Showing metabocard for 3,4-Dihydroxyhydrocinnamic acid (MMDBc0000516)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:39:32 UTC
Update Date2024-09-27 20:52:23 UTC
Metabolite IDMMDBc0000516
Metabolite Identification
Common Name3,4-Dihydroxyhydrocinnamic acid
Description3,4-Dihydroxyhydrocinnamic acid, also known as dihydrocaffeic acid (DHCA), is a metabolite product of the hydrogenation of caffeoylquinic acids, occurring in normal human biofluids, with potent antioxidant properties. DHCA has been detected in human plasma following coffee ingestion (PMID: 15607645 ) and is increased with some dietary sources, such as after ingestion of phenolic constituents of artichoke leaf extract (PMID: 15693705 ). Polyphenol-rich foods such as vegetables and fruits have been shown to significantly improve platelet function in ex vivo studies in humans (PMID: 16038718 ). Its antioxidant activity has been tested to reduce ferric iron in the ferric reducing antioxidant power (FRAP) assay, and it has been suggested that its catechol structure conveys the antioxidant effect in plasma and in erythrocytes (PMID: 11768243 ). 3,4-Dihydroxyhydrocinnamic acid is a microbial metabolite found in Bifidobacterium, Escherichia, Lactobacillus, and Clostridium (PMID: 28393285 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f92006ab4b0>


  Mrv1652306131921432D          

 13 13  0  0  0  0            999 V2000
   -1.6292   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436   -0.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -0.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3438   -1.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -0.0902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -1.7401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9148   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003   -0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141    0.7349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286   -0.5025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f92006ab4b0>

HMDB0000423
     RDKit          3D
3,4-Dihydroxyhydrocinnamic acid
 23 23  0  0  0  0  0  0  0  0999 V2000
   -3.7667   -0.2806   -1.9303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5150   -0.3761   -0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5635   -0.6023    0.1713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1562   -0.2628   -0.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1141   -0.0169   -1.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1956    0.0792   -0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6073    1.3205   -0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8222    1.4285    0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6139    0.3055    0.7604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8413    0.3984    1.4041 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1966   -0.9374    0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0064   -2.0440    0.5514 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9894   -1.0262   -0.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6355   -0.1110    1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1244    0.6039    0.5623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8905   -1.2223    0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2776    0.9426   -1.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1315   -0.8772   -1.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0099    2.2132   -0.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1787    2.3975    0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1856    1.3034    1.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8796   -1.9636    1.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6686   -2.0024   -0.6365 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  1  0
 11 13  2  0
 13  6  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  7 19  1  0
  8 20  1  0
 10 21  1  0
 12 22  1  0
 13 23  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f92006ab4b0>


  Mrv1652306131921432D          

 13 13  0  0  0  0            999 V2000
   -1.6292   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436   -0.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -0.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3438   -1.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -0.0902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -1.7401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9148   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003   -0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141    0.7349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286   -0.5025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000516

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)

> <INCHI_KEY>
DZAUWHJDUNRCTF-UHFFFAOYSA-N

> <FORMULA>
C9H10O4

> <MOLECULAR_WEIGHT>
182.1733

> <EXACT_MASS>
182.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.848789876051534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(3,4-dihydroxyphenyl)propanoic acid

> <ALOGPS_LOGP>
1.04

> <JCHEM_LOGP>
1.448432127

> <ALOGPS_LOGS>
-1.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.290319681157882

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8379150142223004

> <JCHEM_PKA_STRONGEST_BASIC>
-6.28908665826041

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
45.9284

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.62e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydrocaffeic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f92006ab4b0>

HMDB0000423
     RDKit          3D
3,4-Dihydroxyhydrocinnamic acid
 23 23  0  0  0  0  0  0  0  0999 V2000
   -3.7667   -0.2806   -1.9303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5150   -0.3761   -0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5635   -0.6023    0.1713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1562   -0.2628   -0.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1141   -0.0169   -1.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1956    0.0792   -0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6073    1.3205   -0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8222    1.4285    0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6139    0.3055    0.7604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8413    0.3984    1.4041 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1966   -0.9374    0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0064   -2.0440    0.5514 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9894   -1.0262   -0.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6355   -0.1110    1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1244    0.6039    0.5623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8905   -1.2223    0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2776    0.9426   -1.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1315   -0.8772   -1.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0099    2.2132   -0.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1787    2.3975    0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1856    1.3034    1.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8796   -1.9636    1.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6686   -2.0024   -0.6365 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  1  0
 11 13  2  0
 13  6  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  7 19  1  0
  8 20  1  0
 10 21  1  0
 12 22  1  0
 13 23  1  0
M  END
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PDB for #<Metabolite:0x00007f92006ab4b0>

HEADER    PROTEIN                                 13-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUN-19         0                                  
HETATM    1  C   UNK     0      -3.041  -0.938   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.375  -0.168   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.709  -0.938   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.709  -2.478   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.375  -3.248   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.041  -2.478   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.042  -0.168   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -7.042  -3.248   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.708  -0.168   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.374  -0.938   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.960  -0.168   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.960   1.372   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.293  -0.938   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    3                                                            
CONECT    8    4                                                            
CONECT    9    1   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for #<Metabolite:0x00007f92006ab4b0>

COMPND    HMDB0000423
HETATM    1  O1  UNL     1      -3.767  -0.281  -1.930  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.515  -0.376  -0.708  1.00  0.00           C  
HETATM    3  O2  UNL     1      -4.564  -0.602   0.171  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.156  -0.263  -0.126  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.114  -0.017  -1.202  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.196   0.079  -0.515  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.607   1.320  -0.089  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.822   1.428   0.551  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.614   0.305   0.760  1.00  0.00           C  
HETATM   10  O3  UNL     1       3.841   0.398   1.404  1.00  0.00           O  
HETATM   11  C8  UNL     1       2.197  -0.937   0.330  1.00  0.00           C  
HETATM   12  O4  UNL     1       3.006  -2.044   0.551  1.00  0.00           O  
HETATM   13  C9  UNL     1       0.989  -1.026  -0.302  1.00  0.00           C  
HETATM   14  H1  UNL     1      -4.636  -0.111   1.071  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.124   0.604   0.562  1.00  0.00           H  
HETATM   16  H3  UNL     1      -1.891  -1.222   0.362  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.278   0.943  -1.732  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.131  -0.877  -1.927  1.00  0.00           H  
HETATM   19  H6  UNL     1      -0.010   2.213  -0.248  1.00  0.00           H  
HETATM   20  H7  UNL     1       2.179   2.397   0.903  1.00  0.00           H  
HETATM   21  H8  UNL     1       4.186   1.303   1.738  1.00  0.00           H  
HETATM   22  H9  UNL     1       3.880  -1.964   1.012  1.00  0.00           H  
HETATM   23  H10 UNL     1       0.669  -2.002  -0.636  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5   15   16
CONECT    5    6   17   18
CONECT    6    7    7   13
CONECT    7    8   19
CONECT    8    9    9   20
CONECT    9   10   11
CONECT   10   21
CONECT   11   12   13   13
CONECT   12   22
CONECT   13   23
END
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SMILES for #<Metabolite:0x00007f92006ab4b0>

OC(=O)CCC1=CC(O)=C(O)C=C1
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INCHI for #<Metabolite:0x00007f92006ab4b0>

InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)
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Synonyms
ValueSource
3,4-Dihydroxy-beta-phenylpropionic acidChEBI
3,4-Dihydroxybenzenepropionic acidChEBI
3,4-Dihydroxydihydrocinnamic acidChEBI
3,4-Dihydroxyphenylpropionic acidChEBI
3-(3,4-Dihydroxyphenyl)propanoateKegg
3,4-Dihydroxy-b-phenylpropionateGenerator
3,4-Dihydroxy-b-phenylpropionic acidGenerator
3,4-Dihydroxy-beta-phenylpropionateGenerator
3,4-Dihydroxy-β-phenylpropionateGenerator
3,4-Dihydroxy-β-phenylpropionic acidGenerator
3,4-DihydroxybenzenepropanoateGenerator
3,4-DihydroxybenzenepropionateGenerator
3,4-DihydroxydihydrocinnamateGenerator
3,4-DihydroxyphenylpropionateGenerator
3-(3,4-Dihydroxyphenyl)propionateGenerator
DihydrocaffeateGenerator
HydrocaffeateGenerator
3-(3,4-Dihydroxyphenyl)propanoic acidGenerator
3,4-DihydroxyhydrocinnamateGenerator
3,4-Dihydroxy-(6ci,7ci,8ci)hydrocinnamateHMDB
3,4-Dihydroxy-(6ci,7ci,8ci)hydrocinnamic acidHMDB
3,4-Dihydroxyphenylpropionic acid, potassium saltHMDB
DHCHMDB
3,4-Dihydroxyhydrocinnamic acidHMDB
3-(3',4'-Dihydroxyphenyl)propanoic acidHMDB
Molecular FormulaC9H10O4
Average Mass182.1733
Monoisotopic Mass182.057908808
IUPAC Name3-(3,4-dihydroxyphenyl)propanoic acid
Traditional Namedihydrocaffeic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CCC1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)
InChI KeyDZAUWHJDUNRCTF-UHFFFAOYSA-N