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Record Information
Version3.6
Creation Date2013-07-09 16:05:17 UTC
Update Date2017-08-15 23:27:18 UTC
HMDB IDHMDB0060886
Secondary Accession Numbers
  • HMDB60886
Metabolite Identification
Common Name6-Hydroxy-R-phenprocoumon
Description6-Hydroxy-R-phenprocoumon is a metabolite of phenprocoumon. Phenprocoumon (marketed under the brand names Marcoumar, Marcumar and Falithrom) is an anticoagulant drug, a derivative of coumarin. It is a vitamin K antagonist that inhibits coagulation by blocking synthesis of coagulation factors II, VII, IX and X. It is used for the prophylaxis and treatment of thromboembolic disorders. Phenprocoumon is a 4-hydroxycoumarin and inhibits inhibits vitamin K epoxide reductase. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC18H16O4
Average Molecular Weight296.3172
Monoisotopic Molecular Weight296.104859
IUPAC Name4,6-dihydroxy-3-[(1R)-1-phenylpropyl]-2H-chromen-2-one
Traditional Name4,6-dihydroxy-3-[(1R)-1-phenylpropyl]chromen-2-one
CAS Registry NumberNot Available
SMILES
CC[C@H](C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC(O)=C2
InChI Identifier
InChI=1S/C18H16O4/c1-2-13(11-6-4-3-5-7-11)16-17(20)14-10-12(19)8-9-15(14)22-18(16)21/h3-10,13,19-20H,2H2,1H3/t13-/m1/s1
InChI KeyBKRXPRMCBOAGQH-CYBMUJFWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassCoumarins and derivatives
Direct Parent4-hydroxycoumarins
Alternative Parents
Substituents
  • 4-hydroxycoumarin
  • Benzopyran
  • 1-benzopyran
  • Phenylpropane
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.036 mg/mLALOGPS
logP3.86ALOGPS
logP3.43ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)6.04ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity83.62 m3·mol-1ChemAxon
Polarizability31.02 Å3ChemAxon
Number of Rings3ChemAxon
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 Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00040
      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 LinkHMDB0060886
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available