Hmdb loader
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 Date2012-09-06 15:16:51 UTC
Update Date2021-09-14 15:48:00 UTC
HMDB IDHMDB0015257
Secondary Accession Numbers
  • HMDB15257
Metabolite Identification
Common NameAnisindione
DescriptionAnisindione, also known as anisin indandione or miradon, belongs to the class of organic compounds known as indanediones. Indanediones are compounds containing an indane ring bearing two ketone groups. Anisindione is a drug which is used for the prophylaxis and treatment of venous thrombosis and its extension, the treatment of atrial fibrillation with embolization, the prophylaxis and treatment of pulmonary embolism, and as an adjunct in the treatment of coronary occlusion. Anisindione is an extremely weak basic (essentially neutral) compound (based on its pKa). A cyclic beta-diketone consisting of indane-1,3-dione having a 4-methoxyphenyl substituent at the 4-position.
Structure
Data?1582753276
Synonyms
ValueSource
2-(4-Methoxyphenyl)-1H-indene-1,3(2H)-dioneChEBI
2-(4-Methoxyphenyl)indan-1,3-dioneChEBI
2-(p-Methoxyphenyl)-1,3-indandioneChEBI
2-(p-Methoxyphenyl)indane-1,3-dioneChEBI
2-p-Anisyl-1,3-indandioneChEBI
2-Para-anisyl-1,3-indandioneChEBI
Anisin indandioneChEBI
AnisindionaChEBI
AnisindionumChEBI
MiradonKegg
Chemical FormulaC16H12O3
Average Molecular Weight252.2647
Monoisotopic Molecular Weight252.07864425
IUPAC Name2-(4-methoxyphenyl)-2,3-dihydro-1H-indene-1,3-dione
Traditional Nameanisindione
CAS Registry Number117-37-3
SMILES
COC1=CC=C(C=C1)C1C(=O)C2=CC=CC=C2C1=O
InChI Identifier
InChI=1S/C16H12O3/c1-19-11-8-6-10(7-9-11)14-15(17)12-4-2-3-5-13(12)16(14)18/h2-9,14H,1H3
InChI KeyXRCFXMGQEVUZFC-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
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol ether
  • Alkyl aryl ether
  • 1,3-diketone
  • Monocyclic benzene moiety
  • 1,3-dicarbonyl compound
  • Ketone
  • Ether
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point156.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.013 g/LNot Available
LogP2.6Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP10(2.99) g/LALOGPS
logP10(2.72) g/LChemAxon
logS10(-4.3) g/LALOGPS
pKa (Strongest Acidic)4.5ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity71.7 m³·mol⁻¹ChemAxon
Polarizability26.3 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]+159.36931661259
DarkChem[M-H]-158.75131661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AnisindioneCOC1=CC=C(C=C1)C1C(=O)C2=CC=CC=C2C1=O3579.0Standard polar33892256
AnisindioneCOC1=CC=C(C=C1)C1C(=O)C2=CC=CC=C2C1=O2305.5Standard non polar33892256
AnisindioneCOC1=CC=C(C=C1)C1C(=O)C2=CC=CC=C2C1=O2321.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Anisindione GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pi0-2970000000-3072f4dff3d83d6798e02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anisindione 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 - Anisindione 10V, Positive-QTOFsplash10-0udi-0090000000-9a00a2012741ee8d529d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisindione 20V, Positive-QTOFsplash10-0udi-0290000000-ae6d022536ede61e9a682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisindione 40V, Positive-QTOFsplash10-0zfr-5970000000-697cb6e17075d45c94f82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisindione 10V, Negative-QTOFsplash10-0udi-0090000000-1e24bd40cb0266b810592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisindione 20V, Negative-QTOFsplash10-0udi-0090000000-db4a7df8621482e26e272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisindione 40V, Negative-QTOFsplash10-000i-1490000000-17630a8bb2f337db9f2c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisindione 10V, Positive-QTOFsplash10-0udi-0090000000-8d91e33e4298322ba53d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisindione 20V, Positive-QTOFsplash10-0udi-0690000000-5f01d86cb0ff3819b6082021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisindione 40V, Positive-QTOFsplash10-004i-9510000000-c5661b94b65978419e912021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisindione 10V, Negative-QTOFsplash10-0udi-0090000000-aedd17caff57899b7eff2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisindione 20V, Negative-QTOFsplash10-0udi-0090000000-de3608db6e681e51eb8b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisindione 40V, Negative-QTOFsplash10-0532-0940000000-2d549322c6ad1c2373b42021-10-11Wishart LabView Spectrum
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 DB01125 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01125 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01125
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2112
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAnisindione
METLIN IDNot Available
PubChem Compound2197
PDB IDNot Available
ChEBI ID133809
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. CONNELL WF, MAYER GA: Evaluation of anticoagulant therapy with anisindione (miradon). Can Med Assoc J. 1959 May 15;80(10):785-90. [PubMed:13652026 ]

Enzymes

General function:
Involved in gamma-glutamyl carboxylase activity
Specific function:
Mediates the vitamin K-dependent carboxylation of glutamate residues to calcium-binding gamma-carboxyglutamate (Gla) residues with the concomitant conversion of the reduced hydroquinone form of vitamin K to vitamin K epoxide.
Gene Name:
GGCX
Uniprot ID:
P38435
Molecular weight:
87560.065
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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]