Difenacoum (T3D3104)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-07-23 18:26:18 UTC
Update Date2014-12-24 20:25:59 UTC
Accession NumberT3D3104
Identification
Common NameDifenacoum
ClassSmall Molecule
DescriptionDifenacoum is an anticoagulant and rodenticide derived from coumarin. (1)
Compound Type
  • Aromatic Hydrocarbon
  • Ester
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
Difenakum
Diphenacoum
Neosorexa
Neosorexa PP580
Ratak
Chemical FormulaC31H24O3
Average Molecular Mass444.521 g/mol
Monoisotopic Mass444.173 g/mol
CAS Registry Number56073-07-5
IUPAC Name2-hydroxy-3-[3-(4-phenylphenyl)-1,2,3,4-tetrahydronaphthalen-1-yl]-4H-chromen-4-one
Traditional Namedifenacoum
SMILESOC1=C(C2CC(CC3=CC=CC=C23)C2=CC=C(C=C2)C2=CC=CC=C2)C(=O)C2=CC=CC=C2O1
InChI IdentifierInChI=1S/C31H24O3/c32-30-26-12-6-7-13-28(26)34-31(33)29(30)27-19-24(18-23-10-4-5-11-25(23)27)22-16-14-21(15-17-22)20-8-2-1-3-9-20/h1-17,24,27,33H,18-19H2
InChI KeyInChIKey=NZOWVZVFSVRNOR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassPhenylnaphthalenes
Direct ParentPhenylnaphthalenes
Alternative Parents
Substituents
  • Phenylnaphthalene
  • Biphenyl
  • Chromone
  • Coumarin
  • Benzopyran
  • Tetralin
  • 1-benzopyran
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point216°C
Boiling PointNot Available
Solubility3.1e-05 mg/mL at 20°C [TOMLIN,C (1997); pH 5.2]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.6e-05 g/LALOGPS
logP6.92ALOGPS
logP7.63ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)8.19ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity143.79 m³·mol⁻¹ChemAxon
Polarizability50.64 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0010900000-35d204308f797d0f20aa2016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-0692600000-f220e16ee1aa853d438e2016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ba-0942300000-e51d9b04d9e0aa5931f82016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0005-0009700000-16213263bfe60616bcdb2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0309400000-33ec15e8eceb2512fb622016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-5429000000-a9ce2c585f32feebefb52016-08-03View Spectrum
Toxicity Profile
Route of ExposureOral (ingestion) (5) ; dermal (5)
Mechanism of ToxicityDifenacoum inhibits the enzyme Vitamin K epoxide reductase. This enzyme is needed for the reconstitution of the vitamin K in its cycle from vitamin K-epoxide, and so difenacoum steadily decreases the level of active vitamin K in the blood. Vitamin K is required for the synthesis of important substances including prothrombin, which is involved in blood clotting. This disruption becomes increasingly severe until the blood effectively loses any ability to clot. In addition, difenacoum increases permeability of blood capillaries. The blood plasma and blood itself begins to leak from the blood vessels, causing internal bleeding leading to shock, loss of consciousness, and eventually death. (4)
MetabolismNot Available
Toxicity ValuesLD50: 0.8 mg/kg (Oral, Mouse) (2) LD50: 50 mg/kg (Dermal, Rat) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesDifenacoum is a rodenticide. (3)
Minimum Risk LevelNot Available
Health EffectsDifenacoum is an anticoagulant and causes internal bleeding, leading to shock, loss of consciousness, and eventually death. (4)
SymptomsDifenacoum initially causes dehydration before progressing to bleeding complications. (4)
TreatmentThe primary antidote to difenacoum poisoning is immediate administration of vitamin K1 (initially slow intravenous injections of 10-25 mg repeated all 3-6 hours until normalisation of the prothrombin time; then 10 mg orally four times daily as a "maintenance dose"). It is an extremely effective antidote, provided the poisoning is caught before too much damage has been done to the victim's circulatory system. At high doses difenacoum can affect the body for many months, and the antidote must be administered regularly for a long period of time. (4)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID41735
ChEMBL IDNot Available
ChemSpider ID38081
KEGG IDC16807
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDDifenacoum
PDB IDNot Available
ACToR ID15188
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3104.pdf
General References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
  2. Krieger, R (2001). Handbook of Pesticide Toxicology. Volume 2, 2nd ed. San Diego, California: Academic Press.
  3. Wikipedia. Coumarin. Last Updated 21 July 2009. [Link]
  4. Wikipedia. Brodifacoum. Last Updated 22 June 2009. [Link]
  5. Wikipedia. Phytotoxin. Last Updated 7 August 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Vitamin K epoxide reductase complex subunit 1
General Function:
Vitamin-k-epoxide reductase (warfarin-sensitive) activity
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. Vitamin K is required for the gamma-carboxylation of various proteins, including clotting factors, and is required for normal blood coagulation, but also for normal bone development.
Gene Name:
VKORC1
Uniprot ID:
Q9BQB6
Molecular Weight:
18234.3 Da
References
  1. Wikipedia. Brodifacoum. Last Updated 22 June 2009. [Link]