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Showing NP-Card for 4-hydroxybenzonicacid (NP0331797)

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Record Information
Version2.0
Created at2023-09-08 08:13:25 UTC
Updated at2024-09-03 04:16:59 UTC
NP-MRD IDNP0331797
Natural Product DOIhttps://doi.org/10.57994/0880
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-hydroxybenzonicacid
Description4-Hydroxybenzoic acid, also known as p-hydroxybenzoate or 4-carboxyphenol, 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. 4-Hydroxybenzoic acid exists in all living species, ranging from bacteria to plants to humans. In humans, 4-hydroxybenzoic acid is involved in the ubiquinone biosynthesis pathway. 4-Hydroxybenzoic 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. 4-hydroxybenzonicacid was first documented in 2021 (PMID: 34369151). Based on a literature review a significant number of articles have been published on 4-Hydroxybenzoic acid (PMID: 34322910) (PMID: 34325311) (PMID: 34583463) (PMID: 34562446) (PMID: 34543102) (PMID: 34519069).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0331797 (4-hydroxybenzonicacid)


  Mrv1652309272007372D          

 10 10  0  0  0  0            999 V2000
 9971.8991 9970.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9972.6113 9969.6370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9971.8991 9970.8717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9971.1883 9969.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.4738 9970.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9969.7592 9969.6378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9969.7592 9968.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.4736 9968.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9971.1883 9968.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9969.0469 9968.4016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9  4  1  0  0  0  0
  4  1  1  0  0  0  0
  1  2  1  0  0  0  0
  7 10  1  0  0  0  0
M  END
Download

3D MOL for NP0331797 (4-hydroxybenzonicacid)

HMDB0000500
     RDKit          3D
4-Hydroxybenzoic acid
 16 16  0  0  0  0  0  0  0  0999 V2000
   -3.0955    0.8809   -0.3676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3671   -0.0633    0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907   -1.2197    0.4934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9181    0.0673    0.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2998    1.2153   -0.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0966    1.3157   -0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8840    0.2760    0.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2760    0.3774    0.0940 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2317   -0.8584    0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1460   -0.9789    0.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4085   -1.8092   -0.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8927    2.0427   -0.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6007    2.2118   -0.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8603    0.0996   -0.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8200   -1.6869    0.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6508   -1.8704    0.8529 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  8 14  1  0
  9 15  1  0
 10 16  1  0
M  END
Download

3D SDF for NP0331797 (4-hydroxybenzonicacid)


  Mrv1652309272007372D          

 10 10  0  0  0  0            999 V2000
 9971.8991 9970.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9972.6113 9969.6370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9971.8991 9970.8717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9971.1883 9969.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.4738 9970.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9969.7592 9969.6378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9969.7592 9968.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.4736 9968.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9971.1883 9968.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9969.0469 9968.4016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9  4  1  0  0  0  0
  4  1  1  0  0  0  0
  1  2  1  0  0  0  0
  7 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331797

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)

> <INCHI_KEY>
FJKROLUGYXJWQN-UHFFFAOYSA-N

> <FORMULA>
C7H6O3

> <MOLECULAR_WEIGHT>
138.122

> <EXACT_MASS>
138.031694053

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.939727468110942

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxybenzoic acid

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
1.3272634023333332

> <ALOGPS_LOGS>
-1.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.67428543984855

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.379964053135935

> <JCHEM_PKA_STRONGEST_BASIC>
-6.063011046171021

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
35.2951

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
P-hydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0331797 (4-hydroxybenzonicacid)

HMDB0000500
     RDKit          3D
4-Hydroxybenzoic acid
 16 16  0  0  0  0  0  0  0  0999 V2000
   -3.0955    0.8809   -0.3676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3671   -0.0633    0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907   -1.2197    0.4934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9181    0.0673    0.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2998    1.2153   -0.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0966    1.3157   -0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8840    0.2760    0.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2760    0.3774    0.0940 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2317   -0.8584    0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1460   -0.9789    0.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4085   -1.8092   -0.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8927    2.0427   -0.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6007    2.2118   -0.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8603    0.0996   -0.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8200   -1.6869    0.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6508   -1.8704    0.8529 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  8 14  1  0
  9 15  1  0
 10 16  1  0
M  END
Download

PDB for NP0331797 (4-hydroxybenzonicacid)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8614.2128610.757   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8615.5418609.989   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8614.2128612.294   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8612.8858609.991   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8611.5518610.761   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8610.2178609.991   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8610.2178608.451   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8611.5518607.681   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8612.8858608.451   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8608.8888607.683   0.000  0.00  0.00           O+0
CONECT    1    3    4    2                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    5    9    1                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
Download

3D PDB for NP0331797 (4-hydroxybenzonicacid)

COMPND    HMDB0000500
HETATM    1  O1  UNL     1      -3.095   0.881  -0.368  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.367  -0.063   0.047  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.991  -1.220   0.493  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.918   0.067   0.052  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.300   1.215  -0.392  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.097   1.316  -0.376  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.884   0.276   0.079  1.00  0.00           C  
HETATM    8  O3  UNL     1       3.276   0.377   0.094  1.00  0.00           O  
HETATM    9  C6  UNL     1       1.232  -0.858   0.516  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.146  -0.979   0.510  1.00  0.00           C  
HETATM   11  H1  UNL     1      -3.409  -1.809  -0.231  1.00  0.00           H  
HETATM   12  H2  UNL     1      -0.893   2.043  -0.753  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.601   2.212  -0.722  1.00  0.00           H  
HETATM   14  H4  UNL     1       3.860   0.100  -0.680  1.00  0.00           H  
HETATM   15  H5  UNL     1       1.820  -1.687   0.877  1.00  0.00           H  
HETATM   16  H6  UNL     1      -0.651  -1.870   0.853  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   11
CONECT    4    5    5   10
CONECT    5    6   12
CONECT    6    7    7   13
CONECT    7    8    9
CONECT    8   14
CONECT    9   10   10   15
CONECT   10   16
END
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SMILES for NP0331797 (4-hydroxybenzonicacid)

OC(=O)C1=CC=C(O)C=C1
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INCHI for NP0331797 (4-hydroxybenzonicacid)

InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)
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View in JSmol
Synonyms
ValueSource
4-CarboxyphenolChEBI
p-HYDROXYBENZOIC ACIDChEBI
p-Salicylic acidChEBI
Hydroxybenzoic acidKegg
Hydroxybenzenecarboxylic acidKegg
p-HYDROXYBENZOateGenerator
p-SalicylateGenerator
HydroxybenzoateGenerator
HydroxybenzenecarboxylateGenerator
4-HydroxybenzoateGenerator
4-Hydroxy-benzoateHMDB
4-Hydroxy-benzoesaeureHMDB
4-Hydroxy-benzoic acidHMDB
p-CarboxyphenolHMDB
p-Hydroxy-benzoateHMDB
p-Hydroxy-benzoic acidHMDB
Paraben-acidHMDB
4-Hydroxybenzoic acid, calcium saltHMDB
4-Hydroxybenzoic acid, dilithium saltHMDB
4-Hydroxybenzoic acid, disodium saltHMDB
Para-hydroxybenzoic acidHMDB
Sodium p-hydroxybenzoate tetrahydrateHMDB
4-Hydroxybenzoic acid, copper(2+)(1:1) saltHMDB
4-Hydroxybenzoic acid, dipotassium saltHMDB
4-Hydroxybenzoic acid, monopotassium saltHMDB
4-Hydroxybenzoic acid, monosodium saltHMDB
4-Hydroxybenzoic acid, monosodium salt, 11C-labeledHMDB
4-Hydroxybenzene carboxylic acidHMDB
p-Hydroxyl benzoic acidHMDB
Chemical FormulaC7H6O3
Average Mass138.1220 Da
Monoisotopic Mass138.03169 Da
IUPAC Name4-hydroxybenzoic acid
Traditional NameP-hydroxybenzoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)
InChI KeyFJKROLUGYXJWQN-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)wuhonghua2011@tjutcm.edu.cnTianjin University of Traditional Chinese MedicineHong-Hua Wu2023-09-08View Spectrum
1D NMR1H NMR Spectrum (1D, 500 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 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
  • Hydroxybenzoic acid
  • Benzoic acid
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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
logP1.58ALOGPS
logP1.33ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)4.38ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.3 m³·mol⁻¹ChemAxon
Polarizability12.94 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000500
DrugBank IDDB04242
Phenol Explorer Compound ID418
FoodDB IDFDB010508
KNApSAcK IDC00000856
Chemspider ID132
KEGG Compound IDC00156
BioCyc ID4-hydroxybenzoate
BiGG ID34069
Wikipedia Link4-Hydroxybenzoic_acid
METLIN ID5486
PubChem Compound135
PDB IDNot Available
ChEBI ID30763
Good Scents IDrw1040201
References
General References
  1. Flachbart LK, Gertzen CGW, Gohlke H, Marienhagen J: Development of a Biosensor Platform for Phenolic Compounds Using a Transition Ligand Strategy. ACS Synth Biol. 2021 Aug 9. doi: 10.1021/acssynbio.1c00165. [PubMed:34369151 ]
  2. Di Lella S, La Porta N, Tognetti R, Lombardi F, Nardin T, Larcher R: White rot fungal impact on the evolution of simple phenols during decay of silver fir wood by UHPLC-HQOMS. Phytochem Anal. 2021 Jul 28. doi: 10.1002/pca.3077. [PubMed:34322910 ]
  3. Wang J, Wei L, Gao G, Zhu J, Su X, Sun L: Comprehensive investigation of pharmacodyamic material basis of Wikstroemia indica (L.) C. A. Mey. by serum pharmacochemistry and bivariate correlation analysis. J Chromatogr B Analyt Technol Biomed Life Sci. 2021 Aug 1;1179:122770. doi: 10.1016/j.jchromb.2021.122770. Epub 2021 Jul 3. [PubMed:34325311 ]
  4. Park J, Lee H, Park K: Gastrointestinal tract and skin permeability of chemicals in consumer products using parallel artificial membrane permeability assay (PAMPA). Environ Anal Health Toxicol. 2021 Sep;36(3):e2021021-0. doi: 10.5620/eaht.2021021. Epub 2021 Sep 27. [PubMed:34583463 ]
  5. Muresan-Pop M, Vulpoi A, Simon V, Todea M, Magyari K, Pap Z, Simion A, Filip C, Simon S: Co-Crystals of Etravirine by Mechanochemical Activation. J Pharm Sci. 2022 Apr;111(4):1178-1186. doi: 10.1016/j.xphs.2021.09.023. Epub 2021 Sep 22. [PubMed:34562446 ]
  6. Kazemzadeh K, Hajj Chehade M, Hourdoir G, Brunet CD, Caspar Y, Loiseau L, Barras F, Pierrel F, Pelosi L: The Biosynthetic Pathway of Ubiquinone Contributes to Pathogenicity of Francisella novicida. J Bacteriol. 2021 Nov 5;203(23):e0040021. doi: 10.1128/JB.00400-21. Epub 2021 Sep 20. [PubMed:34543102 ]
  7. Nathu H, Mbuyama KR, Adarkwah-Yiadom M, Serem JC, Ibrahim MA, Duodu KG, Gaspar ARM, Bester MJ: Antioxidant properties and inhibition of lipid formation in 3T3-L1 adipocytes of in vitro digested mageu, a commercial sample. J Food Biochem. 2021 Oct;45(10):e13929. doi: 10.1111/jfbc.13929. Epub 2021 Sep 14. [PubMed:34519069 ]
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