Showing metabocard for 3-(3-Hydroxyphenyl)propanoic acid (MMDBc0000514)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:39:30 UTC
Update Date2024-04-30 19:32:44 UTC
Metabolite IDMMDBc0000514
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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f92302d72a0>


  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 #<Metabolite:0x00007f92302d72a0>

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 #<Metabolite:0x00007f92302d72a0>


  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>
MMDBc0000514

> <DATABASE_NAME>
MIME

> <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

$$$$
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3D-SDF for #<Metabolite:0x00007f92302d72a0>

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

PDB for #<Metabolite:0x00007f92302d72a0>

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 #<Metabolite:0x00007f92302d72a0>

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 #<Metabolite:0x00007f92302d72a0>

OC(=O)CCC1=CC(O)=CC=C1
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INCHI for #<Metabolite:0x00007f92302d72a0>

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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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
Molecular FormulaC9H10O3
Average Mass166.1739
Monoisotopic Mass166.062994186
IUPAC Name3-(3-hydroxyphenyl)propanoic acid
Traditional Name3-hydroxyphenylpropionic acid
CAS Registry NumberNot Available
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