Showing metabocard for Dihydroferulic acid (MMDBc0000693)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:52:53 UTC
Update Date2024-04-30 19:33:33 UTC
Metabolite IDMMDBc0000693
Metabolite Identification
Common NameDihydroferulic acid
DescriptionDihydroferulic acid, also known as 3-(4-hydroxy-3-methoxyphenyl)propionic acid or dihydroconiferylate, is classified as a member of the phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Dihydroferulic acid is considered to be slightly soluble (in water) and acidic. Dihydroferulic acid is a phenolic acid metabolite and was found to be significantly elevated in serum after whole grain consumption which makes this compound a potential serum biomarker of whole grain intake (PMID: 25646321 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f91fd1d7568>


  Mrv1652309272007472D          

 14 14  0  0  0  0            999 V2000
10017.751910017.8102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10020.611110019.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.325110019.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.041210019.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.755310019.0478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10022.041210020.2858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10019.896910019.0476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.182510019.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.467910019.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.467910018.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.182310017.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.896910018.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.182210016.9835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10019.898110016.5701    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
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f91fd1d7568>

HMDB0062121
     RDKit          3D
Dihydroferulic acid
 26 26  0  0  0  0  0  0  0  0999 V2000
    2.9708    1.9888   -0.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9831    0.6653   -0.7181 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8519   -0.1388   -0.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6810    0.3680   -0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4477   -0.4180   -0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7017    0.1270    0.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9155   -0.0561    1.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2257    0.5478    2.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6436    0.5253    3.3330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0231    1.1463    1.1952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3483   -1.7119   -0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8505   -2.2190   -1.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797   -1.4332   -1.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2051   -1.8858   -1.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0991    2.5779   -0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9714    2.0532    0.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8694    2.5075   -0.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6178    1.4057    0.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7751    1.2376    0.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5328   -0.3124   -0.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1226    0.4727    2.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9251   -1.1109    2.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3812    2.0953    1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2368   -2.3472   -0.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9255   -3.2474   -1.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2742   -2.8377   -1.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13  3  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 14 26  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f91fd1d7568>


  Mrv1652309272007472D          

 14 14  0  0  0  0            999 V2000
10017.751910017.8102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10020.611110019.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.325110019.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.041210019.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.755310019.0478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10022.041210020.2858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10019.896910019.0476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.182510019.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.467910019.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.467910018.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.182310017.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.896910018.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.182210016.9835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10019.898110016.5701    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
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000693

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=CC(CCC(O)=O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2,4,6,11H,3,5H2,1H3,(H,12,13)

> <INCHI_KEY>
BOLQJTPHPSDZHR-UHFFFAOYSA-N

> <FORMULA>
C10H12O4

> <MOLECULAR_WEIGHT>
196.1999

> <EXACT_MASS>
196.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.802083951346205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-hydroxy-3-methoxyphenyl)propanoic acid

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
1.5943261829999997

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.946560494761734

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9524008986487043

> <JCHEM_PKA_STRONGEST_BASIC>
-4.892121858205717

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
50.410700000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
homovanillinic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f91fd1d7568>

HMDB0062121
     RDKit          3D
Dihydroferulic acid
 26 26  0  0  0  0  0  0  0  0999 V2000
    2.9708    1.9888   -0.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9831    0.6653   -0.7181 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8519   -0.1388   -0.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6810    0.3680   -0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4477   -0.4180   -0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7017    0.1270    0.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9155   -0.0561    1.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2257    0.5478    2.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6436    0.5253    3.3330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0231    1.1463    1.1952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3483   -1.7119   -0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8505   -2.2190   -1.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797   -1.4332   -1.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2051   -1.8858   -1.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0991    2.5779   -0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9714    2.0532    0.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8694    2.5075   -0.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6178    1.4057    0.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7751    1.2376    0.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5328   -0.3124   -0.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1226    0.4727    2.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9251   -1.1109    2.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3812    2.0953    1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2368   -2.3472   -0.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9255   -3.2474   -1.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2742   -2.8377   -1.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13  3  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 14 26  1  0
M  END
Download

PDB for #<Metabolite:0x00007f91fd1d7568>

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    8699.8038699.912   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8705.1418702.993   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8706.4738702.223   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8707.8108702.993   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8709.1438702.223   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8707.8108704.534   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8703.8088702.222   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8702.4748702.992   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8701.1408702.222   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8701.1408700.682   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8702.4748699.912   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8703.8088700.682   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8702.4748698.369   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8703.8108697.598   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   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END
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3D PDB for #<Metabolite:0x00007f91fd1d7568>

COMPND    HMDB0062121
HETATM    1  C1  UNL     1       2.971   1.989  -0.275  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.983   0.665  -0.718  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.852  -0.139  -0.693  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.681   0.368  -0.222  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.448  -0.418  -0.191  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.702   0.127   0.314  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.916  -0.056   1.786  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.226   0.548   2.140  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.644   0.525   3.333  1.00  0.00           O  
HETATM   10  O3  UNL     1      -4.023   1.146   1.195  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.348  -1.712  -0.646  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.851  -2.219  -1.125  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.980  -1.433  -1.156  1.00  0.00           C  
HETATM   14  O4  UNL     1       3.205  -1.886  -1.623  1.00  0.00           O  
HETATM   15  H1  UNL     1       2.099   2.578  -0.631  1.00  0.00           H  
HETATM   16  H2  UNL     1       2.971   2.053   0.844  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.869   2.508  -0.663  1.00  0.00           H  
HETATM   18  H4  UNL     1       0.618   1.406   0.139  1.00  0.00           H  
HETATM   19  H5  UNL     1      -1.775   1.238   0.122  1.00  0.00           H  
HETATM   20  H6  UNL     1      -2.533  -0.312  -0.276  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.123   0.473   2.352  1.00  0.00           H  
HETATM   22  H8  UNL     1      -1.925  -1.111   2.105  1.00  0.00           H  
HETATM   23  H9  UNL     1      -4.381   2.095   1.252  1.00  0.00           H  
HETATM   24  H10 UNL     1      -1.237  -2.347  -0.628  1.00  0.00           H  
HETATM   25  H11 UNL     1       0.925  -3.247  -1.485  1.00  0.00           H  
HETATM   26  H12 UNL     1       3.274  -2.838  -1.957  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   18
CONECT    5    6   11   11
CONECT    6    7   19   20
CONECT    7    8   21   22
CONECT    8    9    9   10
CONECT   10   23
CONECT   11   12   24
CONECT   12   13   13   25
CONECT   13   14
CONECT   14   26
END
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SMILES for #<Metabolite:0x00007f91fd1d7568>

COC1=CC(CCC(O)=O)=CC=C1O
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INCHI for #<Metabolite:0x00007f91fd1d7568>

InChI=1S/C10H12O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2,4,6,11H,3,5H2,1H3,(H,12,13)
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Synonyms
ValueSource
Dihydroconiferylic acidChEBI
3-(4-Hydroxy-3-methoxyphenyl)propionateGenerator
DihydroconiferylateGenerator
DihydroferulateGenerator
HydroferulateHMDB
(4-Hydroxy-3-methoxyphenyl)propionic acidHMDB
3-(3'-Methoxy-4'-hydroxyphenyl)propionic acidHMDB
3-(3-Methoxy-4-hydroxyphenyl)propanoic acidHMDB
3-(3-Methoxy-4-hydroxyphenyl)propionic acidHMDB
3-(3’-methoxy-4’-hydroxyphenyl)propionic acidHMDB
3-(4-Hydroxy-3-methoxyphenyl)propanoic acidHMDB
3-Methoxy-4-hydroxyphenylpropionic acidHMDB
3-Methoxyphloretic acidHMDB
4-Hydroxy-3-methoxybenzenepropanoic acidHMDB
DHFAHMDB
Shorbic acidHMDB
beta-(4-Hydroxy-3-methoxyphenyl)propionic acidHMDB
beta-3-Methoxy-4-hydroxyphenylpropionic acidHMDB
Β-(4-hydroxy-3-methoxyphenyl)propionic acidHMDB
Β-3-methoxy-4-hydroxyphenylpropionic acidHMDB
3-(4'-Hydroxy-3'-methoxyphenyl)propanoic acidHMDB
4-Hydroxy-3-methoxyhydrocinnamic acidPhytoBank
4-Hydroxy-3-methoxybenzenepropionic acidPhytoBank
(4-Hydroxy-3-methoxyphenyl)propanoic acidPhytoBank
3-(3'-Methoxy-4'-hydroxyphenyl)propanoic acidPhytoBank
3-(3’-Methoxy-4’-hydroxyphenyl)propanoic acidPhytoBank
3-Methoxy-4-hydroxyphenylpropanoic acidPhytoBank
alpha,beta-Dihydroferulic acidPhytoBank
α,β-Dihydroferulic acidPhytoBank
beta-(4-Hydroxy-3-methoxyphenyl)propanoic acidPhytoBank
β-(4-Hydroxy-3-methoxyphenyl)propanoic acidPhytoBank
beta-3-Methoxy-4-hydroxyphenylpropanoic acidPhytoBank
β-3-Methoxy-4-hydroxyphenylpropanoic acidPhytoBank
3-(4-Hydroxy-3-methoxyphenyl) propanoic acidHMDB
Molecular FormulaC10H12O4
Average Mass196.1999
Monoisotopic Mass196.073558872
IUPAC Name3-(4-hydroxy-3-methoxyphenyl)propanoic acid
Traditional Namehomovanillinic acid
CAS Registry NumberNot Available
SMILES
COC1=CC(CCC(O)=O)=CC=C1O
InChI Identifier
InChI=1S/C10H12O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2,4,6,11H,3,5H2,1H3,(H,12,13)
InChI KeyBOLQJTPHPSDZHR-UHFFFAOYSA-N