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Showing metabocard for 3-Hydroxybenzoic acid (HMDB0002466)

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enzymes (3) Show 3 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:54 UTC
Update Date2023-02-21 17:16:25 UTC
HMDB IDHMDB0002466
Secondary Accession Numbers
  • HMDB02466
Metabolite Identification
Common Name3-Hydroxybenzoic acid
Description3-Hydroxybenzoic acid, also known as 3-hydroxybenzoate or 3-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. 3-Hydroxybenzoic acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 3-hydroxybenzoic acid is found, on average, in the highest concentration in american cranberries and beers. 3-hydroxybenzoic acid has also been detected, but not quantified in a few different foods, such as bilberries, citrus, and corns. As well, 3-Hydroxybenzoic Acid can be found in the pineapple fruit. It can also be formed by a Pseudomonas species from 3-Chlorobenzoic acid. 3-Hydroxybenzoic acid is a monohydroxybenzoic acid. 3-Hydroxybenzoic acid can be obtained by the alkali fusion of 3-sulfobenzoic acid between 210-220 °C. 3-Hydroxybenzoic acid is a component of castoreum, the exudate from the castor sacs of the mature North American beaver (Castor canadensis) and the European beaver (Castor fiber), used in perfumery.
Structure
Data?1676999785
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002466 (3-Hydroxybenzoic acid)

3-Hydroxybenzoic acid
  Mrv1652305261923572D          

 10 10  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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   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
  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
  6  7  1  0  0  0  0
  6  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
M  END
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3D MOL for HMDB0002466 (3-Hydroxybenzoic acid)

HMDB0002466
     RDKit          3D
3-Hydroxybenzoic acid
 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.1993   -2.0914   -0.3568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0898   -0.8576   -0.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2065   -0.0751   -0.2699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7755   -0.2728   -0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6338    1.1117    0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6154    1.6700    0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7478    0.8836    0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6029   -0.4860    0.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7742   -1.2683    0.1348 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3663   -1.0723   -0.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7482    0.2300    0.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4758    1.7722    0.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7708    2.7419    0.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7467    1.2930    0.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2046   -1.4256   -0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3004   -2.1535   -0.1504 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
  8  9  1  0
  8 10  2  0
 10  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  9 15  1  0
 10 16  1  0
M  END
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3D SDF for HMDB0002466 (3-Hydroxybenzoic acid)

3-Hydroxybenzoic acid
  Mrv1652305261923572D          

 10 10  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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   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
  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
  6  7  1  0  0  0  0
  6  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
M  END
> <DATABASE_ID>
HMDB0002466

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
IJFXRHURBJZNAO-UHFFFAOYSA-N

> <FORMULA>
C7H6O3

> <MOLECULAR_WEIGHT>
138.122

> <EXACT_MASS>
138.031694053

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.915865293587439

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxybenzoic acid

> <ALOGPS_LOGP>
1.81

> <JCHEM_LOGP>
1.3272634023333332

> <ALOGPS_LOGS>
-1.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.54879634453029

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.844596909709927

> <JCHEM_PKA_STRONGEST_BASIC>
-6.007037034515304

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
35.2951

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0002466 (3-Hydroxybenzoic acid)

HMDB0002466
     RDKit          3D
3-Hydroxybenzoic acid
 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.1993   -2.0914   -0.3568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0898   -0.8576   -0.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2065   -0.0751   -0.2699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7755   -0.2728   -0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6338    1.1117    0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6154    1.6700    0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7478    0.8836    0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6029   -0.4860    0.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7742   -1.2683    0.1348 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3663   -1.0723   -0.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7482    0.2300    0.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4758    1.7722    0.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7708    2.7419    0.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7467    1.2930    0.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2046   -1.4256   -0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3004   -2.1535   -0.1504 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
  8  9  1  0
  8 10  2  0
 10  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  9 15  1  0
 10 16  1  0
M  END
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PDB for HMDB0002466 (3-Hydroxybenzoic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3-Hydroxybenzoic acid                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         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  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+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
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0002466 (3-Hydroxybenzoic acid)

COMPND    HMDB0002466
HETATM    1  O1  UNL     1      -2.199  -2.091  -0.357  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.090  -0.858  -0.242  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.207  -0.075  -0.270  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.776  -0.273  -0.081  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.634   1.112   0.049  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.615   1.670   0.203  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.748   0.884   0.232  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.603  -0.486   0.102  1.00  0.00           C  
HETATM    9  O3  UNL     1       2.774  -1.268   0.135  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.366  -1.072  -0.052  1.00  0.00           C  
HETATM   11  H1  UNL     1      -3.748   0.230   0.510  1.00  0.00           H  
HETATM   12  H2  UNL     1      -1.476   1.772   0.035  1.00  0.00           H  
HETATM   13  H3  UNL     1       0.771   2.742   0.308  1.00  0.00           H  
HETATM   14  H4  UNL     1       2.747   1.293   0.351  1.00  0.00           H  
HETATM   15  H5  UNL     1       3.205  -1.426  -0.772  1.00  0.00           H  
HETATM   16  H6  UNL     1       0.300  -2.153  -0.150  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   14
CONECT    8    9   10   10
CONECT    9   15
CONECT   10   16
END
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SMILES for HMDB0002466 (3-Hydroxybenzoic acid)

OC(=O)C1=CC(O)=CC=C1
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INCHI for HMDB0002466 (3-Hydroxybenzoic acid)

InChI=1S/C7H6O3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8H,(H,9,10)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
3-CarboxyphenolChEBI
m-Hydroxybenzoic acidChEBI
m-Salicylic acidChEBI
m-HydroxybenzoateGenerator
m-SalicylateGenerator
3-HydroxybenzoateGenerator
3-Hydroxybenzoic acid, monosodium saltHMDB
Sodium 3-hydroxybenzoic acidHMDB
3-Hydroxybenzoic acid, copper (2+) (1:1) saltHMDB
3-Hydroxy benzoateHMDB
3-Hydroxy benzoic acidHMDB
Acido m-idrossibenzoicoHMDB
Kyselina 3-hydroxybenzoovaHMDB
m-HbaHMDB
Meta-hydroxybenzoateHMDB
Meta-hydroxybenzoic acidHMDB
3-Hydroxybenzoic acidKEGG
3-Hydroxybenzenecarboxylic acidHMDB
Chemical FormulaC7H6O3
Average Molecular Weight138.122
Monoisotopic Molecular Weight138.031694053
IUPAC Name3-hydroxybenzoic acid
Traditional Name3-hydroxybenzoic acid
CAS Registry Number99-06-9
SMILES
OC(=O)C1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C7H6O3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8H,(H,9,10)
InChI KeyIJFXRHURBJZNAO-UHFFFAOYSA-N
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-4-unsubstituted benzenoid
  • 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
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point202 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.25 mg/mL at 25 °CNot Available
LogP1.50HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available125.399http://allccs.zhulab.cn/database/detail?ID=AllCCS00000304
Predicted Molecular Properties
PropertyValueSource
Water Solubility10.2 g/LALOGPS
logP1.81ALOGPS
logP1.33ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.84ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.3 m³·mol⁻¹ChemAxon
Polarizability12.92 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.58331661259
DarkChem[M-H]-126.70831661259
DeepCCS[M+H]+127.98930932474
DeepCCS[M-H]-124.97330932474
DeepCCS[M-2H]-161.88530932474
DeepCCS[M+Na]+137.24230932474
AllCCS[M+H]+128.732859911
AllCCS[M+H-H2O]+124.032859911
AllCCS[M+NH4]+133.132859911
AllCCS[M+Na]+134.432859911
AllCCS[M-H]-123.132859911
AllCCS[M+Na-2H]-124.732859911
AllCCS[M+HCOO]-126.532859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.61 minutes32390414
Predicted by Siyang on May 30, 20229.8958 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.45 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid64.8 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1151.3 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid340.7 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid105.4 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid215.7 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid125.7 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid358.8 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid360.9 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)111.4 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid739.5 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid288.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid990.2 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid236.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid302.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate509.4 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA225.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water190.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxybenzoic acidOC(=O)C1=CC(O)=CC=C12748.2Standard polar33892256
3-Hydroxybenzoic acidOC(=O)C1=CC(O)=CC=C11374.7Standard non polar33892256
3-Hydroxybenzoic acidOC(=O)C1=CC(O)=CC=C11414.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxybenzoic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC(O)=C11561.6Semi standard non polar33892256
3-Hydroxybenzoic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC=CC(C(=O)O)=C11565.5Semi standard non polar33892256
3-Hydroxybenzoic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC(O[Si](C)(C)C)=C11583.1Semi standard non polar33892256
3-Hydroxybenzoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC(O)=C11816.2Semi standard non polar33892256
3-Hydroxybenzoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC(C(=O)O)=C11791.2Semi standard non polar33892256
3-Hydroxybenzoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C12044.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Hydroxybenzoic acid GC-MS (2 TMS)splash10-00r6-4970000000-64e7f8ae165c16e980cb2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Hydroxybenzoic acid EI-B (Non-derivatized)splash10-000i-9500000000-d9aa814a2f50d1d836f52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Hydroxybenzoic acid EI-B (Non-derivatized)splash10-01b9-0490000000-8dc7d3f9d21b46e65fce2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Hydroxybenzoic acid GC-MS (Non-derivatized)splash10-00r6-4970000000-64e7f8ae165c16e980cb2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Hydroxybenzoic acid GC-EI-TOF (Non-derivatized)splash10-01bc-2970000000-477e1a234b54225b30d52017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxybenzoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-6900000000-5fa59abbf3516f7f1f5d2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxybenzoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00r6-7950000000-6f1a99dee5c832c26f1f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxybenzoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0079-9800000000-3a33a2ce526649dfab2e2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxybenzoic acid LC-ESI-QQ , negative-QTOFsplash10-000i-0900000000-3af4e5d6be21011f52302017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxybenzoic acid LC-ESI-QQ , negative-QTOFsplash10-0006-9200000000-3ab18be5287b6641a69d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxybenzoic acid LC-ESI-QQ , negative-QTOFsplash10-0006-9000000000-0d35a29dba0bb23785162017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxybenzoic acid LC-ESI-QQ , negative-QTOFsplash10-0006-9000000000-7e857f89355a610eeaff2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxybenzoic acid LC-ESI-QQ , negative-QTOFsplash10-0006-9000000000-939e8bb535cf951463462017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxybenzoic acid LC-ESI-ITFT , negative-QTOFsplash10-000l-4900000000-81482c693c488ad8f4c52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxybenzoic acid , negative-QTOFsplash10-0006-9300000000-3ea8e8c9716e4cd850942017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxybenzoic acid 40V, Positive-QTOFsplash10-0v00-9000000000-a7519a6737a56791b32a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxybenzoic acid 20V, Positive-QTOFsplash10-004i-9100000000-f3ee48547af32228569f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxybenzoic acid 40V, Negative-QTOFsplash10-002b-9000000000-91492c478336a09f89be2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxybenzoic acid 10V, Negative-QTOFsplash10-0006-9200000000-d2267887d40d9d3f14212021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxybenzoic acid 10V, Positive-QTOFsplash10-0002-9100000000-a69645e9bb295c644ecb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxybenzoic acid 10V, Positive-QTOFsplash10-0002-9100000000-6b4d7fb8d228954a5f4e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxybenzoic acid 20V, Positive-QTOFsplash10-004i-9000000000-44051ba8922f4aa466372021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxybenzoic acid 40V, Positive-QTOFsplash10-0ufr-9000000000-0d14d8fa47f3fce12bbf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxybenzoic acid 20V, Negative-QTOFsplash10-0006-9000000000-32454e9da3c7f75adb072021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxybenzoic acid 40V, Negative-QTOFsplash10-014i-9000000000-c278e100585f9519c40d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxybenzoic acid 50V, Negative-QTOFsplash10-000l-4900000000-4b5c001da72732066e472021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxybenzoic acid 10V, Negative-QTOFsplash10-0006-9200000000-da1c26e4fbbf500035ee2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxybenzoic acid 10V, Positive-QTOFsplash10-000i-3900000000-8414bbe165f5609620942015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxybenzoic acid 20V, Positive-QTOFsplash10-000f-9400000000-65d56d101aeab33c87bd2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxybenzoic acid 40V, Positive-QTOFsplash10-00kf-9000000000-8e8d3089786e50374c302015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxybenzoic acid 10V, Negative-QTOFsplash10-000i-3900000000-09f6fef5d396e66708ec2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxybenzoic acid 20V, Negative-QTOFsplash10-000f-9500000000-c48f64be4d63def937192015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxybenzoic acid 40V, Negative-QTOFsplash10-0006-9000000000-587072f8cf909dafae1e2015-04-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.089 +/- 0.006 uMAdult (>18 years old)Male
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.273 +/- 1.198 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.089 +/- 0.008 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.09 +/- 0.01 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.194 +/- 0.056 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.149 +/- 0.024 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.103 +/- 0.015 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.119 +/- 0.023 uMAdult (>18 years old)Male
Normal		 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
FecesDetected and Quantified6.878 +/- 3.548 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified0.340 (0.0652-1.260) nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected and Quantified7.530 +/- 9.774 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified4.561 +/- 2.317 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified4.272 +/- 4.416 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
UrineDetected and Quantified0.135 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.00300-2.510 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified1.0 +/- 0.44 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
UrineDetected and Quantified0.121 +/- 0.036 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound ID429
FooDB IDFDB010507
KNApSAcK IDC00040822
Chemspider ID7142
KEGG Compound IDC00587
BioCyc ID3-HYDROXYBENZOATE
BiGG IDNot Available
Wikipedia Link3-Hydroxybenzoic_acid
METLIN ID6690
PubChem Compound7420
PDB IDNot Available
ChEBI ID30764
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceUngnade, H. E.; Henick, A. S. Preparation of m-hydroxybenzoic acid. Journal of the American Chemical Society (1942), 64 1737-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Liu JH, Smith PC: Direct analysis of salicylic acid, salicyl acyl glucuronide, salicyluric acid and gentisic acid in human plasma and urine by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Jan 12;675(1):61-70. [PubMed:8634769 ]
  2. Ito S, Maruta K, Imai Y, Kato T, Ito M, Nakajima S, Fujita K, Kurahashi T: Urinary p-aminobenzoic acid determined in the pancreatic function test by liquid chromatography, with electrochemical detection. Clin Chem. 1982 Feb;28(2):323-6. [PubMed:6976857 ]
  3. Dubois H, Delvoux B, Ehrhardt V, Greiling H: An enzymic assay for uric acid in serum and urine compared with HPLC. J Clin Chem Clin Biochem. 1989 Mar;27(3):151-6. [PubMed:2708944 ]
  4. Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]
  5. http://www.chemicalland21.com/lifescience/phar/m-HYDROXYBENZOIC%20ACID.htm [Link]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
3-Hydroxybenzoic acid → 6-(3-carboxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3-Hydroxybenzoic acid → 3,4,5-trihydroxy-6-(3-hydroxybenzoyloxy)oxane-2-carboxylic aciddetails
Enzyme Details
2. Glycine N-acyltransferase
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
Reactions
3-Hydroxybenzoic acid → 3-Hydroxyhippuric aciddetails
Enzyme Details
3. Sulfotransferase 1A3
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
3-Hydroxybenzoic acid → 3-hydroxybenzoic acid-3-O-sulphatedetails