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Record Information
Version3.6
Creation Date2012-04-03 14:10:30 UTC
Update Date2017-03-02 21:33:00 UTC
HMDB IDHMDB13677
Secondary Accession NumbersNone
Metabolite Identification
Common Name3,5-Dihydroxybenzoic acid
Description3,5-dihydroxybenzoic acid is a primary metabolite of alkylresinols which has been hydrolyzed by liver enzymes during phase I metabolism after several cycles of beta oxidation.
Structure
Thumb
Synonyms
ValueSource
alpha-Resorcylic acidChEBI
a-ResorcylateGenerator
a-Resorcylic acidGenerator
alpha-ResorcylateGenerator
α-resorcylateGenerator
α-resorcylic acidGenerator
3,5-DihydroxybenzoateGenerator
3,5-Dihydroxy-benzoic acidHMDB
3,5-Dihydroxybenzoic acid (acd/name 4.0)HMDB
5-CarboxyresorcinolHMDB
BenzoateHMDB
Benzoic acidHMDB
alpha-Resorcylic acid, copper (2+) saltMeSH
alpha-Resorcylic acid, sodium saltMeSH
Chemical FormulaC7H6O4
Average Molecular Weight154.121
Monoisotopic Molecular Weight154.026608673
IUPAC Name3,5-dihydroxybenzoic acid
Traditional Name3,5-dihydroxybenzoic acid
CAS Registry Number99-10-5
SMILES
OC(=O)C1=CC(O)=CC(O)=C1
InChI Identifier
InChI=1S/C7H6O4/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3,8-9H,(H,10,11)
InChI KeyUYEMGAFJOZZIFP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Hydroxybenzoic acid
  • Benzoic acid
  • Resorcinol
  • 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
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point237 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.86Not Available
Predicted Properties
PropertyValueSource
Water Solubility12.0 mg/mLALOGPS
logP1.29ALOGPS
logP1.02ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.28 m3·mol-1ChemAxon
Polarizability13.88 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    BloodDetected and Quantified0.091 +/- 0.029 uMAdult (>18 years old)Male
    Normal
    details
    BloodDetected and Quantified0.035 +/- 0.019 uMAdult (>18 years old)Male
    Normal
    details
    BloodDetected and Quantified0.069 +/- 0.028 uMAdult (>18 years old)Male
    Normal
    details
    BloodDetected and Quantified0.297 +/- 0.185 uMAdult (>18 years old)Male
    Normal
    details
    BloodDetected and Quantified0.065 +/- 0.024 uMAdult (>18 years old)Male
    Normal
    details
    BloodDetected and Quantified0.101 +/- 0.045 uMAdult (>18 years old)Male
    Normal
    details
    BloodDetected and Quantified0.066 +/- 0.03 uMAdult (>18 years old)Male
    Normal
    details
    BloodDetected and Quantified0.4 +/- 0.268 uMAdult (>18 years old)Male
    Normal
    details
    FecesDetected and Quantified1.168 +/- 0.843 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified1.168 +/- 1.363 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified1.363 +/- 1.0382 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified2.271 +/- 1.363 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 436 details
    UrineDetected and Quantified0.218 +/- 0.124 umol/mmol creatinineAdult (>18 years old)Male
    Normal
    details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound ID436
    Phenol Explorer Metabolite ID436
    FoodDB IDFDB000848
    KNApSAcK IDC00016318
    Chemspider ID7146
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia Link3,5-dihydroxybenzoic_acid
    NuGOwiki LinkHMDB13677
    Metagene LinkHMDB13677
    METLIN IDNot Available
    PubChem Compound7424
    PDB ID34D
    ChEBI ID258254
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Elemans JA, Boerakker MJ, Holder SJ, Rowan AE, Cho WD, Percec V, Nolte RJ: Plastic- and liquid-crystalline architectures from dendritic receptor molecules. Proc Natl Acad Sci U S A. 2002 Apr 16;99(8):5093-8. [PubMed:11959959 ]