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Record Information
Version3.6
Creation Date2013-07-09 16:05:06 UTC
Update Date2017-08-15 23:27:18 UTC
HMDB IDHMDB0060883
Secondary Accession Numbers
  • HMDB60883
Metabolite Identification
Common Name7-Hydroxy-R-acenocoumarol
Description7-Hydroxy-R-acenocoumarol is a metabolite of acenocoumarol. Acenocoumarol is an anticoagulant that functions as a vitamin K antagonist. It is a derivative of coumarin and is marketed under the brand names Sintrom and Sinthrome. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC19H15NO7
Average Molecular Weight369.3249
Monoisotopic Molecular Weight369.084851839
IUPAC Name4,7-dihydroxy-3-[(1S)-1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one
Traditional Name4,7-dihydroxy-3-[(1S)-1-(4-nitrophenyl)-3-oxobutyl]chromen-2-one
CAS Registry NumberNot Available
SMILES
CC(=O)C[C@@H](C1=CC=C(C=C1)N(=O)=O)C1=C(O)C2=C(OC1=O)C=C(O)C=C2
InChI Identifier
InChI=1S/C19H15NO7/c1-10(21)8-15(11-2-4-12(5-3-11)20(25)26)17-18(23)14-7-6-13(22)9-16(14)27-19(17)24/h2-7,9,15,22-23H,8H2,1H3/t15-/m0/s1
InChI KeyJTCREUDLEYTCAB-HNNXBMFYSA-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
  • Nitrobenzene
  • Nitroaromatic compound
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Organic nitro compound
  • Ketone
  • Lactone
  • C-nitro compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Organic 1,3-dipolar compound
  • Organic oxoazanium
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • 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 Solubility0.023 mg/mLALOGPS
logP2.76ALOGPS
logP2.38ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)5.93ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area129.65 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity96.17 m3·mol-1ChemAxon
Polarizability35.52 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 IDDBMET00037
      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 LinkHMDB0060883
      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