Showing metabocard for 4-Hydroxybenzoic acid (MMDBc0000519)

Plant
Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:39:37 UTC
Update Date2022-08-31 06:07:55 UTC
Metabolite IDMMDBc0000519
Metabolite 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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f1240f8c6a0>


  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
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3D MOL for #<Metabolite:0x00007f1240f8c6a0>

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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3D SDF for #<Metabolite:0x00007f1240f8c6a0>


  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>
MMDBc0000519

> <DATABASE_NAME>
MIME

> <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

$$$$
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3D-SDF for #<Metabolite:0x00007f1240f8c6a0>

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 #<Metabolite:0x00007f1240f8c6a0>

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 #<Metabolite:0x00007f1240f8c6a0>

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 #<Metabolite:0x00007f1240f8c6a0>

OC(=O)C1=CC=C(O)C=C1
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INCHI for #<Metabolite:0x00007f1240f8c6a0>

InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)
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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
4-Hydroxybenzoic acidHMDB
Molecular FormulaC7H6O3
Average Mass138.122
Monoisotopic Mass138.031694053
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