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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:05:20 UTC
Update Date2017-12-07 18:16:30 UTC
HMDB IDHMDB0060887
Secondary Accession Numbers
  • HMDB60887
Metabolite Identification
Common Name8-Hydroxy-R-phenprocoumon
Description8-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 Name4,8-dihydroxy-3-[(1R)-1-phenylpropyl]-2H-chromen-2-one
Traditional Name4,8-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(O)=CC=C2
InChI Identifier
InChI=1S/C18H16O4/c1-2-12(11-7-4-3-5-8-11)15-16(20)13-9-6-10-14(19)17(13)22-18(15)21/h3-10,12,19-20H,2H2,1H3/t12-/m1/s1
InChI KeyDKNXIPNBVAVYAP-GFCCVEGCSA-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-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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 Solubility0.055 g/LALOGPS
logP3.91ALOGPS
logP4.08ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)6.1ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity83.62 m³·mol⁻¹ChemAxon
Polarizability30.84 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-2390000000-09aee55140c1bb1bc5aaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-3205900000-9cafa238cd9361b0b8c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-21275246480ad00f001eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-0290000000-62c096ee1bc23ab39dacView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-4920000000-bef390c5817c96216bbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-2917fe916648da07e049View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-0390000000-77899cd4912323bae659View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05bf-7930000000-c00820276075d051f8bcView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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 IDDBMET00041
      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
      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