild)		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Hypertension (mild)		 details
UrineDetected and Quantified2.292 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified1.325 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
 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 ]
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 ]
Diverticular disease
  1. Tursi A, Mastromarino P, Capobianco D, Elisei W, Miccheli A, Capuani G, Tomassini A, Campagna G, Picchio M, Giorgetti G, Fabiocchi F, Brandimarte G: Assessment of Fecal Microbiota and Fecal Metabolome in Symptomatic Uncomplicated Diverticular Disease of the Colon. J Clin Gastroenterol. 2016 Oct;50 Suppl 1:S9-S12. doi: 10.1097/MCG.0000000000000626. [PubMed:27622378 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021993
KNApSAcK IDC00052683
Chemspider ID89
KEGG Compound IDC11457
BioCyc ID3-HYDROXYPHENYL-PROPIONATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91
PDB IDNot Available
ChEBI ID1427
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1417091
References
Synthesis ReferenceDombrow, M.; Linnell, W. H. Preparation of m-hydroxyphenylpropionic acid. Journal of Pharmacy and Pharmacology (1952), 4 118-19.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Nakazawa T, Ohsawa K: Metabolites of orally administered Perilla frutescens extract in rats and humans. Biol Pharm Bull. 2000 Jan;23(1):122-7. [PubMed:10706426 ]
  2. Duran M, Wanders RJ, de Jager JP, Dorland L, Bruinvis L, Ketting D, Ijlst L, van Sprang FJ: 3-Hydroxydicarboxylic aciduria due to long-chain 3-hydroxyacyl-coenzyme A dehydrogenase deficiency associated with sudden neonatal death: protective effect of medium-chain triglyceride treatment. Eur J Pediatr. 1991 Jan;150(3):190-5. [PubMed:2044590 ]
  3. Rios LY, Gonthier MP, Remesy C, Mila I, Lapierre C, Lazarus SA, Williamson G, Scalbert A: Chocolate intake increases urinary excretion of polyphenol-derived phenolic acids in healthy human subjects. Am J Clin Nutr. 2003 Apr;77(4):912-8. [PubMed:12663291 ]
  4. Konishi Y, Kobayashi S: Microbial metabolites of ingested caffeic acid are absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers. J Agric Food Chem. 2004 Oct 20;52(21):6418-24. [PubMed:15479001 ]
  5. 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 ]
  6. Manso I, Torres B, Andreu JM, Menendez M, Rivas G, Alfonso C, Diaz E, Garcia JL, Galan B: 3-Hydroxyphenylpropionate and phenylpropionate are synergistic activators of the MhpR transcriptional regulator from Escherichia coli. J Biol Chem. 2009 Aug 7;284(32):21218-28. doi: 10.1074/jbc.M109.008243. Epub 2009 Jun 11. [PubMed:19520845 ]
  7. Upadhyaya S, Banerjee G: Type 2 diabetes and gut microbiome: at the intersection of known and unknown. Gut Microbes. 2015;6(2):85-92. doi: 10.1080/19490976.2015.1024918. [PubMed:25901889 ]
  8. 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
3-(3-Hydroxyphenyl)propanoic acid → 6-[3-(2-carboxyethyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3-(3-Hydroxyphenyl)propanoic acid → 3,4,5-trihydroxy-6-{[3-(3-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
3-(3-Hydroxyphenyl)propanoic acid → 3-[3-(Sulfooxy)phenyl]propanoic aciddetails