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Showing NP-Card for Gentisic acid (NP0000017)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-09-03 04:19:19 UTC
NP-MRD IDNP0000017
Natural Product DOIhttps://doi.org/10.57994/1714
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000017 (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
Download

3D MOL for NP0000017 (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
Download

3D SDF for NP0000017 (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>
NP0000017

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0000017 (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
Download

PDB for NP0000017 (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 NP0000017 (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 NP0000017 (Gentisic acid)

OC(=O)C1=C(O)C=CC(O)=C1
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INCHI for NP0000017 (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 JSmol
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
Hydroquinone carboxylic acidHMDB
Gentisic acidChEBI
Chemical FormulaC7H6O4
Average Mass154.1210 Da
Monoisotopic Mass154.02661 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium obliquumPlant
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum foeniculumPlant
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arachis hypogaeaFooDB
Arbutus unedoLOTUS Database
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Betula pendulaLOTUS Database
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Castanopsis fissaLOTUS Database
Catharanthus roseusPlant
Centella asiaticaLOTUS Database
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chelidonium majusLOTUS Database
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus cultivarsKNApSAcK Database
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus limoniaKNApSAcK Database
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus spp.KNApSAcK Database
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Cotoneaster orbicularisLOTUS Database
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cymodocea rotundataKNApSAcK Database
Cymodocea serrulataKNApSAcK Database
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros lotusLOTUS Database
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Ervatamia coronariaLOTUS Database
Eucalyptus grandisKNApSAcK Database
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Euthamia graminifoliaLOTUS Database
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareKNApSAcK Database
Fragaria x ananassaFooDB
Fumaria capreolataPlant
Fumaria officinalisPlant
Fumaria schleicheriPlant
Fumaria vaillantiiPlant
Gallus gallusFooDB
Ganoderma applanatumLOTUS Database
Garcinia mangostanaFooDB
Gaultheria procumbensLOTUS Database
Gaylussacia baccataFooDB
Gentiana spp.KNApSAcK Database
Ginkgo bilobaFooDB
Gliricidia sepiumLOTUS Database
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Halodule uninervisKNApSAcK Database
Halodule wrightiiKNApSAcK Database
Halophila hawaiianaKNApSAcK Database
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusKNApSAcK Database
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Leptolaena diospyroideaKNApSAcK Database
Leptolaena paucifloraKNApSAcK Database
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
Lycopus europaeusLOTUS Database
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Menyanthes trifoliataLOTUS Database
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaPlant
Moringa peregrinaPlant
Moringa stenopetalaPlant
MorusFooDB
Morus nigraFooDB
Mus musculusLOTUS Database
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaKNApSAcK Database
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Penicillium citrinumLOTUS Database
Penicillium griseofulvumLOTUS Database
Penicillium solitumLOTUS Database
Perideridia oreganaFooDB
Persea americanaFooDB
Persicaria lapathifoliaLOTUS Database
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllospadix scouleriKNApSAcK Database
Phyllospadix serrulatusKNApSAcK Database
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Pinus montanaLOTUS Database
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Plantago majorKNApSAcK Database
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Polyporus tumulosusLOTUS Database
Portulaca oleraceaFooDB
Posidonia oceanicaKNApSAcK Database
Pouteria sapotaFooDB
Primula acaulisLOTUS Database
Prunus armeniacaFooDB
Prunus aviumKNApSAcK Database
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Pterocarpus santalinusKNApSAcK Database
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusKNApSAcK Database
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rhamnus dispermaKNApSAcK Database
Rhaponticum carthamoidesKNApSAcK Database
Rheum rhabarbarumFooDB
Rhododendron dauricumLOTUS Database
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Sarcolaeana multiflora-
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Scrophularia frutescensPlant
Secale cerealeFooDB
Secamone afzeliiLOTUS Database
Sechium eduleFooDB
Sesamum indicumKNApSAcK Database
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Streptomyces cinnamonensisLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syringodium filiformeKNApSAcK Database
Syringodium isoetifoliumKNApSAcK Database
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Taxus baccataKNApSAcK Database
Tetragonia tetragonioidesFooDB
Thalassia hemprichiiKNApSAcK Database
Thalassia testudinumKNApSAcK Database
Thalassodendron ciliatumKNApSAcK Database
ThelespermaFooDB
Theobroma cacaoFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tilia tomentosaLOTUS Database
Tragopogon porrifoliusFooDB
Tragopogon pratensisLOTUS Database
Tremella fuciformisLOTUS Database
Trifolium pratensePlant
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Triticum turgidumLOTUS Database
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Veronica officinalisPlant
Veronica orchideaPlant
Veronica teucriumPlant
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis viniferaKNApSAcK Database
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Zostera capricorniKNApSAcK Database
Zostera marinaKNApSAcK Database
Species Where Detected
Species NameSourceReference
Penicillium citrinum F5KNApSAcK Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point199.5 °CNot Available
Boiling Point406.00 to 407.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility5 mg/mL at 5 °CNot Available
LogP1.74Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted 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
HMDB IDHMDB0000152
DrugBank IDNot Available
Phenol Explorer Compound ID416
FoodDB 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
Good Scents IDrw1165361
References
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. 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 ]
  3. 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 ]
  4. Peleg H, Noble AC: Perceptual properties of benzoic acid derivatives. Chem Senses. 1995 Aug;20(4):393-400. [PubMed:8590024 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]