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Showing metabocard for Gentisic acid (HMDB0000152)

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enzymes (3) Show 3 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:34 UTC
HMDB IDHMDB0000152
Secondary Accession Numbers
  • HMDB00152
Metabolite Identification
Common NameGentisic acid
DescriptionGentisic acid, also known as gentisate or 2,5-dioxybenzoate, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. Gentisic acid is also classified as a dihydroxybenzoic acid. It is a derivative of benzoic acid and a minor (1%) product of the metabolic break down of aspirin, which is excreted by the kidneys. Gentisic acid is found in essentially all organisms ranging from bacteria to fungi to plants to animals. Gentisic acid has been associated with a number of useful effects on human health and exhibits anti-inflammatory, antigenotoxic, hepatoprotective, neuroprotective, antimicrobial, and especially antioxidant activities (PMID: 31825145 ). It is widely distributed in plants as a secondary plant product such as Gentiana spp., Citrus spp., Vitis vinifera, Pterocarpus santalinus, Helianthus tuberosus, Hibiscus rosa-sinensis, Olea europaea, and Sesamum indicum and in fruits such as avocados, batoko plum, kiwi fruits, apple, bitter melon, black berries, pears, and some mushrooms (PMID: 31825145 ). Gentisic acid is found in higher concentrations in a number of foods such as tarragons, common thymes, and common sages and in a lower concentration in grape wines, rosemaries, and sweet marjorams. Gentisic acid has also been shown to act as a pathogen-inducible signal for the activation of plant defenses in tomato plants and cucumbers (PMID: 16321412 ; https://doi.org/10.1094/MPMI.1999.12.3.227).
Structure
Data?1676999674
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000152 (Gentisic acid)

Gentisic acid
  Mrv1652309032023542D          

 11 11  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  4 11  1  0  0  0  0
M  END
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3D MOL for HMDB0000152 (Gentisic acid)

HMDB0000152
     RDKit          3D
Gentisic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.6682    1.3941   -0.1686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4366    1.6222   -0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9122    2.8905   -0.2711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5028    0.5047   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8639    0.6917   -0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080   -0.3877    0.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0957   -0.1994    0.0117 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2557   -1.6913    0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1114   -1.8648    0.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9783   -0.7973    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3573   -0.9558    0.0210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3779    3.6400    0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2290    1.7171   -0.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4879    0.7448   -0.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9215   -2.5408    0.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5043   -2.8689    0.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7126   -1.8992    0.0926 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
  9 10  2  0
 10 11  1  0
 10  4  1  0
  3 12  1  0
  5 13  1  0
  7 14  1  0
  8 15  1  0
  9 16  1  0
 11 17  1  0
M  END
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3D SDF for HMDB0000152 (Gentisic acid)

Gentisic acid
  Mrv1652309032023542D          

 11 11  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  4 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000152

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)

> <INCHI_KEY>
WXTMDXOMEHJXQO-UHFFFAOYSA-N

> <FORMULA>
C7H6O4

> <MOLECULAR_WEIGHT>
154.121

> <EXACT_MASS>
154.026608673

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.777778121056386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,5-dihydroxybenzoic acid

> <ALOGPS_LOGP>
1.23

> <JCHEM_LOGP>
1.6736980806666664

> <ALOGPS_LOGS>
-1.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.024335409652737

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5281776702814094

> <JCHEM_PKA_STRONGEST_BASIC>
-5.934430569892133

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
37.276

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dihydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000152 (Gentisic acid)

HMDB0000152
     RDKit          3D
Gentisic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.6682    1.3941   -0.1686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4366    1.6222   -0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9122    2.8905   -0.2711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5028    0.5047   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8639    0.6917   -0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080   -0.3877    0.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0957   -0.1994    0.0117 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2557   -1.6913    0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1114   -1.8648    0.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9783   -0.7973    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3573   -0.9558    0.0210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3779    3.6400    0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2290    1.7171   -0.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4879    0.7448   -0.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9215   -2.5408    0.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5043   -2.8689    0.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7126   -1.8992    0.0926 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
  9 10  2  0
 10 11  1  0
 10  4  1  0
  3 12  1  0
  5 13  1  0
  7 14  1  0
  8 15  1  0
  9 16  1  0
 11 17  1  0
M  END
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PDB for HMDB0000152 (Gentisic acid)

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Gentisic acid                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0000152 (Gentisic acid)

COMPND    HMDB0000152
HETATM    1  O1  UNL     1      -2.668   1.394  -0.169  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.437   1.622  -0.175  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.912   2.890  -0.271  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.503   0.505  -0.078  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.864   0.692  -0.080  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.708  -0.388   0.014  1.00  0.00           C  
HETATM    7  O3  UNL     1       3.096  -0.199   0.012  1.00  0.00           O  
HETATM    8  C5  UNL     1       1.256  -1.691   0.113  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.111  -1.865   0.114  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.978  -0.797   0.021  1.00  0.00           C  
HETATM   11  O4  UNL     1      -2.357  -0.956   0.021  1.00  0.00           O  
HETATM   12  H1  UNL     1      -1.378   3.640   0.226  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.229   1.717  -0.158  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.488   0.745  -0.060  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.921  -2.541   0.187  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.504  -2.869   0.190  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.713  -1.899   0.093  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5    5   10
CONECT    5    6   13
CONECT    6    7    8    8
CONECT    7   14
CONECT    8    9   15
CONECT    9   10   10   16
CONECT   10   11
CONECT   11   17
END
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SMILES for HMDB0000152 (Gentisic acid)

OC(=O)C1=C(O)C=CC(O)=C1
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INCHI for HMDB0000152 (Gentisic acid)

InChI=1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2,5-DihydroxybenzoateChEBI
5-Hydroxysalicylic acidChEBI
GentisateChEBI
Hydroquinonecarboxylic acidChEBI
2,5-Dihydroxybenzoic acidKegg
5-HydroxysalicylateGenerator
HydroquinonecarboxylateGenerator
2,5-DioxybenzoateHMDB
2,5-Dioxybenzoic acidHMDB
3,6-DihydroxybenzoateHMDB
3,6-Dihydroxybenzoic acidHMDB
5-Hydroxy-salicylateHMDB
5-Hydroxy-salicylic acidHMDB
CarboxyhydroquinoneHMDB
DihydroxybenzoicacidHMDB
GensigenHMDB
GensigonHMDB
GentisinateHMDB
Gentisinic acidHMDB
2,5-Dihydroxybenzoic acid, monosodium saltHMDB
Lithium 2,5-dihydroxybenzoateHMDB
Gentisic acidChEBI
Hydroquinone carboxylic acidHMDB
Chemical FormulaC7H6O4
Average Molecular Weight154.121
Monoisotopic Molecular Weight154.026608673
IUPAC Name2,5-dihydroxybenzoic acid
Traditional Name2,5-dihydroxybenzoic acid
CAS Registry Number490-79-9
SMILES
OC(=O)C1=C(O)C=CC(O)=C1
InChI Identifier
InChI=1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)
InChI KeyWXTMDXOMEHJXQO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Dihydroxybenzoic acid
  • Salicylic acid
  • Salicylic acid or derivatives
  • Hydroxybenzoic acid
  • Benzoic acid
  • Benzoyl
  • Hydroquinone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point199.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5 mg/mL at 5 °CNot Available
LogP1.74SANGSTER (1994)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg122.67230932474
[M-H]-Not Available124.5http://allccs.zhulab.cn/database/detail?ID=AllCCS00000286
Predicted Molecular Properties
PropertyValueSource
Water Solubility12.3 g/LALOGPS
logP1.23ALOGPS
logP1.67ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)2.53ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.28 m³·mol⁻¹ChemAxon
Polarizability13.78 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]+132.48431661259
DarkChem[M-H]-129.18131661259
AllCCS[M+H]+132.58632859911
AllCCS[M-H]-125.70832859911
DeepCCS[M+H]+133.10830932474
DeepCCS[M-H]-129.43230932474
DeepCCS[M-2H]-167.14330932474
DeepCCS[M+Na]+142.68230932474
AllCCS[M+H]+132.632859911
AllCCS[M+H-H2O]+128.032859911
AllCCS[M+NH4]+136.832859911
AllCCS[M+Na]+138.032859911
AllCCS[M-H]-125.732859911
AllCCS[M+Na-2H]-127.032859911
AllCCS[M+HCOO]-128.432859911

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, 2022.2.39 minutes32390414
Predicted by Siyang on May 30, 20229.8664 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.1 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid80.9 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1080.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid324.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid80.3 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid195.0 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid95.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid367.9 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 Acid356.2 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)152.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid655.8 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid255.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1012.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid228.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid288.6 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate639.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA231.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water261.2 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Gentisic acidOC(=O)C1=C(O)C=CC(O)=C12929.7Standard polar33892256
Gentisic acidOC(=O)C1=C(O)C=CC(O)=C11547.3Standard non polar33892256
Gentisic acidOC(=O)C1=C(O)C=CC(O)=C11504.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Gentisic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(O)=CC=C1O1724.4Semi standard non polar33892256
Gentisic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(O)C=C1C(=O)O1744.4Semi standard non polar33892256
Gentisic acid,1TMS,isomer #3C[Si](C)(C)OC1=CC=C(O)C(C(=O)O)=C11736.1Semi standard non polar33892256
Gentisic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=CC=C1O1711.3Semi standard non polar33892256
Gentisic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC(O)=CC=C1O[Si](C)(C)C1765.1Semi standard non polar33892256
Gentisic acid,2TMS,isomer #3C[Si](C)(C)OC1=CC=C(O[Si](C)(C)C)C(C(=O)O)=C11783.2Semi standard non polar33892256
Gentisic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=CC=C1O[Si](C)(C)C1811.8Semi standard non polar33892256
Gentisic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=CC=C1O1986.2Semi standard non polar33892256
Gentisic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(O)C=C1C(=O)O1995.7Semi standard non polar33892256
Gentisic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(O)C(C(=O)O)=C11995.8Semi standard non polar33892256
Gentisic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1O2180.3Semi standard non polar33892256
Gentisic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=CC=C1O[Si](C)(C)C(C)(C)C2248.9Semi standard non polar33892256
Gentisic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=C12272.3Semi standard non polar33892256
Gentisic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2451.4Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.65 +/- 0.19 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified1.0 +/- 0.31 uMAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified1.35 +/- 0.79 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.31 +/- 0.19 uMAdult (>18 years old)BothIdiopathic oro-facial pain details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected and Quantified1.48 +/- 0.69 umol/mmol creatinineAdult (>18 years old)BothIdiopathic oro-facial pain details
Associated Disorders and Diseases
Disease References
Idiopathic oro-facial pain
  1. Aghabeigi B, Haque M, Wasil M, Hodges SJ, Henderson B, Harris M: The role of oxygen free radicals in idiopathic facial pain. Br J Oral Maxillofac Surg. 1997 Jun;35(3):161-5. [PubMed:9212290 ]
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 ID416
FooDB IDFDB000844
KNApSAcK IDC00002648
Chemspider ID3350
KEGG Compound IDC00628
BioCyc IDCPD-633
BiGG IDNot Available
Wikipedia LinkGentisic_acid
METLIN ID618
PubChem Compound3469
PDB IDNot Available
ChEBI ID17189
Food Biomarker OntologyNot Available
VMH IDHC00460
MarkerDB IDMDB00000073
Good Scents IDNot Available
References
Synthesis Reference Morris, Steward G. Preparation of gentisic acid and its fatty alcohol esters.Journal of the American Chemical Society (1949), 71 2056-7
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Ohsako M, Matsumoto Y, Goto S: Transport of aspirin and its metabolites through human erythrocyte membrane. Biol Pharm Bull. 1993 Feb;16(2):154-7. [PubMed:8364451 ]
  2. Almaas R, Rootwelt T, Oyasaeter S, Saugstad OD: Ascorbic acid enhances hydroxyl radical formation in iron-fortified infant cereals and infant formulas. Eur J Pediatr. 1997 Jun;156(6):488-92. [PubMed:9208249 ]
  3. Verhaeghe BJ, Lefevere MF, De Leenheer AP: Solid-phase extraction with strong anion-exchange columns for selective isolation and concentration of urinary organic acids. Clin Chem. 1988 Jun;34(6):1077-83. [PubMed:3378323 ]
  4. Palumbo G, Carlucci G, Mazzeo P, Frieri G, Pimpo MT, Fanini D: Simultaneous determination of 5-aminosalicylic acid, acetyl-5-aminosalicylic acid and 2,5-dihydroxybenzoic acid in endoscopic intestinal biopsy samples in humans by high-performance liquid chromatography with electrochemical detection. J Pharm Biomed Anal. 1995 Dec;14(1-2):175-80. [PubMed:8833980 ]
  5. Grootveld M, Halliwell B: Aromatic hydroxylation as a potential measure of hydroxyl-radical formation in vivo. Identification of hydroxylated derivatives of salicylate in human body fluids. Biochem J. 1986 Jul 15;237(2):499-504. [PubMed:3026319 ]
  6. Peleg H, Noble AC: Perceptual properties of benzoic acid derivatives. Chem Senses. 1995 Aug;20(4):393-400. [PubMed:8590024 ]
  7. Buskin JN, Upton RA, Williams RL: Improved liquid-chromatography of aspirin, salicylate, and salicyluric acid in plasma, with a modification for determining aspirin metabolites in urine. Clin Chem. 1982 May;28(5):1200-3. [PubMed:7074905 ]
  8. Liu JH, Smith PC: Direct analysis of salicylic acid, salicyl acyl glucuronide, salicyluric acid and gentisic acid in human plasma and urine by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Jan 12;675(1):61-70. [PubMed:8634769 ]
  9. Coudray C, Talla M, Martin S, Fatome M, Favier A: High-performance liquid chromatography-electrochemical determination of salicylate hydroxylation products as an in vivo marker of oxidative stress. Anal Biochem. 1995 May 1;227(1):101-11. [PubMed:7668368 ]
  10. Bochner F, Graham GG, Cham BE, Imhoff DM, Haavisto TM: Salicylate metabolite kinetics after several salicylates. Clin Pharmacol Ther. 1981 Aug;30(2):266-75. [PubMed:7249509 ]
  11. Cham BE, Bochner F, Imhoff DM, Johns D, Rowland M: Simultaneous liquid-chromatographic quantitation of salicylic acid, salicyluric acid, and gentisic acid in urine. Clin Chem. 1980 Jan;26(1):111-4. [PubMed:7356541 ]
  12. Abedi F, Razavi BM, Hosseinzadeh H: A review on gentisic acid as a plant derived phenolic acid and metabolite of aspirin: Comprehensive pharmacology, toxicology, and some pharmaceutical aspects. Phytother Res. 2020 Apr;34(4):729-741. doi: 10.1002/ptr.6573. Epub 2019 Dec 11. [PubMed:31825145 ]
  13. Fayos J, Belles JM, Lopez-Gresa MP, Primo J, Conejero V: Induction of gentisic acid 5-O-beta-D-xylopyranoside in tomato and cucumber plants infected by different pathogens. Phytochemistry. 2006 Jan;67(2):142-8. doi: 10.1016/j.phytochem.2005.10.014. [PubMed:16321412 ]

Enzymes

Enzyme Details
1. Aldehyde oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
Reactions
Gentisic acid + Hydrogen peroxide → Gentisate aldehyde + Oxygen + Waterdetails
Enzyme Details
2. 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
Gentisic acid → 6-(3-carboxy-4-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Gentisic acid → 6-(2-carboxy-4-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Gentisic acid → 6-(2,5-dihydroxybenzoyloxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Enzyme Details
3. 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
Gentisic acid → Gentisuric aciddetails