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Showing NP-Card for 2,5-Dihydroxybenzoic acid (NP0331705)

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Record Information
Version2.0
Created at2023-06-29 00:00:54 UTC
Updated at2024-09-03 04:16:34 UTC
NP-MRD IDNP0331705
Natural Product DOIhttps://doi.org/10.57994/0713
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,5-Dihydroxybenzoic 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 exists in all living organisms, ranging from bacteria to humans. Gentisic 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. 2,5-Dihydroxybenzoic acid was first documented in 2021 (PMID: 33499159). Based on a literature review a significant number of articles have been published on Gentisic acid (PMID: 34402687) (PMID: 34500788) (PMID: 34500294) (PMID: 34337757) (PMID: 34276578) (PMID: 34250876).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0331705 (2,5-Dihydroxybenzoic 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 NP0331705 (2,5-Dihydroxybenzoic 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 NP0331705 (2,5-Dihydroxybenzoic 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>
NP0331705

> <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 NP0331705 (2,5-Dihydroxybenzoic 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 NP0331705 (2,5-Dihydroxybenzoic 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 NP0331705 (2,5-Dihydroxybenzoic 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 NP0331705 (2,5-Dihydroxybenzoic acid)

OC(=O)C1=C(O)C=CC(O)=C1
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INCHI for NP0331705 (2,5-Dihydroxybenzoic 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 NumberNot Available
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
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2024-05-09View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2024-05-09View 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
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-09View Spectrum
Species
Species of OriginNot Available
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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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. Tigu AB, Moldovan CS, Toma VA, Farcas AD, Mot AC, Jurj A, Fischer-Fodor E, Mircea C, Parvu M: Phytochemical Analysis and In Vitro Effects of Allium fistulosum L. and Allium sativum L. Extracts on Human Normal and Tumor Cell Lines: A Comparative Study. Molecules. 2021 Jan 22;26(3). pii: molecules26030574. doi: 10.3390/molecules26030574. [PubMed:33499159 ]
  2. Chakraborty A, Mitra A, Tawate M, Sahoo S, Lad S, Rakshit S, Gaikwad S, Basu S, Shimpi H, Banerjee S: Therapeutic Multidose Preparation of a Ready-to-Use (177)Lu-PSMA-617 Using Carrier Added Lutetium-177 in a Hospital Radiopharmacy and Its Clinical Efficacy. Cancer Biother Radiopharm. 2021 Aug 16. doi: 10.1089/cbr.2020.4261. [PubMed:34402687 ]
  3. Jin N, Jin L, Luo S, Tang Z, Liu Z, Wei S, Liu F, Zhao X, Yu J, Zhong Y: Comprehensive Evaluation of Amino Acids and Polyphenols in 69 Varieties of Green Cabbage (Brassica oleracea L. var. capitata L.) Based on Multivariate Statistical Analysis. Molecules. 2021 Sep 3;26(17):5355. doi: 10.3390/molecules26175355. [PubMed:34500788 ]
  4. Li H, Pan Y, Li C, Yang Z, Rao J, Chen B: Design, synthesis and characterization of lysozyme-gentisic acid dual-functional conjugates with antibacterial/antioxidant activities. Food Chem. 2022 Feb 15;370:131032. doi: 10.1016/j.foodchem.2021.131032. Epub 2021 Sep 2. [PubMed:34500294 ]
  5. Mostafa HS: Banana plant as a source of valuable antimicrobial compounds and its current applications in the food sector. J Food Sci. 2021 Sep;86(9):3778-3797. doi: 10.1111/1750-3841.15854. Epub 2021 Aug 1. [PubMed:34337757 ]
  6. Poirier W, Ravenel K, Bouchara JP, Giraud S: Lower Funneling Pathways in Scedosporium Species. Front Microbiol. 2021 Jul 2;12:630753. doi: 10.3389/fmicb.2021.630753. eCollection 2021. [PubMed:34276578 ]
  7. Dumond ARS, Rodnick ME, Piert MR, Scott PJH: Synthesis of (225)Ac-PSMA-617 for Preclinical Use. Curr Radiopharm. 2022;15(2):96-103. doi: 10.2174/1874471014666210709094616. [PubMed:34250876 ]
  8. Kang MJ, Choi W, Yoo SH, Nam SW, Shin PG, Kim KK, Kim GD: Modulation of Inflammatory Pathways and Adipogenesis by the Action of Gentisic Acid in RAW 264.7 and 3T3-L1 Cell Lines. J Microbiol Biotechnol. 2021 Aug 28;31(8):1079-1087. doi: 10.4014/jmb.2105.05004. [PubMed:34226400 ]
  9. Pujari RR, Bandawane DD: Hepatoprotective Activity of Gentisic Acid on 5-Fluorouracil-induced Hepatotoxicity in Wistar Rats. Turk J Pharm Sci. 2021 Jun 18;18(3):332-338. doi: 10.4274/tjps.galenos.2020.95870. [PubMed:34157823 ]
  10. Portieles R, Xu H, Yue Q, Zhao L, Zhang D, Du L, Gao X, Gao J, Portal Gonzalez N, Santos Bermudez R, Borras-Hidalgo O: Heat-killed endophytic bacterium induces robust plant defense responses against important pathogens. Sci Rep. 2021 Jun 9;11(1):12182. doi: 10.1038/s41598-021-91837-5. [PubMed:34108579 ]
  11. Baudhuin H, Cousaert J, Vanwolleghem P, Raes G, Caveliers V, Keyaerts M, Lahoutte T, Xavier C: (68)Ga-Labeling: Laying the Foundation for an Anti-Radiolytic Formulation for NOTA-sdAb PET Tracers. Pharmaceuticals (Basel). 2021 May 10;14(5):448. doi: 10.3390/ph14050448. [PubMed:34068666 ]
  12. Gupta P, De B: Influence of calcium channel modulators on the production of serotonin, gentisic acid, and a few other biosynthetically related phenolic metabolites in seedling leaves of salt tolerant rice variety Nonabokra. Plant Signal Behav. 2021 Oct 3;16(10):1929732. doi: 10.1080/15592324.2021.1929732. Epub 2021 May 23. [PubMed:34024248 ]
  13. Divyashri G, Krishna Murthy TP, Sundareshan S, Kamath P, Murahari M, Saraswathy GR, Sadanandan B: In silico approach towards the identification of potential inhibitors from Curcuma amada Roxb against H. pylori: ADMET screening and molecular docking studies. Bioimpacts. 2021;11(2):119-127. doi: 10.34172/bi.2021.19. Epub 2020 Mar 24. [PubMed:33842282 ]
  14. Manal Ahmad A, Yasser Ibrahim K, Manal Mohammad A: Efficacy of extract from Ononis spinosa L. on ethanol-induced gastric ulcer in rats. J Tradit Chin Med. 2021 Apr;41(2):270-275. [PubMed:33825407 ]
  15. Mechchate H, Es-Safi I, Mohamed Al Kamaly O, Bousta D: Insight into Gentisic Acid Antidiabetic Potential Using In Vitro and In Silico Approaches. Molecules. 2021 Mar 30;26(7):1932. doi: 10.3390/molecules26071932. [PubMed:33808152 ]
  16. Feuya Tchouya GR, Foundikou H, Mbiantcha M, Kezetas JJB, Bongui JB, Tchouankeu JC, Lebibi J, Dethe DH: A new dibenzofuran derivative from the stem bark of Scyphocephalium ochocoa with anti-inflammatory and cytotoxic activities. Nat Prod Res. 2022 Mar;36(6):1503-1514. doi: 10.1080/14786419.2021.1894561. Epub 2021 Mar 4. [PubMed:33663283 ]
  17. Nazareth MS, Shreelakshmi SV, Shetty NP: Identification and Characterization of Polyphenols from Carissa spinarum Fruit and Evaluation of Their Antioxidant and Anti-quorum Sensing Activity. Curr Microbiol. 2021 Apr;78(4):1277-1285. doi: 10.1007/s00284-021-02381-4. Epub 2021 Feb 26. [PubMed:33634411 ]
  18. Al Khatib M, Costa J, Spinelli D, Capecchi E, Saladino R, Baratto MC, Pogni R: Homogentisic Acid and Gentisic Acid Biosynthesized Pyomelanin Mimics: Structural Characterization and Antioxidant Activity. Int J Mol Sci. 2021 Feb 9;22(4):1739. doi: 10.3390/ijms22041739. [PubMed:33572316 ]
  19. Vega-Ruiz YC, Hayano-Kanashiro C, Gamez-Meza N, Medina-Juarez LA: Determination of Chemical Constituents and Antioxidant Activities of Leaves and Stems from Jatropha cinerea (Ortega) Mull. Arg and Jatropha cordata (Ortega) Mull. Arg. Plants (Basel). 2021 Jan 22;10(2):212. doi: 10.3390/plants10020212. [PubMed:33499190 ]