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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2016-02-11 01:32:05 UTC
HMDB IDHMDB15257
Secondary Accession NumbersNone
Metabolite Identification
Common NameAnisindione
DescriptionAnisindione is a synthetic anticoagulant and an indanedione derivative. It prevents the formation of active procoagulation factors II, VII, IX, and X, as well as the anticoagulant proteins C and S, in the liver by inhibiting the vitamin K-mediated gamma-carboxylation of precursor proteins.
Structure
Thumb
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
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 KeyInChIKey=XRCFXMGQEVUZFC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indanones. These are compounds containing an indane ring bearing a ketone group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassIndanes
Sub ClassIndanones
Direct ParentIndanones
Alternative Parents
Substituents
  • Indanone
  • Indanedione
  • Methoxybenzene
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol ether
  • Anisole
  • 1,3-diketone
  • Alkyl aryl ether
  • 1,3-dicarbonyl compound
  • Monocyclic benzene moiety
  • Ketone
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anticoagulants
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point156.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.28e-02 g/LNot Available
LogP2.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.013 mg/mLALOGPS
logP2.99ALOGPS
logP2.72ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.5ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity71.7 m3·mol-1ChemAxon
Polarizability26.3 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01125
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01125
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01125
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2112
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAnisindione
NuGOwiki LinkHMDB15257
Metagene LinkHMDB15257
METLIN IDNot Available
PubChem Compound2197
PDB IDNot Available
ChEBI ID133809
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. [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. [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. [17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]