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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:05:24 UTC
Update Date2017-10-23 19:15:49 UTC
HMDB IDHMDB0060888
Secondary Accession Numbers
  • HMDB60888
Metabolite Identification
Common Name7-Hydroxy-R-phenprocoumon
Description7-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 Name4,7-dihydroxy-3-[(1R)-1-phenylpropyl]-2H-chromen-2-one
Traditional Name4,7-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=C(O)C=C2
InChI Identifier
InChI=1S/C18H16O4/c1-2-13(11-6-4-3-5-7-11)16-17(20)14-9-8-12(19)10-15(14)22-18(16)21/h3-10,13,19-20H,2H2,1H3/t13-/m1/s1
InChI KeyHBAPGROFUGJSGR-CYBMUJFWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassCoumarins and derivatives
Direct Parent7-hydroxycoumarins
Alternative Parents
Substituents
  • 4-hydroxycoumarin
  • 7-hydroxycoumarin
  • Benzopyran
  • 1-benzopyran
  • Phenylpropane
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • 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
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 Solubility0.036 g/LALOGPS
logP3.88ALOGPS
logP3.43ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)6.47ChemAxon
pKa (Strongest Basic)-6.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity83.62 m³·mol⁻¹ChemAxon
Polarizability31 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-cc07a8409e965b68db3cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-2103900000-9968a8f16540174d2045View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-864da96a3b7d6c2a50a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-0290000000-8457289485725248570cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-009i-3940000000-660948ab1065fcf91d9fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-55e18041aed88c8a9d38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-0390000000-de2bae6cbeccbbbe683eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-062c-5940000000-49b6987512c82ade7f4aView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 IDDBMET00042
      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