Showing metabocard for Hydrocinnamic acid (MMDBc0000152)

Not Available
Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:37:46 UTC
Update Date2024-09-28 02:50:36 UTC
Metabolite IDMMDBc0000152
Metabolite Identification
Common NameHydrocinnamic acid
DescriptionHydrocinnamic acid, also known as phenylpropanoic acid, is an analogue of phenylalanine. It is a substrate of the enzyme oxidoreductases (EC 1.14.12.-) in the pathway phenylalanine metabolism (KEGG). Hydrocinnamic acid is a microbial metabolite and it can be found in Clostridium and Eubacterium (PMID: 28393285 , 7378938 ). It is a marker for the presence of Clostridium sporogenes in the gut. Higher levels are associated with higher levels of Clostridium sporogenes (PMID: 7378938 ). Hydrocinnamic acid is detected after the consumption of whole grain.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb0dc661b0>


  Mrv1652304272018552D          

 11 11  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8876    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3001    1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3001    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  2  0  0  0  0
  4  8  2  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fdb0dc661b0>

HMDB0000764
     RDKit          3D
Hydrocinnamic acid
 21 21  0  0  0  0  0  0  0  0999 V2000
    4.0705   -1.0791    0.7058 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2222   -0.4434    0.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5984    0.3955   -1.0301 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935   -0.6187    0.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9455    0.2186   -0.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4898    0.1193   -0.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3289   -0.8073   -0.8232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6725   -0.8484   -0.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2114    0.0454    0.3738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3920    0.9862    0.9651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0521    1.0034    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7015    1.4041   -0.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6797   -0.2031    1.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5109   -1.6691    0.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1641   -0.1439   -1.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2437    1.2760   -0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9336   -1.5302   -1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3465   -1.5822   -0.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2832    0.0151    0.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8115    1.7074    1.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4084    1.7545    1.1172 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  2  0
 11  6  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fdb0dc661b0>


  Mrv1652304272018552D          

 11 11  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8876    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3001    1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3001    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  2  0  0  0  0
  4  8  2  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000152

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11)

> <INCHI_KEY>
XMIIGOLPHOKFCH-UHFFFAOYSA-N

> <FORMULA>
C9H10O2

> <MOLECULAR_WEIGHT>
150.1745

> <EXACT_MASS>
150.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.943854511513758

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-phenylpropanoic acid

> <ALOGPS_LOGP>
1.84

> <JCHEM_LOGP>
2.0555627703333332

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.728925328917475

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
41.9666

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-phenylpropionic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x00007fdb0dc661b0>

HMDB0000764
     RDKit          3D
Hydrocinnamic acid
 21 21  0  0  0  0  0  0  0  0999 V2000
    4.0705   -1.0791    0.7058 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2222   -0.4434    0.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5984    0.3955   -1.0301 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935   -0.6187    0.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9455    0.2186   -0.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4898    0.1193   -0.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3289   -0.8073   -0.8232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6725   -0.8484   -0.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2114    0.0454    0.3738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3920    0.9862    0.9651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0521    1.0034    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7015    1.4041   -0.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6797   -0.2031    1.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5109   -1.6691    0.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1641   -0.1439   -1.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2437    1.2760   -0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9336   -1.5302   -1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3465   -1.5822   -0.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2832    0.0151    0.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8115    1.7074    1.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4084    1.7545    1.1172 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  2  0
 11  6  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
M  END
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PDB for #<Metabolite:0x00007fdb0dc661b0>

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.850   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.390   1.334   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -6.160   2.667   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -6.160   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    8                                                       
CONECT    6    7    8                                                       
CONECT    7    6    9                                                       
CONECT    8    4    5    6                                                  
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for #<Metabolite:0x00007fdb0dc661b0>

COMPND    HMDB0000764
HETATM    1  O1  UNL     1       4.070  -1.079   0.706  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.222  -0.443   0.028  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.598   0.396  -1.030  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.794  -0.619   0.397  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.945   0.219  -0.526  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.490   0.119  -0.249  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.329  -0.807  -0.823  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.673  -0.848  -0.520  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.211   0.045   0.374  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.392   0.986   0.965  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.052   1.003   0.642  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.701   1.404  -0.858  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.680  -0.203   1.423  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.511  -1.669   0.426  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.164  -0.144  -1.570  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.244   1.276  -0.431  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.934  -1.530  -1.536  1.00  0.00           H  
HETATM   18  H7  UNL     1      -3.346  -1.582  -0.972  1.00  0.00           H  
HETATM   19  H8  UNL     1      -4.283   0.015   0.618  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.811   1.707   1.682  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.408   1.754   1.117  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5   13   14
CONECT    5    6   15   16
CONECT    6    7    7   11
CONECT    7    8   17
CONECT    8    9    9   18
CONECT    9   10   19
CONECT   10   11   11   20
CONECT   11   21
END
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SMILES for #<Metabolite:0x00007fdb0dc661b0>

OC(=O)CCC1=CC=CC=C1
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INCHI for #<Metabolite:0x00007fdb0dc661b0>

InChI=1S/C9H10O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11)
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Synonyms
ValueSource
3-Phenyl-propionic acidChEBI
3-Phenylpropanoic acidChEBI
3-PhenylpropionsaeureChEBI
3PPChEBI
Benzenepropanoic acidChEBI
Benzenepropionic acidChEBI
Benzylacetic acidChEBI
beta-Phenylpropionic acidChEBI
Dihydrocinnamic acidChEBI
HydrozimtsaeureChEBI
PhenylpropanoateChEBI
3-PhenylpropanoateKegg
3-Phenylpropionic acidKegg
3-Phenyl-propionateGenerator
BenzenepropanoateGenerator
BenzenepropionateGenerator
BenzylacetateGenerator
b-PhenylpropionateGenerator
b-Phenylpropionic acidGenerator
beta-PhenylpropionateGenerator
Β-phenylpropionateGenerator
Β-phenylpropionic acidGenerator
DihydrocinnamateGenerator
Phenylpropanoic acidGenerator
3-PhenylpropionateGenerator
HydrocinnamateGenerator
3-Phenyl-N-propionateHMDB
3-Phenyl-N-propionic acidHMDB
Omega-phenylpropanoateHMDB
Omega-phenylpropanoic acidHMDB
W-PhenylpropanoateHMDB
W-Phenylpropanoic acidHMDB
3-Phenylpropionic acid, sodium saltHMDB
3-Phenyl propionic acidHMDB
Phenylpropionic acidHMDB
beta-Phenylpropanoic acidHMDB
Β-phenylpropanoic acidHMDB
Ω-phenylpropanoic acidHMDB
Molecular FormulaC9H10O2
Average Mass150.1745
Monoisotopic Mass150.068079564
IUPAC Name3-phenylpropanoic acid
Traditional Name3-phenylpropionic acid
CAS Registry Number501-52-0
SMILES
OC(=O)CCC1=CC=CC=C1
InChI Identifier
InChI=1S/C9H10O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11)
InChI KeyXMIIGOLPHOKFCH-UHFFFAOYSA-N