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Showing metabocard for Gallic acid (HMDB0005807)

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enzymes (3) Show 3 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-01-23 13:04:37 UTC
Update Date2023-02-21 17:17:08 UTC
HMDB IDHMDB0005807
Secondary Accession Numbers
  • HMDB05807
Metabolite Identification
Common NameGallic acid
DescriptionGallic acid, also known as gallate or acid, gallic, belongs to the class of organic compounds known as gallic acids. These are organic compounds that contain a 3,4,5-trihydroxybenzoic acid moiety. Gallic acid exists in all living species, ranging from bacteria to plants to humans. Gallic acid is found, on average, in the highest concentration within a few different foods, such as mangos (Mangifera indica), pomegranates (Punica granatum), and cloves (Syzygium aromaticum) and in a lower concentration in green bell peppers (Capsicum annuum), apples (Malus pumila), and carrots (Daucus carota ssp. sativus). Gallic acid has also been detected, but not quantified in, several different foods, such as avocados (Persea americana), natal plums (Carissa macrocarpa), peppermints (Mentha X piperita), loquats (Eriobotrya japonica), and sourdocks (Rumex articus). This could make gallic acid a potential biomarker for the consumption of these foods. Gallic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Gallic acid.
Structure
Data?1676999828
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0005807 (Gallic acid)


  Mrv1652309272007342D          

 12 12  0  0  0  0            999 V2000
   -1.5511   -1.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655   -1.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9801   -1.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9801   -2.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2656   -2.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5511   -2.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6945   -1.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6946   -2.6999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2656   -3.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8366   -1.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8367   -0.2249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1221   -1.4623    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 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
M  END
Download

3D MOL for HMDB0005807 (Gallic acid)

HMDB0005807
     RDKit          3D
Gallic acid
 18 18  0  0  0  0  0  0  0  0999 V2000
    3.0265   -1.4210   -0.6096 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5363   -0.3808   -0.1041 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4289    0.5390    0.4173 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0869   -0.1712   -0.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2074   -1.0955   -0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1700   -0.9143   -0.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0317   -1.8599   -1.1180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7080    0.2244   -0.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0798    0.4103   -0.0134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8491    1.1574    0.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4162    2.2988    1.0475 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5289    0.9644    0.4728 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7754    0.5373    1.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6298   -1.9930   -1.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6514   -2.7053   -1.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6843   -0.2971   -0.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8104    2.9973    1.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1808    1.7091    0.8909 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12  4  1  0
  3 13  1  0
  5 14  1  0
  7 15  1  0
  9 16  1  0
 11 17  1  0
 12 18  1  0
M  END
Download

3D SDF for HMDB0005807 (Gallic acid)


  Mrv1652309272007342D          

 12 12  0  0  0  0            999 V2000
   -1.5511   -1.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655   -1.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9801   -1.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9801   -2.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2656   -2.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5511   -2.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6945   -1.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6946   -2.6999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2656   -3.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8366   -1.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8367   -0.2249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1221   -1.4623    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 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005807

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)

> <INCHI_KEY>
LNTHITQWFMADLM-UHFFFAOYSA-N

> <FORMULA>
C7H6O5

> <MOLECULAR_WEIGHT>
170.12

> <EXACT_MASS>
170.021523293

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.74977776338232

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4,5-trihydroxybenzoic acid

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
0.720132759

> <ALOGPS_LOGS>
-1.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.044962714429534

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9415641190048674

> <JCHEM_PKA_STRONGEST_BASIC>
-6.048647901640675

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
39.2569

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.94e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
galop

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0005807 (Gallic acid)

HMDB0005807
     RDKit          3D
Gallic acid
 18 18  0  0  0  0  0  0  0  0999 V2000
    3.0265   -1.4210   -0.6096 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5363   -0.3808   -0.1041 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4289    0.5390    0.4173 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0869   -0.1712   -0.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2074   -1.0955   -0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1700   -0.9143   -0.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0317   -1.8599   -1.1180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7080    0.2244   -0.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0798    0.4103   -0.0134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8491    1.1574    0.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4162    2.2988    1.0475 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5289    0.9644    0.4728 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7754    0.5373    1.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6298   -1.9930   -1.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6514   -2.7053   -1.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6843   -0.2971   -0.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8104    2.9973    1.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1808    1.7091    0.8909 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12  4  1  0
  3 13  1  0
  5 14  1  0
  7 15  1  0
  9 16  1  0
 11 17  1  0
 12 18  1  0
M  END
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PDB for HMDB0005807 (Gallic acid)

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  C   UNK     0      -2.895  -2.730   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.229  -1.960   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.563  -2.730   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.563  -4.270   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.229  -5.040   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.895  -4.270   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.896  -1.960   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -6.897  -5.040   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -4.229  -6.580   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.562  -1.960   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.562  -0.420   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.228  -2.730   0.000  0.00  0.00           O+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1                                                       
CONECT    7    3                                                            
CONECT    8    4                                                            
CONECT    9    5                                                            
CONECT   10    1   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0005807 (Gallic acid)

COMPND    HMDB0005807
HETATM    1  O1  UNL     1       3.027  -1.421  -0.610  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.536  -0.381  -0.104  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.429   0.539   0.417  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.087  -0.171  -0.078  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.207  -1.096  -0.601  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.170  -0.914  -0.585  1.00  0.00           C  
HETATM    7  O3  UNL     1      -2.032  -1.860  -1.118  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.708   0.224  -0.032  1.00  0.00           C  
HETATM    9  O4  UNL     1      -3.080   0.410  -0.013  1.00  0.00           O  
HETATM   10  C6  UNL     1      -0.849   1.157   0.494  1.00  0.00           C  
HETATM   11  O5  UNL     1      -1.416   2.299   1.048  1.00  0.00           O  
HETATM   12  C7  UNL     1       0.529   0.964   0.473  1.00  0.00           C  
HETATM   13  H1  UNL     1       3.775   0.537   1.355  1.00  0.00           H  
HETATM   14  H2  UNL     1       0.630  -1.993  -1.037  1.00  0.00           H  
HETATM   15  H3  UNL     1      -1.651  -2.705  -1.530  1.00  0.00           H  
HETATM   16  H4  UNL     1      -3.684  -0.297  -0.410  1.00  0.00           H  
HETATM   17  H5  UNL     1      -0.810   2.997   1.439  1.00  0.00           H  
HETATM   18  H6  UNL     1       1.181   1.709   0.891  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5    5   12
CONECT    5    6   14
CONECT    6    7    8    8
CONECT    7   15
CONECT    8    9   10
CONECT    9   16
CONECT   10   11   12   12
CONECT   11   17
CONECT   12   18
END
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SMILES for HMDB0005807 (Gallic acid)

OC(=O)C1=CC(O)=C(O)C(O)=C1
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INCHI for HMDB0005807 (Gallic acid)

InChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
3,4,5-Trihydroxybenzoic acidChEBI
Pyrogallol-5-carboxylic acidChEBI
3,4,5-TrihydroxybenzoateKegg
Pyrogallol-5-carboxylateGenerator
GallateGenerator
Acid, gallicMeSH
3,4,5-Trihydroxy-benzoateHMDB
3,4,5-Trihydroxy-benzoic acidHMDB
3,4,5-Trihydroxybenzoic acid (acd/name 4.0)HMDB
Gallic acid polymerHMDB
Gallic acid tech.HMDB
GalopHMDB
3,4,5-Hydroxybenzoic acidPhytoBank
Gallic acidHMDB
Chemical FormulaC7H6O5
Average Molecular Weight170.12
Monoisotopic Molecular Weight170.021523293
IUPAC Name3,4,5-trihydroxybenzoic acid
Traditional Namegalop
CAS Registry Number149-91-7
SMILES
OC(=O)C1=CC(O)=C(O)C(O)=C1
InChI Identifier
InChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)
InChI KeyLNTHITQWFMADLM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gallic acids. These are organic compounds that contain a 3,4,5-trihydroxybenzoic acid moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentGallic acids
Alternative Parents
Substituents
  • Gallic acid
  • Benzenetriol
  • Benzoic acid
  • Pyrogallol derivative
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point258 - 265 °CNot Available
Boiling Point501.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility11.9 mg/mL at 20 °CNot Available
LogP0.70HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available130.892http://allccs.zhulab.cn/database/detail?ID=AllCCS00000889
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.94 g/LALOGPS
logP1.17ALOGPS
logP0.72ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.94ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.26 m³·mol⁻¹ChemAxon
Polarizability14.75 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.83631661259
DarkChem[M-H]-132.27431661259
DeepCCS[M+H]+133.97730932474
DeepCCS[M-H]-131.45530932474
DeepCCS[M-2H]-167.35130932474
DeepCCS[M+Na]+142.14830932474
AllCCS[M+H]+136.432859911
AllCCS[M+H-H2O]+132.032859911
AllCCS[M+NH4]+140.432859911
AllCCS[M+Na]+141.632859911
AllCCS[M-H]-129.632859911
AllCCS[M+Na-2H]-130.632859911
AllCCS[M+HCOO]-131.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Gallic acidOC(=O)C1=CC(O)=C(O)C(O)=C13098.5Standard polar33892256
Gallic acidOC(=O)C1=CC(O)=C(O)C(O)=C11677.4Standard non polar33892256
Gallic acidOC(=O)C1=CC(O)=C(O)C(O)=C11591.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Gallic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(O)=C(O)C(O)=C12023.1Semi standard non polar33892256
Gallic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC(C(=O)O)=CC(O)=C1O1918.9Semi standard non polar33892256
Gallic acid,1TMS,isomer #3C[Si](C)(C)OC1=C(O)C=C(C(=O)O)C=C1O1950.8Semi standard non polar33892256
Gallic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(O)=C(O)C(O[Si](C)(C)C)=C11926.7Semi standard non polar33892256
Gallic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC(O)=C(O[Si](C)(C)C)C(O)=C11933.4Semi standard non polar33892256
Gallic acid,2TMS,isomer #3C[Si](C)(C)OC1=CC(C(=O)O)=CC(O[Si](C)(C)C)=C1O1915.7Semi standard non polar33892256
Gallic acid,2TMS,isomer #4C[Si](C)(C)OC1=CC(C(=O)O)=CC(O)=C1O[Si](C)(C)C1882.9Semi standard non polar33892256
Gallic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=C(O)C(O[Si](C)(C)C)=C11978.3Semi standard non polar33892256
Gallic acid,3TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC(O)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11924.2Semi standard non polar33892256
Gallic acid,3TMS,isomer #3C[Si](C)(C)OC1=CC(C(=O)O)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C1906.8Semi standard non polar33892256
Gallic acid,4TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11977.4Semi standard non polar33892256
Gallic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=C(O)C(O)=C12297.1Semi standard non polar33892256
Gallic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(C(=O)O)=CC(O)=C1O2238.0Semi standard non polar33892256
Gallic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C(O)C=C(C(=O)O)C=C1O2253.2Semi standard non polar33892256
Gallic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=C(O)C(O[Si](C)(C)C(C)(C)C)=C12443.9Semi standard non polar33892256
Gallic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O)=C12473.9Semi standard non polar33892256
Gallic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)=C1O2457.6Semi standard non polar33892256
Gallic acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC(C(=O)O)=CC(O)=C1O[Si](C)(C)C(C)(C)C2447.0Semi standard non polar33892256
Gallic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C12647.3Semi standard non polar33892256
Gallic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12625.6Semi standard non polar33892256
Gallic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C2676.8Semi standard non polar33892256
Gallic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12844.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Gallic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001i-0791200000-4d3e1baed2effb0bf15b2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gallic acid GC-MS (4 TMS)splash10-053r-0491700000-68a1d17dd1d0bb6c53542014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gallic acid EI-B (Non-derivatized)splash10-0fk9-5900000000-6b43adb858d50b520ba72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gallic acid GC-EI-TOF (Non-derivatized)splash10-001i-0791200000-4d3e1baed2effb0bf15b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gallic acid GC-MS (Non-derivatized)splash10-053r-0491700000-68a1d17dd1d0bb6c53542017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gallic acid GC-EI-TOF (Non-derivatized)splash10-001i-0691200000-8b11cbd28f656c4426b42017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gallic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fmi-1900000000-56bf9b5e0a68a9c0776a2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gallic acid GC-MS (4 TMS) - 70eV, Positivesplash10-00xu-4009300000-4326897e134d4856b1802017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gallic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gallic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0fk9-2900000000-1949ca7ce1b8b610c2782015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Gallic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0umi-0900000000-e8e6e57cdaf8d518781a2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gallic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a59-9600000000-8b3c3dc9e263c174a0ac2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gallic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0ue9-9000000000-da4704e31ba4de6b3aca2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gallic acid EI-B (HITACHI M-52) , Positive-QTOFsplash10-0fk9-5900000000-425a258abda96a507ea02012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gallic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-014i-0900000000-951aa8106825faaca3f92012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gallic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-004i-0900000000-bdedf4b4b4fd922ec7042012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gallic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-004i-5900000000-46d7a232b169910da4622012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gallic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-004i-9300000000-010429242e38b1b28c132012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gallic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-0g29-9100000000-fb4dc241b26c248950f72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gallic acid DI-ESI-qTof , Positive-QTOFsplash10-0ufr-0900000000-8e1ce790677a7c04e5802017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gallic acid DI-ESI-qTof , Negative-QTOFsplash10-004i-0900000000-8999270f1e2b746047f72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gallic acid LC-ESI-QQ , negative-QTOFsplash10-014i-0900000000-880097b21bcd57ec8f772017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gallic acid LC-ESI-QQ , negative-QTOFsplash10-004i-0900000000-bdedf4b4b4fd922ec7042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gallic acid LC-ESI-QQ , negative-QTOFsplash10-004i-5900000000-bf4cb2a480d9abb570d42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gallic acid LC-ESI-QQ , negative-QTOFsplash10-004i-9300000000-63bfcc112fc600a150de2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gallic acid LC-ESI-QQ , negative-QTOFsplash10-0g29-9100000000-fb4dc241b26c248950f72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gallic acid Linear Ion Trap , negative-QTOFsplash10-00di-0900000000-6a9289e729e66d03cf502017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gallic acid Linear Ion Trap , negative-QTOFsplash10-00di-0900000000-175241488c5f0956df1f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gallic acid , positive-QTOFsplash10-0kor-0900000000-1ceb76e12bc399878e0d2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gallic acid 10V, Positive-QTOFsplash10-00di-0900000000-8e403dcee60bc20ba7b42016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gallic acid 20V, Positive-QTOFsplash10-0fb9-0900000000-20a78444c2179ed7730f2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gallic acid 40V, Positive-QTOFsplash10-00os-9800000000-3011ae50626d9c15fadd2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gallic acid 10V, Negative-QTOFsplash10-014i-0900000000-bceef5d1a34c38d340ed2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gallic acid 20V, Negative-QTOFsplash10-00or-0900000000-bbec391317d064ab4d892016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gallic acid 40V, Negative-QTOFsplash10-00or-8900000000-049b564c5923498a6f3e2016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.008 +/- 0.005 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.003 +/- 0.001 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.01 +/- 0.005 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.007 +/- 0.003 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.002 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.002 +/- 0 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.001 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.005 +/- 0.004 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0-0.058 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified2.09 +/- 0.22 uMAdult (>18 years old)Both
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected and Quantified11.874 +/- 0.353 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified12.0504 +/- 0.0588 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified12.873 +/- 1.411 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified13.873 +/- 4.526 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.0267 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.213 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.107 +/- 0.160 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.110 +/- 0.130 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0533 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.073 +/- 0.06 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.019 +/- 0.052 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.38 +/- 0.092 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0473 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.0617 +/- 0.0740 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.003 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 413 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 413 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 413 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 413 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 413 details
UrineDetected and Quantified0.003 +/- 0.001 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
UrineDetected and Quantified0.006 +/- 0.001 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound ID413
FooDB IDFDB000662
KNApSAcK IDC00002647
Chemspider ID361
KEGG Compound IDC01424
BioCyc IDCPD-183
BiGG IDNot Available
Wikipedia LinkGallic_acid
METLIN ID3295
PubChem Compound370
PDB IDNot Available
ChEBI ID30778
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000474
Good Scents IDrw1099031
References
Synthesis ReferenceCheng K F; Yip C S; Yeung H W; Kong Y C Leonurine, an improved synthesis. Experientia (1979), 35(5), 571-2. PubMed ID 446644
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Bajpai B, Patil S: A new approach to microbial production of gallic acid. Braz J Microbiol. 2008 Oct;39(4):708-11. doi: 10.1590/S1517-838220080004000021. Epub 2008 Dec 1. [PubMed:24031294 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Gallic acid → 6-(5-carboxy-2,3-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Gallic acid → 6-(4-carboxy-2,6-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Gallic acid → 3,4,5-trihydroxy-6-(3,4,5-trihydroxybenzoyloxy)oxane-2-carboxylic aciddetails
Enzyme Details
2. Glycine N-acyltransferase
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
Reactions
Gallic acid → 2-{[hydroxy(3,4,5-trihydroxyphenyl)methylidene]amino}acetic aciddetails
Enzyme Details
3. Sulfotransferase 1A3
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Gallic acid → 3,5-dihydroxy-4-(sulfooxy)benzoic aciddetails