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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:41 UTC
HMDB IDHMDB0014641
Secondary Accession Numbers
  • HMDB14641
Metabolite Identification
Common NamePhenindione
DescriptionPhenindione is only found in individuals that have used or taken this drug. It is an indandione that has been used as an anticoagulant. Phenindione has actions similar to warfarin, but it is now rarely employed because of its higher incidence of severe adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p234)Phenindione inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). As vitamin K is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent proteins, this limits the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulant proteins. The synthesis of vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S is inhibited. Depression of three of the four vitamin K-dependent coagulation factors (factors II, VII, and X) results in decreased prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots.
Structure
Data?1582753202
Synonyms
ValueSource
2-Phenyl-1,3(2H)-indenedioneChEBI
2-Phenyl-1,3-diketohydrindeneChEBI
2-Phenyl-1,3-indandioneChEBI
FenindionaChEBI
PhenindionumChEBI
PIDChEBI
HedulinKegg
Merck lipha santé brand OF phenindioneHMDB
2 Phenyl 1,3 indandioneHMDB
Boots brand OF phenindioneHMDB
Goldshield brand OF phenindioneHMDB
PhenylindanedioneHMDB
PhenylineHMDB
PindioneHMDB
DindevanHMDB
FenilinHMDB
Chemical FormulaC15H10O2
Average Molecular Weight222.2387
Monoisotopic Molecular Weight222.068079564
IUPAC Name2-phenyl-2,3-dihydro-1H-indene-1,3-dione
Traditional Nameindon
CAS Registry Number83-12-5
SMILES
O=C1C(C(=O)C2=CC=CC=C12)C1=CC=CC=C1
InChI Identifier
InChI=1S/C15H10O2/c16-14-11-8-4-5-9-12(11)15(17)13(14)10-6-2-1-3-7-10/h1-9,13H
InChI KeyNFBAXHOPROOJAW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indanediones. Indanediones are compounds containing an indane ring bearing two ketone groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassIndanes
Sub ClassIndanones
Direct ParentIndanediones
Alternative Parents
Substituents
  • Indanedione
  • Aryl alkyl ketone
  • Aryl ketone
  • 1,3-diketone
  • 1,3-dicarbonyl compound
  • Monocyclic benzene moiety
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point148 - 151 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.023 g/LNot Available
LogP2.6Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available145.917http://allccs.zhulab.cn/database/detail?ID=AllCCS00000760
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.023 g/LALOGPS
logP3.1ALOGPS
logP2.88ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.88ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity65.23 m³·mol⁻¹ChemAxon
Polarizability23.24 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+149.70231661259
DarkChem[M-H]-150.06531661259
DeepCCS[M-2H]-185.83230932474
DeepCCS[M+Na]+161.36330932474
AllCCS[M+H]+149.332859911
AllCCS[M+H-H2O]+145.132859911
AllCCS[M+NH4]+153.232859911
AllCCS[M+Na]+154.432859911
AllCCS[M-H]-152.632859911
AllCCS[M+Na-2H]-151.932859911
AllCCS[M+HCOO]-151.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PhenindioneO=C1C(C(=O)C2=CC=CC=C12)C1=CC=CC=C13201.9Standard polar33892256
PhenindioneO=C1C(C(=O)C2=CC=CC=C12)C1=CC=CC=C12019.5Standard non polar33892256
PhenindioneO=C1C(C(=O)C2=CC=CC=C12)C1=CC=CC=C12069.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phenindione GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-8950000000-db616a8e7e559a5a5f6f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenindione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenindione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-4690000000-3b0da30c88d7d0ecf3392014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenindione 10V, Positive-QTOFsplash10-00di-0090000000-9b298f1072fd790bda042016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenindione 20V, Positive-QTOFsplash10-00di-3390000000-11fefa0e023507256e682016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenindione 40V, Positive-QTOFsplash10-0a4l-9460000000-25e9eb850e8f08d732842016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenindione 10V, Negative-QTOFsplash10-00di-0090000000-3ff702d3fba3b4ba61c92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenindione 20V, Negative-QTOFsplash10-00di-0090000000-782f754ab0024fcab9232016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenindione 40V, Negative-QTOFsplash10-0gi9-5940000000-5905bd66b8f78a2f70a32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenindione 10V, Positive-QTOFsplash10-00di-0090000000-4526ea1529fb7968e1f92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenindione 20V, Positive-QTOFsplash10-00di-2390000000-dafe0249a10821f9782f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenindione 40V, Positive-QTOFsplash10-0006-9100000000-ee672ba3244610e83f292021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenindione 10V, Negative-QTOFsplash10-00di-0090000000-67222288c14ba81150ce2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenindione 20V, Negative-QTOFsplash10-00di-0090000000-67222288c14ba81150ce2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenindione 40V, Negative-QTOFsplash10-01c0-0920000000-f427c2360b8ee97f9d002021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00498 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00498 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00498
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4596
KEGG Compound IDC07584
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenindione
METLIN IDNot Available
PubChem Compound4760
PDB IDNot Available
ChEBI ID8066
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 References
  1. Patient.co.uk [Link]

Enzymes

General function:
Involved in vitamin-K-epoxide reductase (warfarin-sensi
Specific function:
Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K.
Gene Name:
VKORC1
Uniprot ID:
Q9BQB6
Molecular weight:
18234.3
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Mentre F, Pousset F, Comets E, Plaud B, Diquet B, Montalescot G, Ankri A, Mallet A, Lechat P: Population pharmacokinetic-pharmacodynamic analysis of fluindione in patients. Clin Pharmacol Ther. 1998 Jan;63(1):64-78. [PubMed:9465843 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]