Showing metabocard for Gallic acid (MMDBc0029691)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:37:44 UTC
Update Date2024-04-30 19:40:45 UTC
Metabolite IDMMDBc0029691
Metabolite Identification
Common NameGallic acid
DescriptionGallic acid (GA) is an organic acid, also known as 3,4,5-trihydroxybenzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. Plants, bacteria and fungi are capable of synthesizing gallic acid. Shikimate dehydrogenase (SDH), a shikimate pathway enzyme essential for aromatic amino acid synthesis, is required for gallic acid production in Escherichia coli. SDH catalyzes NADPH-dependent reduction of 3-DHS (3-dehydroshikimate) to shikimic acid (SA), which is ultimately used to produce the aromatic amino acids l-tyrosine, l-tryptophan, and l-phenylalanine. SDH also catalyzes NADP+-dependent dehydrogenation of SA to 3-DHS, but also the dehydrogenation of 3-DHS to GA.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fe2641b2760>


  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 #<Metabolite:0x00007fe2641b2760>

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 #<Metabolite:0x00007fe2641b2760>


  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>
MMDBc0029691

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007fe2641b2760>

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

PDB for #<Metabolite:0x00007fe2641b2760>

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 #<Metabolite:0x00007fe2641b2760>

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 #<Metabolite:0x00007fe2641b2760>

OC(=O)C1=CC(O)=C(O)C(O)=C1
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INCHI for #<Metabolite:0x00007fe2641b2760>

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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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
Molecular FormulaC7H6O5
Average Mass170.12
Monoisotopic Mass170.021523293
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