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Showing metabocard for 4-O-Methylgallic acid (HMDB0013198)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-11-30 15:50:49 UTC
Update Date2023-02-21 17:17:56 UTC
HMDB IDHMDB0013198
Secondary Accession Numbers
  • HMDB13198
Metabolite Identification
Common Name4-O-Methylgallic acid
Description4-O-Methyl gallic acid (4-OMGA) has first been identified as a major methyl derivative of gallic acid in human plasma and urine. More recently, 4-O-methyl gallic acid (4-OMGA) has been found in urine during regular black tea ingestion and in plasma after moderate red wine consumption. PMID: 15527792 . 4-O-methylgallic acid (4-OMGA), a major metabolite of gallic acid abundant in red wine. 4-OMGA inhibited the expression of intercellular adhesion molecule-1(ICAM-1) and vascular cell adhesion molecule-1 (VCAM-1) in human umbilical vein endothelial cells (HUVECs) stimulated with tumor necrosis factor-alpha (TNF-alpha), resulting in the suppression of leukocyte adhesion to HUVECs (PMID: 17027748 ). 4-O-Methyl gallic acid has been found to be a metabolite of Beauveria and Pantoea (PMID: 17111140 ) (https://www.researchgate.net/publication/275561863_Microbial_Degradation_of_Bergenin_a_Phenolic_C-Glucoside).
Structure
Data?1676999876
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0013198 (4-O-Methylgallic acid)


  Mrv1652303102016502D          

 13 13  0  0  0  0            999 V2000
    3.5220    1.9058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    1.0808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.0808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.8068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.8068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    2.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1 13  1  0  0  0  0
  2  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4 12  1  0  0  0  0
  5 12  2  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
  7 10  2  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
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3D MOL for HMDB0013198 (4-O-Methylgallic acid)

HMDB0013198
     RDKit          3D
4-O-Methylgallic acid
 21 21  0  0  0  0  0  0  0  0999 V2000
   -3.1781    0.9630    0.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2802    0.5710   -0.5934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9762    0.2231   -0.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6574   -1.1095   -0.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6557   -2.0572   -0.1093 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6668   -1.4673    0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6780   -0.5357   -0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0805   -0.8902    0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3638   -2.0839    0.3395 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0853    0.0356    0.0577 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3536    0.8021   -0.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0164    1.1730   -0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3353    2.4881   -0.7340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0605    2.0196    0.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2111    0.8943   -0.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1385    0.2924    1.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4153   -3.0237    0.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8874   -2.5039    0.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9535   -0.0808   -0.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1285    1.5549   -0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3054    2.7352   -0.8602 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 12  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  6 18  1  0
 10 19  1  0
 11 20  1  0
 13 21  1  0
M  END
Download

3D SDF for HMDB0013198 (4-O-Methylgallic acid)


  Mrv1652303102016502D          

 13 13  0  0  0  0            999 V2000
    3.5220    1.9058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    1.0808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.0808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.8068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.8068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    2.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1 13  1  0  0  0  0
  2  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4 12  1  0  0  0  0
  5 12  2  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
  7 10  2  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013198

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C(C=C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O5/c1-13-7-5(9)2-4(8(11)12)3-6(7)10/h2-3,9-10H,1H3,(H,11,12)

> <INCHI_KEY>
UBXDWYFLYYJQFR-UHFFFAOYSA-N

> <FORMULA>
C8H8O5

> <MOLECULAR_WEIGHT>
184.1461

> <EXACT_MASS>
184.037173366

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.722098608495433

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5-dihydroxy-4-methoxybenzoic acid

> <ALOGPS_LOGP>
1.32

> <JCHEM_LOGP>
0.8660268150000002

> <ALOGPS_LOGS>
-1.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.766838011092101

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9282695444090763

> <JCHEM_PKA_STRONGEST_BASIC>
-4.857231269035329

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
43.7392

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.93e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5-dihydroxy-4-methoxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0013198 (4-O-Methylgallic acid)

HMDB0013198
     RDKit          3D
4-O-Methylgallic acid
 21 21  0  0  0  0  0  0  0  0999 V2000
   -3.1781    0.9630    0.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2802    0.5710   -0.5934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9762    0.2231   -0.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6574   -1.1095   -0.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6557   -2.0572   -0.1093 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6668   -1.4673    0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6780   -0.5357   -0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0805   -0.8902    0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3638   -2.0839    0.3395 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0853    0.0356    0.0577 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3536    0.8021   -0.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0164    1.1730   -0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3353    2.4881   -0.7340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0605    2.0196    0.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2111    0.8943   -0.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1385    0.2924    1.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4153   -3.0237    0.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8874   -2.5039    0.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9535   -0.0808   -0.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1285    1.5549   -0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3054    2.7352   -0.8602 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 12  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  6 18  1  0
 10 19  1  0
 11 20  1  0
 13 21  1  0
M  END
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PDB for HMDB0013198 (4-O-Methylgallic acid)

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  O   UNK     0       6.574   3.557   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.907   2.017   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.242   2.017   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.241  -3.373   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.908  -3.373   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.574   2.017   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.574  -1.063   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.241   1.247   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.908   1.247   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.241  -0.293   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.908  -0.293   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.574  -2.603   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.908   4.327   0.000  0.00  0.00           C+0
CONECT    1    6   13                                                       
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4   12                                                            
CONECT    5   12                                                            
CONECT    6    1    8    9                                                  
CONECT    7   10   11   12                                                  
CONECT    8    2    6   10                                                  
CONECT    9    3    6   11                                                  
CONECT   10    7    8                                                       
CONECT   11    7    9                                                       
CONECT   12    4    5    7                                                  
CONECT   13    1                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for HMDB0013198 (4-O-Methylgallic acid)

COMPND    HMDB0013198
HETATM    1  C1  UNL     1      -3.178   0.963   0.394  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.280   0.571  -0.593  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.976   0.223  -0.421  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.657  -1.109  -0.176  1.00  0.00           C  
HETATM    5  O2  UNL     1      -1.656  -2.057  -0.109  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.667  -1.467   0.000  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.678  -0.536  -0.062  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.081  -0.890   0.120  1.00  0.00           C  
HETATM    9  O3  UNL     1       3.364  -2.084   0.339  1.00  0.00           O  
HETATM   10  O4  UNL     1       4.085   0.036   0.058  1.00  0.00           O  
HETATM   11  C7  UNL     1       1.354   0.802  -0.309  1.00  0.00           C  
HETATM   12  C8  UNL     1       0.016   1.173  -0.488  1.00  0.00           C  
HETATM   13  O5  UNL     1      -0.335   2.488  -0.734  1.00  0.00           O  
HETATM   14  H1  UNL     1      -3.061   2.020   0.712  1.00  0.00           H  
HETATM   15  H2  UNL     1      -4.211   0.894  -0.033  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.138   0.292   1.270  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.415  -3.024   0.070  1.00  0.00           H  
HETATM   18  H5  UNL     1       0.887  -2.504   0.189  1.00  0.00           H  
HETATM   19  H6  UNL     1       4.953  -0.081  -0.459  1.00  0.00           H  
HETATM   20  H7  UNL     1       2.128   1.555  -0.364  1.00  0.00           H  
HETATM   21  H8  UNL     1      -1.305   2.735  -0.860  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3
CONECT    3    4    4   12
CONECT    4    5    6
CONECT    5   17
CONECT    6    7    7   18
CONECT    7    8   11
CONECT    8    9    9   10
CONECT   10   19
CONECT   11   12   12   20
CONECT   12   13
CONECT   13   21
END
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SMILES for HMDB0013198 (4-O-Methylgallic acid)

COC1=C(O)C=C(C=C1O)C(O)=O
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INCHI for HMDB0013198 (4-O-Methylgallic acid)

InChI=1S/C8H8O5/c1-13-7-5(9)2-4(8(11)12)3-6(7)10/h2-3,9-10H,1H3,(H,11,12)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
4-O-MethylgallateGenerator
3,5-Dihydroxy-4-methoxybenzoic acidMeSH
4-Methoxy-3,5-dihydroxybenzoic acidMeSH
4-Methoxygallic acidMeSH
4OMGA CPDMeSH
4-MethoxygallateGenerator, HMDB
3,5-Dihydroxy-4-methoxy-benzoateHMDB
3,5-Dihydroxy-4-methoxy-benzoic acidHMDB
3,5-Dihydroxy-4-methoxybenzoateHMDB, Generator
3,5-Dihydroxy-P-anisic acidHMDB
4-Methoxy-3,5-dihydroxybenzoateHMDB
5-Hydroxyisovanillic acidHMDB
4-O-Methylgallic acidMeSH
Chemical FormulaC8H8O5
Average Molecular Weight184.1461
Monoisotopic Molecular Weight184.037173366
IUPAC Name3,5-dihydroxy-4-methoxybenzoic acid
Traditional Name3,5-dihydroxy-4-methoxybenzoic acid
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=C(C=C1O)C(O)=O
InChI Identifier
InChI=1S/C8H8O5/c1-13-7-5(9)2-4(8(11)12)3-6(7)10/h2-3,9-10H,1H3,(H,11,12)
InChI KeyUBXDWYFLYYJQFR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentGallic acid and derivatives
Alternative Parents
Substituents
  • Gallic acid or derivatives
  • P-methoxybenzoic acid or derivatives
  • Methoxyphenol
  • Benzoic acid
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Resorcinol
  • Phenol ether
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.93 g/LALOGPS
logP1.32ALOGPS
logP0.87ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.93ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.74 m³·mol⁻¹ChemAxon
Polarizability16.72 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]+142.86531661259
DarkChem[M-H]-139.93331661259
DeepCCS[M+H]+136.05930932474
DeepCCS[M-H]-132.23230932474
DeepCCS[M-2H]-169.47330932474
DeepCCS[M+Na]+145.01230932474
AllCCS[M+H]+139.632859911
AllCCS[M+H-H2O]+135.332859911
AllCCS[M+NH4]+143.532859911
AllCCS[M+Na]+144.632859911
AllCCS[M-H]-135.532859911
AllCCS[M+Na-2H]-136.332859911
AllCCS[M+HCOO]-137.232859911

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, 2022.2.59 minutes32390414
Predicted by Siyang on May 30, 202210.1076 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.19 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid86.7 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid998.6 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid308.7 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid78.6 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid165.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid61.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid360.1 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 Acid327.5 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)207.4 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid677.8 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid193.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid965.9 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid202.0 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid290.5 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate588.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA258.9 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water325.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-O-Methylgallic acidCOC1=C(O)C=C(C=C1O)C(O)=O3032.5Standard polar33892256
4-O-Methylgallic acidCOC1=C(O)C=C(C=C1O)C(O)=O1740.0Standard non polar33892256
4-O-Methylgallic acidCOC1=C(O)C=C(C=C1O)C(O)=O1616.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-O-Methylgallic acid,1TMS,isomer #1COC1=C(O)C=C(C(=O)O)C=C1O[Si](C)(C)C1814.0Semi standard non polar33892256
4-O-Methylgallic acid,1TMS,isomer #2COC1=C(O)C=C(C(=O)O[Si](C)(C)C)C=C1O1842.7Semi standard non polar33892256
4-O-Methylgallic acid,2TMS,isomer #1COC1=C(O[Si](C)(C)C)C=C(C(=O)O)C=C1O[Si](C)(C)C1845.1Semi standard non polar33892256
4-O-Methylgallic acid,2TMS,isomer #2COC1=C(O)C=C(C(=O)O[Si](C)(C)C)C=C1O[Si](C)(C)C1835.2Semi standard non polar33892256
4-O-Methylgallic acid,3TMS,isomer #1COC1=C(O[Si](C)(C)C)C=C(C(=O)O[Si](C)(C)C)C=C1O[Si](C)(C)C1882.9Semi standard non polar33892256
4-O-Methylgallic acid,1TBDMS,isomer #1COC1=C(O)C=C(C(=O)O)C=C1O[Si](C)(C)C(C)(C)C2119.9Semi standard non polar33892256
4-O-Methylgallic acid,1TBDMS,isomer #2COC1=C(O)C=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C1O2126.6Semi standard non polar33892256
4-O-Methylgallic acid,2TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=C(C(=O)O)C=C1O[Si](C)(C)C(C)(C)C2383.3Semi standard non polar33892256
4-O-Methylgallic acid,2TBDMS,isomer #2COC1=C(O)C=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2339.8Semi standard non polar33892256
4-O-Methylgallic acid,3TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2570.9Semi 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 and Quantified0.084 +/- 0.063 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.02 +/- 0.002 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.023 +/- 0.002 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.025 +/- 0.002 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.057 +/- 0.017 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.05 +/- 0.015 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.029 +/- 0.006 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.04 +/- 0.014 uMAdult (>18 years old)Male
Normal		 details
FecesDetected and Quantified6.245 +/- 0.326 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified6.734 +/- 0.706 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.74 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.407 +/- 0.680 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.440 +/- 0.680 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.22666 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.229 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.211 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.153 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.29333 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 923 details
UrineDetected and Quantified0.017 +/- 0.003 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
UrineDetected and Quantified0.008 +/- 0.002 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
UrineDetected and Quantified0.014 +/- 0.004 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 923 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 923 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001960
KNApSAcK IDNot Available
Chemspider ID70398
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound78016
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Oliveira MV, Badia E, Carbonneau MA, Grimaldi P, Fouret G, Lauret C, Leger CL: Potential anti-atherogenic cell action of the naturally occurring 4-O-methyl derivative of gallic acid on Ang II-treated macrophages. FEBS Lett. 2004 Nov 5;577(1-2):239-44. [PubMed:15527792 ]
  2. Lee G, Na HJ, Namkoong S, Jeong Kwon H, Han S, Ha KS, Kwon YG, Lee H, Kim YM: 4-O-methylgallic acid down-regulates endothelial adhesion molecule expression by inhibiting NF-kappaB-DNA-binding activity. Eur J Pharmacol. 2006 Dec 3;551(1-3):143-51. Epub 2006 Sep 8. [PubMed:17027748 ]
  3. Hsu FL, Yang LM, Chang SF, Wang LH, Hsu CY, Liu PC, Lin SJ: Biotransformation of gallic acid by Beauveria sulfurescens ATCC 7159. Appl Microbiol Biotechnol. 2007 Mar;74(3):659-66. doi: 10.1007/s00253-006-0692-z. Epub 2006 Nov 17. [PubMed:17111140 ]