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Record Information
Version4.0
Creation Date2013-07-09 16:05:10 UTC
Update Date2017-09-27 08:43:56 UTC
HMDB IDHMDB0060884
Secondary Accession Numbers
  • HMDB60884
Metabolite Identification
Common Name8-Hydroxy-R-acenocoumarol
Description8-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 Name4,8-dihydroxy-3-[(1S)-1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one
Traditional Name4,8-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(O)=CC=C2
InChI Identifier
InChI=1S/C19H15NO7/c1-10(21)9-14(11-5-7-12(8-6-11)20(25)26)16-17(23)13-3-2-4-15(22)18(13)27-19(16)24/h2-8,14,22-23H,9H2,1H3/t14-/m0/s1
InChI KeyRXFXXWMNPIVMHP-AWEZNQCLSA-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
  • Nitrobenzene
  • Nitroaromatic compound
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Vinylogous acid
  • Heteroaromatic compound
  • Organic nitro compound
  • Ketone
  • Lactone
  • C-nitro compound
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Oxacycle
  • Organic oxoazanium
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic zwitterion
  • 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 Solubility0.025 g/LALOGPS
logP2.74ALOGPS
logP3.03ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)5.53ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area129.65 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity96.17 m³·mol⁻¹ChemAxon
Polarizability35.32 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, Positivesplash10-0006-7559000000-5da59141a751ba19bcf2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0005-4110900000-4499f1c6e73954019301View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0009000000-aa6f43ded3fe745b5600View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ul0-0109000000-211b730d71bb31bd28bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0080-3916000000-f6ad85ba9b5720a94fe5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-0009000000-f0c057dc31a38298f94dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-1409000000-5a4d44d53a26b3e7ee13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7902000000-3d4cfb0fb6759dcb9194View 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 IDDBMET00038
      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