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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:54 UTC
Update Date2018-05-20 20:43:11 UTC
HMDB IDHMDB0002466
Secondary Accession Numbers
  • HMDB02466
Metabolite Identification
Common Name3-Hydroxybenzoic acid
DescriptionProduced in the gut microflora as one of the three main metabolites formed from the catechin diet. Its use in the production of glycol benzoates for the application of plasticizer in adhesive formulations is increasing. It is also used in the manufacture of alkyd resins and drilling mud additive for crude oil recovery applications. It is used as a rubber polymerization activators and retardants.
Structure
Thumb
Synonyms
ValueSource
3-CarboxyphenolChEBI
m-Hydroxybenzoic acidChEBI
m-Salicylic acidChEBI
3-HydroxybenzoateGenerator
m-HydroxybenzoateGenerator
m-SalicylateGenerator
3-Hydroxy benzoateHMDB
3-Hydroxy benzoic acidHMDB
acido m-IdrossibenzoicoHMDB
Kyselina 3-hydroxybenzoovaHMDB
m-HbaHMDB
Meta-hydroxybenzoateHMDB
Meta-hydroxybenzoic acidHMDB
Sodium 3-hydroxybenzoic acidMeSH
3-Hydroxybenzoic acid, copper (2+) (1:1) saltMeSH
3-Hydroxybenzoic acid, monosodium saltMeSH
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
DescriptionThis compound belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. These 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
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental 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)
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00r6-4970000000-64e7f8ae165c16e980cbView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9500000000-d9aa814a2f50d1d836f5View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01b9-0490000000-8dc7d3f9d21b46e65fceView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00r6-4970000000-64e7f8ae165c16e980cbView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01bc-2970000000-477e1a234b54225b30d5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-6900000000-5fa59abbf3516f7f1f5dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00r6-7950000000-6f1a99dee5c832c26f1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-3af4e5d6be21011f5230View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9200000000-3ab18be5287b6641a69dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-0d35a29dba0bb2378516View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-7e857f89355a610eeaffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-939e8bb535cf95146346View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000l-4900000000-81482c693c488ad8f4c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0006-9300000000-3ea8e8c9716e4cd85094View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-3900000000-8414bbe165f560962094View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-9400000000-65d56d101aeab33c87bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-8e8d3089786e50374c30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3900000000-09f6fef5d396e66708ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-9500000000-c48f64be4d63def93719View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-587072f8cf909dafae1eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0079-9800000000-3a33a2ce526649dfab2eView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
BloodDetected and Quantified0.119 +/- 0.023 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.103 +/- 0.015 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.149 +/- 0.024 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.194 +/- 0.056 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.09 +/- 0.01 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.089 +/- 0.006 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.089 +/- 0.008 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified1.273 +/- 1.198 uMAdult (>18 years old)Male
Normal
details
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified4.272 +/- 4.416 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 Quantified6.878 +/- 3.548 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified7.530 +/- 9.774 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Not Specified
    Normal
    details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    FecesDetected and Quantified0.340 (0.0652-1.260) nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 429 details
    UrineDetected and Quantified1,0 +/- 0.44 umol/mmol creatinineAdult (>18 years old)BothNormal 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 Quantified0.121 +/- 0.036 umol/mmol creatinineAdult (>18 years old)Male
    Normal
    details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal 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
    FoodDB IDFDB010507
    KNApSAcK IDC00040822
    Chemspider ID7142
    KEGG Compound IDC00587
    BioCyc ID3-HYDROXYBENZOATE
    BiGG IDNot Available
    Wikipedia Link3-Hydroxybenzoic_acid
    METLIN ID6690
    PubChem Compound7420
    PDB ID3HB
    ChEBI ID30764
    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. http://www.chemicalland21.com/lifescience/phar/m-HYDROXYBENZOIC%20ACID.htm [Link]

    Enzymes

    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
    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
    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