Fumarin (T3D3103)

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 NumberT3D3103
Identification
Common NameFumarin
ClassSmall Molecule
DescriptionFumarin is an anticoagulant and rodenticide derived from coumarin. (3)
Compound Type
  • Aromatic Hydrocarbon
  • Ester
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
3-(1-Furyl-3-acetylethyl)-4-hydroxycoumarin
3-(a-Furyl-b-acetylaethyl)-4-hydroxycumarin
3-(alpha-Acetonyl-2-furylmethyl)-4-hydroxycoumarin
3-(alpha-Acetonylfurfuryl)-4-hydroxycoumarin
3-(alpha-Acetonylfuryl)-4-hydroxy-coumarin
3-(alpha-Furyl-beta-acetylaethyl)-4-hydroxycumarin
3-[1-(2-Furyl)-3-oxobutyl]-4-hydroxy-2H-chromen-2-one
4-(2-Furyl)-4-(4-hydroxy-3-coumarinyl)-2-butanone
4-(2-Furyl)-4-(4-hydroxy-3-kumarinyl)-2-butanon
Coumafuryl
Cumafuryl
Foumarin
Fumasol
Furmarin
Kill-ko rat
Krumkil
Kumatox
Lurat
Mouse blues
Rat-a-way
Ratafin
Tomarin
Chemical FormulaC17H14O5
Average Molecular Mass298.290 g/mol
Monoisotopic Mass298.084 g/mol
CAS Registry Number117-52-2
IUPAC Name3-[1-(furan-2-yl)-3-oxobutyl]-2-hydroxy-4H-chromen-4-one
Traditional Namefumarin
SMILESCC(=O)CC(C1=CC=CO1)C1=C(O)OC2=CC=CC=C2C1=O
InChI IdentifierInChI=1S/C17H14O5/c1-10(18)9-12(13-7-4-8-21-13)15-16(19)11-5-2-3-6-14(11)22-17(15)20/h2-8,12,20H,9H2,1H3
InChI KeyInChIKey=VGVYRHYDNGFIGF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassNot Available
Direct ParentCoumarins and derivatives
Alternative Parents
Substituents
  • Chromone
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Furan
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • 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 Point124°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP2.31ALOGPS
logP2.5ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)7.47ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area76.74 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity88.45 m³·mol⁻¹ChemAxon
Polarizability29.89 ųChemAxon
Number of Rings3ChemAxon
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, Positivesplash10-000t-0090000000-0cd7f2dee8d2f3eca0b62016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-1290000000-3885f4b00eeecf0dc4572016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-4490000000-51e23f1dc99fe4fe53e42016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0090000000-b119a3e79640f86bd3cf2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0nmj-2590000000-9606cfac8f7e649513492016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052o-9650000000-f28b41cceeb5578087592016-08-03View Spectrum
Toxicity Profile
Route of ExposureOral (ingestion) (5) ; dermal (5)
Mechanism of ToxicityFumarin 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 fumarin 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, fumarin 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: 14.7 mg/kg (Oral, Mouse) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFumarin is a rodenticide. (3)
Minimum Risk LevelNot Available
Health EffectsFumarin is an anticoagulant and causes internal bleeding, leading to shock, loss of consciousness, and eventually death. (4)
SymptomsFumarin initially causes dehydration before progressing to bleeding complications. (4)
TreatmentThe primary antidote to fumarin 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 fumarin 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 ID8335
ChEMBL IDNot Available
ChemSpider ID8032
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDFumarin
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3103.pdf
General References
  1. Meijerman I, Beijnen JH, Schellens JH: Herb-drug interactions in oncology: focus on mechanisms of induction. Oncologist. 2006 Jul-Aug;11(7):742-52. [16880233 ]
  2. Farm Chemicals Handbook (2002).Willoughby, OH: Meister Publishing.
  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]