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Showing NP-Card for 4-Hydroxybenzoic acid (NP0001074)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-02-10 01:53:29 UTC
NP-MRD IDNP0001074
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Hydroxybenzoic acid
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 is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. It is a nutty and phenolic tasting compound. 4-Hydroxybenzoic acid exists in all living species, ranging from bacteria to plants to humans. 4-Hydroxybenzoic acid can be found naturally in coconut. It is one of the main catechins metabolites found in humans after consumption of green tea infusions. It is also found in wine, in vanilla, in Açaí oil, obtained from the fruit of the açaí palm (Euterpe oleracea), at relatively high concetrations (892±52 mg/kg). It is also found in cloudy olive oil and in the edible mushroom Russula virescens. It has been detected in red huckleberries, rabbiteye blueberries, and corianders and in a lower concentration in olives, red raspberries, and almonds. In humans, 4-hydroxybenzoic acid is involved in ubiquinone biosynthesis. In particular, the enzyme 4-hydroxybenzoate polyprenyltransferase uses a polyprenyl diphosphate and 4-hydroxybenzoate to produce diphosphate and 4-hydroxy-3-polyprenylbenzoate. This enzyme participates in ubiquinone biosynthesis. 4-Hydroxybenzoic acid can be biosynthesized by the enzyme Chorismate lyase. Chorismate lyase is an enzyme that transforms chorismate into 4-hydroxybenzoate and pyruvate. This enzyme catalyses the first step in ubiquinone biosynthesis in Escherichia coli and other Gram-negative bacteria. 4-Hydroxybenzoate is an intermediate in many enzyme-mediated reactions in microbes. For instance, the enzyme 4-hydroxybenzaldehyde dehydrogenase uses 4-hydroxybenzaldehyde, NAD+ and H2O to produce 4-hydroxybenzoate, NADH and H+. This enzyme participates in toluene and xylene degradation in bacteria such as Pseudomonas mendocina. 4-Hydroxybenzaldehyde dehydrogenase is also found in carrots. The enzyme 4-hydroxybenzoate 1-hydroxylase transforms 4-hydroxybenzoate, NAD(P)H, 2 H+ and O2 into hydroquinone, NAD(P)+, H2O and CO2. This enzyme participates in 2,4-dichlorobenzoate degradation and is found in Candida parapsilosis. The enzyme 4-hydroxybenzoate 3-monooxygenase transforms 4-hydroxybenzoate, NADPH, H+ and O2 into protocatechuate, NADP+ and H2O. This enzyme participates in benzoate degradation via hydroxylation and 2,4-dichlorobenzoate degradation and is found in Pseudomonas putida and Pseudomonas fluorescens. 4-Hydroxybenzoic acid is a popular antioxidant in part because of its low toxicity. 4-Hydroxybenzoic acid has estrogenic activity both in vitro and in vivo (PMID 9417843 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001074 (4-Hydroxybenzoic acid)


  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 NP0001074 (4-Hydroxybenzoic acid)

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 NP0001074 (4-Hydroxybenzoic acid)


  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>
NP0001074

> <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 NP0001074 (4-Hydroxybenzoic acid)

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
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PDB for NP0001074 (4-Hydroxybenzoic acid)

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
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3D PDB for NP0001074 (4-Hydroxybenzoic acid)

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 NP0001074 (4-Hydroxybenzoic acid)

OC(=O)C1=CC=C(O)C=C1
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INCHI for NP0001074 (4-Hydroxybenzoic acid)

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 Number99-96-7
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, 700 MHz, H2O, simulated)Ahselim2022-02-10View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-02-10View 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
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abeliophyllum distichumLOTUS Database
Abutilon indicumPlant
Acacia catechuPlant
Achlys triphyllaLOTUS Database
Aconitum japonicumLOTUS Database
Adenostoma fasciculatumLOTUS Database
Adenostoma sparsifoliumLOTUS Database
Aegle marmelosPlant
Aeschynanthus bracteatusKNApSAcK Database
Ailanthus altissimaLOTUS Database
Allium cepaFooDB
Allium chinenseLOTUS Database
Allium fistulosumLOTUS Database
Allium sativumKNApSAcK Database
Aloe africanaLOTUS Database
Althaea cannabinaLOTUS Database
Althaea officinalisLOTUS Database
Ammothamnus lehmanniiLOTUS Database
Amphibolis antarcticaKNApSAcK Database
Amphibolis griffithiiKNApSAcK Database
Anacardium occidentaleKNApSAcK Database
Anadenanthera colubrinaLOTUS Database
Anaphalis lacteaLOTUS Database
Anas platyrhynchosFooDB
Anastatica hierochunticaLOTUS Database
AnatidaeFooDB
Andrographis paniculataLOTUS Database
Anethum graveolensFooDB
Anigozanthos preissiiLOTUS Database
Anisomeles indicaKNApSAcK Database
Annona cherimolaLOTUS Database
Anser anserFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arbutus unedoLOTUS Database
Ardisia virensLOTUS Database
Areca catechuKNApSAcK Database
Aristolochia cucurbitifoliaLOTUS Database
Aristolochia elegansKNApSAcK Database
Aristolochia kaempferiLOTUS Database
Aristolochia manshuriensisKNApSAcK Database
Armoracia rusticanaFooDB
Artemisia absinthiumLOTUS Database
Artemisia dracunculusFooDB
Artemisia minorKNApSAcK Database
Artocarpus heterophyllusLOTUS Database
Aspalathus linearisLOTUS Database
Asperula odorataLOTUS Database
Aster indicusLOTUS Database
Astragalus onobrychisLOTUS Database
Astragalus wagneriLOTUS Database
Athyrium yokoscenseLOTUS Database
Avena fatuaLOTUS Database
Avena sativaLOTUS Database
Avena sativa L.FooDB
Bacopa monnieriLOTUS Database
Begonia nantoensisKNApSAcK Database
Berchemia racemosaLOTUS Database
Beta vulgarisLOTUS Database
Beta vulgaris ssp. ciclaFooDB
Betula pendulaLOTUS Database
Betula pubescensLOTUS Database
Bison bisonFooDB
Bletilla striataLOTUS Database
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica napusLOTUS Database
Brassica oleracea L. ssp. BotrytisKNApSAcK Database
Brassica oleracea var. gongylodesKNApSAcK Database
Brassica oleracea var. italicaFooDB
Bubalus bubalisFooDB
Cajanus cajanFooDB
Calliandra haematocephalaLOTUS Database
Camellia japonicaLOTUS Database
Camellia sinensisLOTUS Database
Campanula lactifloraLOTUS Database
Canarium schweinfurthiiLOTUS Database
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
Carduus tenuiflorusLOTUS Database
Carya cathayensisLOTUS Database
Castanea sativaLOTUS Database
Casuarina equisetifoliaLOTUS Database
Catalpa bignonioidesKNApSAcK Database
Catharanthus roseusPlant
Centaurea asperaLOTUS Database
Centaurea pallescensLOTUS Database
Centaurea polypodiifoliaLOTUS Database
Centaurea regiaLOTUS Database
CervidaeFooDB
Cervus canadensisFooDB
Cestrum parquiLOTUS Database
Chelidonium majusLOTUS Database
Chlamydomonas reinhardtiiLOTUS Database
Chrysanthemum segetumLOTUS Database
Chrysanthemum zawadskiiLOTUS Database
Cicer arietinumFooDB
Cichorium intybusFooDB
Cinnamomum reticulatumLOTUS Database
Cinnamomum subaveniumPlant
Cinnamomum subavenium MIQ.KNApSAcK Database
Cinnamomum yabunikkeiLOTUS Database
Citrullus colocynthisPlant
Citrus aurantiumLOTUS Database
Citrus paradisiFooDB
Citrus sinensisLOTUS Database
Clausena excavataLOTUS Database
Cocculus laurifoliusLOTUS Database
Cocos nuciferaKNApSAcK Database
Codiaeum variegatumLOTUS Database
Codonopsis pilosulaLOTUS Database
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colchicum kotschyiLOTUS Database
Colubrina faralaotra subsp.trichocarpa.KNApSAcK Database
ColumbaFooDB
ColumbidaeFooDB
Conyza canadensisKNApSAcK Database
Corchorus olitoriusLOTUS Database
Cordia macleodiiKNApSAcK Database
Coriandrum sativumLOTUS Database
Coriandrum sativum L.FooDB
Corylus americanaLOTUS Database
Cowania mexicanaKNApSAcK Database
Crataegus monogynaLOTUS Database
Crepis pontanaLOTUS Database
Crinum asiaticumLOTUS Database
Crocus sativusLOTUS Database
Cucumis meloFooDB
Cucumis sativusLOTUS Database
Cullen corylifoliumLOTUS Database
Cuminum cyminumFooDB
Curcuma domesticaKNApSAcK Database
Curcuma longaPlant
Cymodocea rotundataKNApSAcK Database
Cymodocea serrulataKNApSAcK Database
Cynomorium songaricumLOTUS Database
Cyperus rotundusPlant
Cyperus rotundus L.KNApSAcK Database
Cytospora ceratospermaLOTUS Database
Daphne odoraLOTUS Database
Daucus carotaKNApSAcK Database
Daucus carota ssp. sativusFooDB
    • Adrian J. Parr, Annie Ng, and Keith W. Waldron Ester-Linked Phenolic Components of Carrot Cell Wa...
Delphinium elatumLOTUS Database
Delphinium venulosumLOTUS Database
Dendrobium falconeriLOTUS Database
Dianthus longicalyxLOTUS Database
Dianthus superbusLOTUS Database
Dianthus superbus var.longicalycinus (MAXIM.) WILLKNApSAcK Database
Diospyros lotusLOTUS Database
Dipteryx odorataLOTUS Database
Dittrichia graveolensLOTUS Database
Dromaius novaehollandiaeFooDB
Drymaria cordataPlant
Drymaria diandraKNApSAcK Database
Duhaldea cappaLOTUS Database
Echinacea purpureaLOTUS Database
Elaeis guineensisKNApSAcK Database
Elettaria cardamomumFooDB
Eleusine coracanaLOTUS Database
Eleutherococcus senticosusLOTUS Database
Enhalus acoroidesKNApSAcK Database
Ephedra aphyllaKNApSAcK Database
Ephedra equisetinaKNApSAcK Database
Epichloe typhinaLOTUS Database
Equisetum arvenseLOTUS Database
Equisetum ramosissimumLOTUS Database
Equsetum arvense-
Equus caballusFooDB
Erigeron breviscapusLOTUS Database
Erigeron canadensisPlant
Eriobotrya japonicaFooDB
Ervatamia coronariaLOTUS Database
Erythrina sigmoideaLOTUS Database
Eucalyptus camaldulensisLOTUS Database
Euchresta formosanaLOTUS Database
Euodia fargesiiLOTUS Database
Euphorbia aleppicaLOTUS Database
Euphorbia lagascaeLOTUS Database
Euterpe precatoriaKNApSAcK Database
Excoecaria cochinchinensisLOTUS Database
Fagara macrophyllaKNApSAcK Database
Fagopyrum esculentumFooDB
Falcaria vulgarisKNApSAcK Database
Festuca rubraLOTUS Database
Ficaria vernaLOTUS Database
Ficus septicaLOTUS Database
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Galinsoga quadriradiataLOTUS Database
Gallus gallusFooDB
Gaultheria itoanaLOTUS Database
Gaultheria procumbensLOTUS Database
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Gliricidia sepiumLOTUS Database
Glycine maxFooDB
Glycyrrhiza uralensisLOTUS Database
Gnetum parvifoliumLOTUS Database
Gomphrena celosioidesKNApSAcK Database
Grangea maderaspatanaLOTUS Database
Grosmannia crassivaginataLOTUS Database
Guanomyces polythrixLOTUS Database
Gymnadenia conopseaLOTUS Database
Gymnadenia conopsea R.BR.KNApSAcK Database
Gynura japonicaLOTUS Database
Hagenia abyssinicaLOTUS Database
Halimodendron halodendronLOTUS Database
Halodule uninervisKNApSAcK Database
Halodule wrightiiKNApSAcK Database
Halophila engelmanniiKNApSAcK Database
Halophila hawaiianaKNApSAcK Database
Halophila minorKNApSAcK Database
Handroanthus impetiginosusPlant
Haplopteris anguste-elongataLOTUS Database
Helianthus annuus L.FooDB
Hibiscus taiwanensisKNApSAcK Database
Hippophae rhamnoidesFooDB
Homo sapiensLOTUS Database
Hordeum vulgareFooDB
Hornstedtia reticulataLOTUS Database
Houttuynia cordataLOTUS Database
Humulus lupulusKNApSAcK Database
Hydrangea chinensisKNApSAcK Database
Hypericum hirsutumLOTUS Database
Hypericum laricifoliumLOTUS Database
Hyssopus officinalis L.FooDB
Ilex dunnianaLOTUS Database
Impatiens balsaminaLOTUS Database
Imperata cylindricaLOTUS Database
Iris domesticaLOTUS Database
Iris ensataLOTUS Database
Isatis tinctoriaLOTUS Database
Juglans nigra L.FooDB
Jurinea deltoideaLOTUS Database
Kalanchoe delagoensisLOTUS Database
Kalanchoe pinnataLOTUS Database
Lagenaria brevifloraLOTUS Database
Lagerstroemia speciosaLOTUS Database
Lagopus mutaFooDB
Lantana trifoliaLOTUS Database
Larix laricinaLOTUS Database
Larix sibiricaLOTUS Database
Lens culinarisFooDB
LeporidaeFooDB
Lepus timidusFooDB
Lindera glaucaLOTUS Database
Linum austriacum subsp.glaucescensPlant
Linum hirsutum subsp.anatolicumPlant
Linum tenuifoliumPlant
Linum usitatissimumFooDB
Liriodendron tulipiferaLOTUS Database
Lithospermum erythrorhizonKNApSAcK Database
Litsea hypophaeaLOTUS Database
Lonicera microphyllaLOTUS Database
Lotus corniculatusLOTUS Database
Lotus uliginosusLOTUS Database
Lupinus angustifoliusLOTUS Database
Lycopus europaeusLOTUS Database
Maclura cochinchinensisLOTUS Database
Magnolia denudataKNApSAcK Database
Magnolia liliifloraKNApSAcK Database
Malus pumilaFooDB
Malus sylvestrisLOTUS Database
Malva silvestrisKNApSAcK Database
Mangifera indicaKNApSAcK Database
Maranta arundinaceaFooDB
Marasmiellus ramealisLOTUS Database
Matricaria chamomillaKNApSAcK Database
Matricaria recutitaFooDB
Matteuccia struthiopterisLOTUS Database
Maytenus loevisKNApSAcK Database
Medicago sativaKNApSAcK Database
Melaleuca ericifoliaLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melilotus messanensisKNApSAcK Database
Melissa officinalis L.FooDB
Mentha spicataFooDB
Menyanthes trifoliataLOTUS Database
Mespilus germanicaKNApSAcK Database
Michelia albaLOTUS Database
Michelia compressaLOTUS Database
Microtropis fokienensisKNApSAcK Database
Momordica charantiaKNApSAcK Database
Monascus pilosusLOTUS Database
Moringa oleiferaLOTUS Database
Murraya euchrestifoliaLOTUS Database
Murraya paniculataLOTUS Database
Nelumbo nuciferaLOTUS Database
Nigella glanduliferaLOTUS Database
Numida meleagrisFooDB
Nymphaea albaLOTUS Database
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Oenothera grandifloraLOTUS Database
Olea europaeaFooDB
Onobrychis arenariaLOTUS Database
Ononis speciosaLOTUS Database
Ophiocordyceps sinensisLOTUS Database
Opunitia dillenii HAW.-
Opuntia dilleniiLOTUS Database
Opuntia strictaLOTUS Database
Origanum majoranaFooDB
Origanum vulgareFooDB
OryctolagusFooDB
Oryza sativaFooDB
Osyris albaLOTUS Database
Ovis ariesFooDB
Oxalis corniculataKNApSAcK Database
Oxalis pes-capraeLOTUS Database
Paeonia emodiLOTUS Database
Paeonia lactifloraLOTUS Database
Paeonia obovataLOTUS Database
Paeonia peregrinaKNApSAcK Database
Paeonia suffruticosaLOTUS Database
Panax ginsengLOTUS Database
Pandanus amaryllifoliusLOTUS Database
Pandanus odorusKNApSAcK Database
Papaver somniferumLOTUS Database
Paratecoma perobaKNApSAcK Database
Pelargonium reniformeKNApSAcK Database
Penicillium javanicumLOTUS Database
Peperomia heyneanaLOTUS Database
Persea americanaLOTUS Database
Persicaria hydropiperLOTUS Database
Petasites formosanusLOTUS Database
Petroselinum crispumFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phellodendron amurenseKNApSAcK Database
Phellodendron japonicum MAXIMKNApSAcK Database
Phoenix dactyliferaFooDB
Phoenx canariensis-
Phyllospadix scouleriKNApSAcK Database
Phyllospadix serrulatusKNApSAcK Database
Phyllospadix torreyiKNApSAcK Database
Picea ajanensisKNApSAcK Database
Picea glaucaLOTUS Database
Picea jezoensis var. jezoensisPlant
Picea koraiensisLOTUS Database
Picea obovataKNApSAcK Database
Pimpinella anisumFooDB
Pinus densifloraLOTUS Database
Pinus roxburghiiKNApSAcK Database
Pinus sylvestrisLOTUS Database
Pisum sativumFooDB
Plantago lanceolataKNApSAcK Database
Plantago majorLOTUS Database
Plantago mediaKNApSAcK Database
Polyalthia longifolia var.pendulaKNApSAcK Database
Polygala caudataKNApSAcK Database
Polygonum cognatumLOTUS Database
Polygonum convolvulusLOTUS Database
Polytrichum communeKNApSAcK Database
Populus deltoidesLOTUS Database
Populus euphraticaLOTUS Database
Populus pseudosimoniiKNApSAcK Database
Populus tremulaLOTUS Database
Posidonia australisKNApSAcK Database
Posidonia oceanicaKNApSAcK Database
Premna fulvaLOTUS Database
Protea obtusifoliaKNApSAcK Database
Prunus aviumKNApSAcK Database
Prunus cerasusFooDB
Prunus domesticaLOTUS Database
Prunus dulcisFooDB
Pterocarpus santalinusKNApSAcK Database
Pyrus communisFooDB
Pyrus kawakamiiLOTUS Database
Ranunculus baudotiiKNApSAcK Database
Ranunculus chinensisLOTUS Database
Reseda muricataLOTUS Database
Reseda muricata C.Presl.KNApSAcK Database
Rhaponticum carthamoidesKNApSAcK Database
Rhodiola crenulataLOTUS Database
Rhodiola sacraLOTUS Database
Rhododendron dauricumLOTUS Database
Ribes nigrumLOTUS Database
Ribes rubrumFooDB
Richardia brasiliensisLOTUS Database
Richardia grandifloraLOTUS Database
Rodgersia sambucifoliaLOTUS Database
Rorippa indicaLOTUS Database
Rorippa sylvestrisLOTUS Database
Rosmarinus officinalisKNApSAcK Database
Roystonea regiaKNApSAcK Database
Rubus idaeusFooDB
Rubus spectabilisFooDB
Rumex japonicusLOTUS Database
Rumex thyrsiflorusPlant
Salix atrocinereaLOTUS Database
Salsola collinaLOTUS Database
Salvia divaricataLOTUS Database
Salvia moorcroftianaLOTUS Database
Salvia officinalisKNApSAcK Database
Salvia rosmarinusFooDB
Sarcolaeana multiflora-
Sargentodoxa cuneataLOTUS Database
Saussurea muliensisKNApSAcK Database
Scrophularia frutescensLOTUS Database
Scrophularia nodosaLOTUS Database
Scrophularis sambucifolia-
Secale cerealeFooDB
Secamone afzeliiLOTUS Database
Silphium perfoliatumLOTUS Database
Solanum lycopersicumLOTUS Database
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum tuberosumKNApSAcK Database
Solidago canadensisLOTUS Database
Sophora pachycarpaLOTUS Database
Sorghum halepenseLOTUS Database
Soymida febrifugaKNApSAcK Database
Spathodea campanulataLOTUS Database
Spiraea formosanaKNApSAcK Database
Strelitzia reginaeKNApSAcK Database
Streptomyces xanthophaeusLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syagrus romanzoffianaLOTUS Database
Synechococcus elongatusLOTUS Database
Synsepalum dulcificumLOTUS Database
Syringodium filiformeKNApSAcK Database
Syringodium isoetifoliumKNApSAcK Database
Tabebuia avellanedaeKNApSAcK Database
Tabebuia impetiginosaKNApSAcK Database
Talipariti tiliaceumLOTUS Database
Taraxacum formosanumKNApSAcK Database
Taraxacum mongolicumLOTUS Database
Taxus baccataKNApSAcK Database
Terminalia catappaPlant
Terminalia chebulaPlant
Terminalia nigrovenulosaPlant
Thalassia ciliatumKNApSAcK Database
Thalassia hemprichiiKNApSAcK Database
Thalassia testudinumKNApSAcK Database
Thalassodendron ciliatumKNApSAcK Database
Theobroma cacaoFooDB
Thymus vulgarisFooDB
Toona ciliataKNApSAcK Database
Tragopogon pratensisLOTUS Database
Tribulus terrestrisKNApSAcK Database
Trichilia monadelphaLOTUS Database
Trifolium pratensePlant
Tristaniopsis calobuxusLOTUS Database
Triticum aestivumKNApSAcK Database
Triticum turgidumLOTUS Database
Tsuga chinensisLOTUS Database
Typha orientalisKNApSAcK Database
Ulva lactuca-
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumLOTUS Database
Vaccinium uliginosumFooDB
Valeriana amurensisLOTUS Database
Vanilla planifolia Jacks.LOTUS Database
Vanilla pomponaLOTUS Database
Vanilla x tahitensisLOTUS Database
Veronica americanaPlant
Veronica didymaPlant
Veronica montanaPlant
Veronica persicaLOTUS Database
Veronica spuriaPlant
Viburnum cylindricumLOTUS Database
Viburnum dilatatumLOTUS Database
Vicia fabaFooDB
Vigna radiataFooDB
Vigna unguiculataFooDB
Viscum articulactumKNApSAcK Database
Viscum articulatumLOTUS Database
Viscum coloratumKNApSAcK Database
Visnea mocaneraLOTUS Database
Vitex agnus-castusLOTUS Database
Vitex negundoKNApSAcK Database
Vitex polygamaKNApSAcK Database
Vitex trifoliaLOTUS Database
Vitis viniferaKNApSAcK Database
Vitis vinifera L.FooDB
Vittaria anguste-elongataKNApSAcK Database
Waitea circinataLOTUS Database
Xanthophyllum rubescensKNApSAcK Database
Xanthophylum rubescens-
Xylocarpus granatumKNApSAcK Database
Zanthoxylum ailanthoidesLOTUS Database
Zanthoxylum beecheyanumLOTUS Database
Zanthoxylum lemaireiLOTUS Database
Zataria multifloraLOTUS Database
Zea mays L.FooDB
Zingiber officinaleFooDB
Ziziphus mauritianaLOTUS Database
Zostera capricorniKNApSAcK Database
Zostera marinaKNApSAcK Database
Zostera muelleriKNApSAcK Database
Zostera noltiiKNApSAcK Database
Zostera tasmanicaKNApSAcK Database
Zyzzya fuliginosa-
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
Monascus pilosus BCRC38072KNApSAcK Database
Pseudomonas putidaKNApSAcK Database
Thelephora aurantiotinctaKNApSAcK 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
  • 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
StateSolid
Experimental Properties
PropertyValueReference
Melting Point213.00 to 215.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point334.00 to 335.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility5 mg/mLNot Available
LogP1.58Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility11.9 g/LALOGPS
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. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  2. Soni MG, Taylor SL, Greenberg NA, Burdock GA: Evaluation of the health aspects of methyl paraben: a review of the published literature. Food Chem Toxicol. 2002 Oct;40(10):1335-73. [PubMed:12387298 ]
  3. Shibusawa H, Sano Y, Yamamoto T, Kambegawa A, Ohkawa T, Satoh N, Okinaga S, Arai K: A radioimmunoassay of serum 16alpha-hydroxypregnenolone with specific antiserum. Endocrinol Jpn. 1978 Apr;25(2):185-9. [PubMed:668632 ]
  4. Wiebe LI, Mercer JR, Ryan AJ: Urinary metabolites of 3,5-di-(1-[13C]methyl-1-methylethyl)4-hydroxytoluene (BHT-13C) in man. Drug Metab Dispos. 1978 May-Jun;6(3):296-302. [PubMed:26551 ]
  5. Sakurai M, Ohsako M, Nagano M, Nakamura C, Tsuzuki O, Ichikawa M, Matsumoto Y: [Effect of human serum albumin on transport of drugs through human erythrocyte membranes]. Yakugaku Zasshi. 1996 Aug;116(8):630-8. [PubMed:8831264 ]
  6. Soni MG, Burdock GA, Taylor SL, Greenberg NA: Safety assessment of propyl paraben: a review of the published literature. Food Chem Toxicol. 2001 Jun;39(6):513-32. [PubMed:11346481 ]
  7. Lemini C, Silva G, Timossi C, Luque D, Valverde A, Gonzalez-Martinez M, Hernandez A, Rubio-Poo C, Chavez Lara B, Valenzuela F: Estrogenic effects of p-hydroxybenzoic acid in CD1 mice. Environ Res. 1997 Nov;75(2):130-4. doi: 10.1006/enrs.1997.3782. [PubMed:9417843 ]
  8. Elsbaey M, Ibrahim MAA, Bar FA, Elgazar AA: Chemical constituents from coconut waste and their in silico evaluation as potential antiviral agents against SARS-CoV-2. S Afr J Bot. 2021 Sep;141:278-289. doi: 10.1016/j.sajb.2021.05.018. Epub 2021 May 28. [PubMed:34092840 ]