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Record Information
Version3.6
Creation Date2013-06-12 17:33:01 UTC
Update Date2016-02-11 08:08:00 UTC
HMDB IDHMDB60542
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Hydroxydiclofenac
Description5-Hydroxydiclofenac (5-OH-DCF) is a metabolite of Diclofenac. Diclofenac (cf. INN with trade names) is a nonsteroidal anti-inflammatory drug (NSAID) taken to reduce inflammation and as an analgesic reducing pain in certain conditions. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
2-[(2,6-dichloroanilino)-5-Hydroxyphenyl]acetic acidChEBI
5-Hydroxy diclofenacChEBI
5-OH DCFChEBI
2-[(2,6-dichloroanilino)-5-Hydroxyphenyl]acetateGenerator
Chemical FormulaC14H11Cl2NO3
Average Molecular Weight312.148
Monoisotopic Molecular Weight311.011598637
IUPAC Name2-{2-[(2,6-dichlorophenyl)amino]-5-hydroxyphenyl}acetic acid
Traditional Name5-hydroxydiclofenac
CAS Registry NumberNot Available
SMILES
OC(=O)CC1=CC(O)=CC=C1NC1=C(Cl)C=CC=C1Cl
InChI Identifier
InChI=1S/C14H11Cl2NO3/c15-10-2-1-3-11(16)14(10)17-12-5-4-9(18)6-8(12)7-13(19)20/h1-6,17-18H,7H2,(H,19,20)
InChI KeyInChIKey=VNQURRWYKFZKJZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acid derivatives
Direct ParentPhenylacetic acid derivatives
Alternative Parents
Substituents
  • Phenylacetate
  • Substituted aniline
  • 1,3-dichlorobenzene
  • Aminophenol
  • Phenol
  • Halobenzene
  • Chlorobenzene
  • Aniline
  • Aryl halide
  • Aryl chloride
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.011 mg/mLALOGPS
logP4.27ALOGPS
logP3.96ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)3.81ChemAxon
pKa (Strongest Basic)-0.68ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity77.44 m3·mol-1ChemAxon
Polarizability29.11 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00147
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60542
Metagene LinkHMDB60542
METLIN IDNot Available
PubChem Compound3052566
PDB IDNot Available
ChEBI ID59612
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available