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Showing NP-Card for 2,6-Dihydroxybenzoic acid (NP0045442)

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Record Information
Version2.0
Created at2022-03-17 19:20:02 UTC
Updated at2025-02-11 15:47:45 UTC
NP-MRD IDNP0045442
Natural Product DOIhttps://doi.org/10.57994/2713
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,6-Dihydroxybenzoic acid
Description2,6-Dihydroxybenzoic acid, also known as 6-hydroxysalicylic acid or gamma-resorcylic acid, belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids. 2,6-Dihydroxybenzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2,6-Dihydroxybenzoic acid is found, on average, in the highest concentration within beers and olives. This could make 2,6-dihydroxybenzoic acid a potential biomarker for the consumption of these foods. 2,6-Dihydroxybenzoic acid is found in Alangium platanifolium, Graphis proserpens, Oenothera grandiflora, Persea americana, Pinus mugo, Polygonum cuspidatum and Rumex japonicus. 2,6-Dihydroxybenzoic acid is a secondary metabolite of salicylic acid which has been hydrolyzed by liver enzymes during phase I metabolism.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045442 (2,6-Dihydroxybenzoic acid)

2,6-Dihydroxybenzoic acid
  Mrv1652303102016532D          

 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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   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  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for NP0045442 (2,6-Dihydroxybenzoic acid)

     RDKit          3D

 17 17  0  0  0  0  0  0  0  0999 V2000
    2.5375   -0.9861   -1.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8548   -0.0711   -0.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5351    1.1513   -0.5268 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4801   -0.1588   -0.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2755   -1.2997   -0.3508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2190   -2.4676   -0.8535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6133   -1.2880    0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1484   -0.1468    0.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4259    1.0129    0.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1226    0.9981    0.2782 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6347    2.1518    0.3762 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1840    1.2148    0.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1259   -2.6174   -1.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -2.2121   -0.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1787   -0.1701    0.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8506    1.9010    1.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2168    2.9878    0.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10  4  1  0
  3 12  1  0
  6 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 NP0045442 (2,6-Dihydroxybenzoic acid)

2,6-Dihydroxybenzoic acid
  Mrv1652303102016532D          

 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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   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  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045442

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=C(O)C=CC=C1O

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

> <INCHI_KEY>
AKEUNCKRJATALU-UHFFFAOYSA-N

> <FORMULA>
C7H6O4

> <MOLECULAR_WEIGHT>
154.121

> <EXACT_MASS>
154.026608673

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.673414430971047

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,6-dihydroxybenzoic acid

> <ALOGPS_LOGP>
1.28

> <JCHEM_LOGP>
2.3236980806666665

> <ALOGPS_LOGS>
-1.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.256501187441199

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5141995841754006

> <JCHEM_PKA_STRONGEST_BASIC>
-5.989155147862662

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
37.275999999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.49e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6-dihydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0045442 (2,6-Dihydroxybenzoic acid)

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PDB for NP0045442 (2,6-Dihydroxybenzoic acid)
HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2,6-Dihydroxybenzoic acid                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-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  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0045442 (2,6-Dihydroxybenzoic acid)
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SMILES for NP0045442 (2,6-Dihydroxybenzoic acid)
OC(=O)C1=C(O)C=CC=C1O
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INCHI for NP0045442 (2,6-Dihydroxybenzoic acid)
InChI=1S/C7H6O4/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3,8-9H,(H,10,11)
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Synonyms
ValueSource
6-Hydroxysalicylic acidChEBI
gamma-Resorcylic acidChEBI
6-HydroxysalicylateGenerator
g-ResorcylateGenerator
g-Resorcylic acidGenerator
gamma-ResorcylateGenerator
Γ-resorcylateGenerator
Γ-resorcylic acidGenerator
2,6-DihydroxybenzoateGenerator
2,6-Dihydroxy-benzoic acidHMDB
2,6-Dihydroxybenzoic acid (acd/name 4.0)HMDB
2,6-Resorcylic acidHMDB
2-CarboxyresorcinolHMDB
BenzoateHMDB
Benzoic acidHMDB
Chemical FormulaC7H6O4
Average Mass154.1210 Da
Monoisotopic Mass154.02661 Da
IUPAC Name2,6-dihydroxybenzoic acid
Traditional Name2,6-dihydroxybenzoic acid
CAS Registry Number303-07-1
SMILES
OC(=O)C1=C(O)C=CC=C1O
InChI Identifier
InChI=1S/C7H6O4/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3,8-9H,(H,10,11)
InChI KeyAKEUNCKRJATALU-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)[email protected]Sumner lab, University of MissouriZach Tretter2024-06-03View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)[email protected]Sumner lab, University of MissouriZach Tretter2024-06-03View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)[email protected]Sumner lab, University of MissouriZach Tretter2024-06-03View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)[email protected]Sumner lab, University of MissouriZach Tretter2024-06-03View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CD3OD, experimental)[email protected]Sumner lab, University of MissouriZach Tretter2024-06-03View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)[email protected]Sumner lab, University of MissouriZach Tretter2024-06-03View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 800, CD3OD, simulated)[email protected]Sumner lab, University of MissouriZach Tretter2024-06-03View Spectrum
Species
Species of Origin
Species NameSourceReference
Alangium platanifoliumLOTUS Database
Fragaria x ananassaFooDB
Graphis proserpensLOTUS Database
Oenothera grandifloraLOTUS Database
Olea europaeaFooDB
Persea americanaLOTUS Database
Pinus montanaLOTUS Database
Polygonum cuspidatumPlant
Rumex japonicusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzoic acids and derivatives  
Direct ParentSalicylic acids  
Alternative Parents
Substituents
  • Salicylic acid
    • 

  • Benzoic acid
    • 

  • Benzoyl
    • 

  • Resorcinol
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Vinylogous acid
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP1.28ALOGPS
logP2.32ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.28 m³·mol⁻¹ChemAxon
Polarizability13.67 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013676  
DrugBank IDNot Available
Phenol Explorer Compound ID437  
FoodDB IDFDB000845  
KNApSAcK IDNot Available
Chemspider ID8974  
KEGG Compound IDNot Available
BioCyc IDCPD-8816  
BiGG IDNot Available
Wikipedia Link2,6-Dihydroxybenzoic_acid  
METLIN IDNot Available
PubChem Compound9338  
PDB IDGRE  
ChEBI ID68465  
Good Scents IDNot Available
References
General References