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Record Information
Version3.6
Creation Date2012-04-03 14:10:30 UTC
Update Date2016-02-11 01:27:13 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
Chemical FormulaC7H6O4
Average Molecular Weight154.1201
Monoisotopic Molecular Weight154.02660868
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 KeyInChIKey=UYEMGAFJOZZIFP-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
  • Resorcinol
  • Benzoyl
  • Phenol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
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 QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 436
  • Not Applicable
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. [11959959 ]