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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:05:13 UTC
Update Date2021-09-14 15:43:40 UTC
HMDB IDHMDB0060885
Secondary Accession Numbers
  • HMDB60885
Metabolite Identification
Common Name4'-Hydroxy-R-phenprocoumon
Description4'-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
Data?1563866118
SynonymsNot Available
Chemical FormulaC18H16O4
Average Molecular Weight296.3172
Monoisotopic Molecular Weight296.104859
IUPAC Name4-hydroxy-3-[(1R)-1-(4-hydroxyphenyl)propyl]-2H-chromen-2-one
Traditional Name4-hydroxy-3-[(1R)-1-(4-hydroxyphenyl)propyl]chromen-2-one
CAS Registry NumberNot Available
SMILES
CC[C@H](C1=CC=C(O)C=C1)C1=C(O)C2=CC=CC=C2OC1=O
InChI Identifier
InChI=1S/C18H16O4/c1-2-13(11-7-9-12(19)10-8-11)16-17(20)14-5-3-4-6-15(14)22-18(16)21/h3-10,13,19-20H,2H2,1H3/t13-/m1/s1
InChI KeyZPNYHQZRGWFLST-CYBMUJFWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent4-hydroxycoumarins
Alternative Parents
Substituents
  • 4-hydroxycoumarin
  • Benzopyran
  • 1-benzopyran
  • Phenylpropane
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.03 g/LALOGPS
logP3.89ALOGPS
logP3.43ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)6.24ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity83.62 m³·mol⁻¹ChemAxon
Polarizability30.98 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.14231661259
DarkChem[M-H]-170.04931661259
DeepCCS[M+H]+170.70330932474
DeepCCS[M-H]-168.34530932474
DeepCCS[M-2H]-201.53930932474
DeepCCS[M+Na]+176.79630932474
AllCCS[M+H]+170.032859911
AllCCS[M+H-H2O]+166.332859911
AllCCS[M+NH4]+173.432859911
AllCCS[M+Na]+174.432859911
AllCCS[M-H]-173.532859911
AllCCS[M+Na-2H]-173.032859911
AllCCS[M+HCOO]-172.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4'-Hydroxy-R-phenprocoumonCC[C@H](C1=CC=C(O)C=C1)C1=C(O)C2=CC=CC=C2OC1=O3764.9Standard polar33892256
4'-Hydroxy-R-phenprocoumonCC[C@H](C1=CC=C(O)C=C1)C1=C(O)C2=CC=CC=C2OC1=O2744.8Standard non polar33892256
4'-Hydroxy-R-phenprocoumonCC[C@H](C1=CC=C(O)C=C1)C1=C(O)C2=CC=CC=C2OC1=O2847.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4'-Hydroxy-R-phenprocoumon,1TMS,isomer #1CC[C@H](C1=CC=C(O[Si](C)(C)C)C=C1)C1=C(O)C2=CC=CC=C2OC1=O2683.4Semi standard non polar33892256
4'-Hydroxy-R-phenprocoumon,1TMS,isomer #2CC[C@H](C1=CC=C(O)C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O2801.1Semi standard non polar33892256
4'-Hydroxy-R-phenprocoumon,2TMS,isomer #1CC[C@H](C1=CC=C(O[Si](C)(C)C)C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O2726.3Semi standard non polar33892256
4'-Hydroxy-R-phenprocoumon,1TBDMS,isomer #1CC[C@H](C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1=C(O)C2=CC=CC=C2OC1=O2956.1Semi standard non polar33892256
4'-Hydroxy-R-phenprocoumon,1TBDMS,isomer #2CC[C@H](C1=CC=C(O)C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O3075.4Semi standard non polar33892256
4'-Hydroxy-R-phenprocoumon,2TBDMS,isomer #1CC[C@H](C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O3220.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4'-Hydroxy-R-phenprocoumon GC-MS (Non-derivatized) - 70eV, Positivesplash10-0170-2390000000-f3565c8c09ab643c8ab72017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4'-Hydroxy-R-phenprocoumon GC-MS (2 TMS) - 70eV, Positivesplash10-004i-2023900000-29b0a2e520dc2aa52eeb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4'-Hydroxy-R-phenprocoumon GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-Hydroxy-R-phenprocoumon 10V, Positive-QTOFsplash10-0002-0090000000-58ee5f7fecf1d4d99aa92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-Hydroxy-R-phenprocoumon 20V, Positive-QTOFsplash10-0002-0290000000-ce50a22ebecad5757a0c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-Hydroxy-R-phenprocoumon 40V, Positive-QTOFsplash10-0a4i-1920000000-ac5c06a8f82c6f5213512017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-Hydroxy-R-phenprocoumon 10V, Negative-QTOFsplash10-0002-0090000000-be984d44ce2624c0a2642017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-Hydroxy-R-phenprocoumon 20V, Negative-QTOFsplash10-01ot-0390000000-a65d877dd4869fb47ad02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-Hydroxy-R-phenprocoumon 40V, Negative-QTOFsplash10-054p-7960000000-13f8258e37e2296bef192017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-Hydroxy-R-phenprocoumon 10V, Negative-QTOFsplash10-0002-1090000000-5a115cc056c164a80fae2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-Hydroxy-R-phenprocoumon 20V, Negative-QTOFsplash10-03dj-1790000000-ec6f2771880f0eed67562021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-Hydroxy-R-phenprocoumon 40V, Negative-QTOFsplash10-0006-6920000000-f440038be867263cf89a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-Hydroxy-R-phenprocoumon 10V, Positive-QTOFsplash10-01ot-0790000000-6900b676194b84c2e11f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-Hydroxy-R-phenprocoumon 20V, Positive-QTOFsplash10-01ot-0960000000-2733ce54fcde865aa92e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-Hydroxy-R-phenprocoumon 40V, Positive-QTOFsplash10-00tb-6900000000-83561d5c4fd4647501192021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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 Compound91987768
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available