Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:05:10 UTC
Update Date2021-09-14 15:46:16 UTC
HMDB IDHMDB0060884
Secondary Accession Numbers
  • HMDB60884
Metabolite Identification
Common Name8-Hydroxy-R-acenocoumarol
Description8-Hydroxy-R-acenocoumarol 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. 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. 8-Hydroxy-R-acenocoumarol is an extremely weak basic (essentially neutral) compound (based on its pKa). 8-Hydroxy-R-acenocoumarol is a metabolite of acenocoumarol.
Structure
Data?1563866118
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
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
  • 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
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 Solubility0.025 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
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]+184.79331661259
DarkChem[M-H]-183.13531661259
DeepCCS[M+H]+184.67530932474
DeepCCS[M-H]-182.2830932474
DeepCCS[M-2H]-215.84930932474
DeepCCS[M+Na]+190.9730932474
AllCCS[M+H]+184.432859911
AllCCS[M+H-H2O]+181.332859911
AllCCS[M+NH4]+187.332859911
AllCCS[M+Na]+188.132859911
AllCCS[M-H]-185.732859911
AllCCS[M+Na-2H]-185.332859911
AllCCS[M+HCOO]-185.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8-Hydroxy-R-acenocoumarolCC(=O)C[C@@H](C1=CC=C(C=C1)N(=O)=O)C1=C(O)C2=C(OC1=O)C(O)=CC=C24587.6Standard polar33892256
8-Hydroxy-R-acenocoumarolCC(=O)C[C@@H](C1=CC=C(C=C1)N(=O)=O)C1=C(O)C2=C(OC1=O)C(O)=CC=C21998.7Standard non polar33892256
8-Hydroxy-R-acenocoumarolCC(=O)C[C@@H](C1=CC=C(C=C1)N(=O)=O)C1=C(O)C2=C(OC1=O)C(O)=CC=C23422.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8-Hydroxy-R-acenocoumarol,1TMS,isomer #1CC(=O)C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC(O)=C2OC1=O3320.1Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,1TMS,isomer #2CC(=O)C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=CC(O[Si](C)(C)C)=C2OC1=O3302.3Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,1TMS,isomer #3CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=CC(O)=C2OC1=O)O[Si](C)(C)C3379.2Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,1TMS,isomer #4C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=CC(O)=C2OC1=O)O[Si](C)(C)C3353.3Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,2TMS,isomer #1CC(=O)C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC(O[Si](C)(C)C)=C2OC1=O3344.7Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,2TMS,isomer #2CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC(O)=C2OC1=O)O[Si](C)(C)C3352.6Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,2TMS,isomer #3C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC(O)=C2OC1=O)O[Si](C)(C)C3325.7Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,2TMS,isomer #4CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=CC(O[Si](C)(C)C)=C2OC1=O)O[Si](C)(C)C3363.0Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,2TMS,isomer #5C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=CC(O[Si](C)(C)C)=C2OC1=O)O[Si](C)(C)C3345.5Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,3TMS,isomer #1CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC(O[Si](C)(C)C)=C2OC1=O)O[Si](C)(C)C3393.8Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,3TMS,isomer #1CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC(O[Si](C)(C)C)=C2OC1=O)O[Si](C)(C)C3215.8Standard non polar33892256
8-Hydroxy-R-acenocoumarol,3TMS,isomer #1CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC(O[Si](C)(C)C)=C2OC1=O)O[Si](C)(C)C3713.2Standard polar33892256
8-Hydroxy-R-acenocoumarol,3TMS,isomer #2C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC(O[Si](C)(C)C)=C2OC1=O)O[Si](C)(C)C3368.8Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,3TMS,isomer #2C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC(O[Si](C)(C)C)=C2OC1=O)O[Si](C)(C)C3062.2Standard non polar33892256
8-Hydroxy-R-acenocoumarol,3TMS,isomer #2C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C)C2=CC=CC(O[Si](C)(C)C)=C2OC1=O)O[Si](C)(C)C3713.0Standard polar33892256
8-Hydroxy-R-acenocoumarol,1TBDMS,isomer #1CC(=O)C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC(O)=C2OC1=O3578.6Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,1TBDMS,isomer #2CC(=O)C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2OC1=O3563.0Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,1TBDMS,isomer #3CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=CC(O)=C2OC1=O)O[Si](C)(C)C(C)(C)C3655.0Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,1TBDMS,isomer #4C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=CC(O)=C2OC1=O)O[Si](C)(C)C(C)(C)C3645.5Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,2TBDMS,isomer #1CC(=O)C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2OC1=O3803.9Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,2TBDMS,isomer #2CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC(O)=C2OC1=O)O[Si](C)(C)C(C)(C)C3884.0Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,2TBDMS,isomer #3C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC(O)=C2OC1=O)O[Si](C)(C)C(C)(C)C3853.3Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,2TBDMS,isomer #4CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2OC1=O)O[Si](C)(C)C(C)(C)C3889.8Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,2TBDMS,isomer #5C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2OC1=O)O[Si](C)(C)C(C)(C)C3866.2Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,3TBDMS,isomer #1CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2OC1=O)O[Si](C)(C)C(C)(C)C4113.7Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,3TBDMS,isomer #1CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2OC1=O)O[Si](C)(C)C(C)(C)C3847.3Standard non polar33892256
8-Hydroxy-R-acenocoumarol,3TBDMS,isomer #1CC(=C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2OC1=O)O[Si](C)(C)C(C)(C)C3872.7Standard polar33892256
8-Hydroxy-R-acenocoumarol,3TBDMS,isomer #2C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2OC1=O)O[Si](C)(C)C(C)(C)C4082.4Semi standard non polar33892256
8-Hydroxy-R-acenocoumarol,3TBDMS,isomer #2C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2OC1=O)O[Si](C)(C)C(C)(C)C3652.0Standard non polar33892256
8-Hydroxy-R-acenocoumarol,3TBDMS,isomer #2C=C(C[C@@H](C1=CC=C([N+](=O)[O-])C=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2OC1=O)O[Si](C)(C)C(C)(C)C3879.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxy-R-acenocoumarol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7559000000-5da59141a751ba19bcf22017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxy-R-acenocoumarol GC-MS (2 TMS) - 70eV, Positivesplash10-0005-4110900000-4499f1c6e739540193012017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxy-R-acenocoumarol 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 - 8-Hydroxy-R-acenocoumarol 10V, Positive-QTOFsplash10-0fk9-0009000000-aa6f43ded3fe745b56002017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxy-R-acenocoumarol 20V, Positive-QTOFsplash10-0ul0-0109000000-211b730d71bb31bd28bb2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxy-R-acenocoumarol 40V, Positive-QTOFsplash10-0080-3916000000-f6ad85ba9b5720a94fe52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxy-R-acenocoumarol 10V, Negative-QTOFsplash10-0gb9-0009000000-f0c057dc31a38298f94d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxy-R-acenocoumarol 20V, Negative-QTOFsplash10-00or-1409000000-5a4d44d53a26b3e7ee132017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxy-R-acenocoumarol 40V, Negative-QTOFsplash10-0a4i-7902000000-3d4cfb0fb6759dcb91942017-10-06Wishart 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 Compound131769985
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