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Identification
NameEthyl biscoumacetate
Accession NumberDB08794
Typesmall molecule
Groupswithdrawn
Description

Ethyl biscoumacetate is a courmarin that is used as an anticoagulant. It has actions similar to those of Warfarin. (From Martindale, The Extra Pharmacopoeia, 30th ed, p226)

Structure
Thumb
Synonyms
SynonymLanguageCode
PelentanNot AvailableNot Available
TromexanNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
Categories
CAS number548-00-5
WeightAverage: 408.3576
Monoisotopic: 408.084517488
Chemical FormulaC22H16O8
InChI KeySEGSDVUVOWIWFX-UHFFFAOYSA-N
InChI
InChI=1S/C22H16O8/c1-2-28-20(25)15(16-18(23)11-7-3-5-9-13(11)29-21(16)26)17-19(24)12-8-4-6-10-14(12)30-22(17)27/h3-10,15,26-27H,2H2,1H3
IUPAC Name
ethyl 2,2-bis(2-hydroxy-4-oxo-4H-chromen-3-yl)acetate
SMILES
CCOC(=O)C(C1=C(O)OC2=CC=CC=C2C1=O)C1=C(O)OC2=CC=CC=C2C1=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassPhenylpropanoids and Polyketides
ClassCoumarins and Derivatives
SubclassNot Available
Direct parentCoumarins and Derivatives
Alternative parentsChromones; Pyranones and Derivatives; Benzene and Substituted Derivatives; Polyols; Carboxylic Acid Esters; Polyamines; Enolates; Ethers
Substituentspyranone; benzene; pyran; polyol; carboxylic acid ester; enolate; ether; polyamine; carboxylic acid derivative
Classification descriptionThis compound belongs to the 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).
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.937
Blood Brain Barrier + 0.5382
Caco-2 permeable + 0.6023
P-glycoprotein substrate Substrate 0.6415
P-glycoprotein inhibitor I Non-inhibitor 0.7527
P-glycoprotein inhibitor II Non-inhibitor 0.7433
Renal organic cation transporter Non-inhibitor 0.8741
CYP450 2C9 substrate Non-substrate 0.7999
CYP450 2D6 substrate Non-substrate 0.9049
CYP450 3A4 substrate Non-substrate 0.6717
CYP450 1A2 substrate Non-inhibitor 0.6524
CYP450 2C9 substrate Inhibitor 0.8453
CYP450 2D6 substrate Non-inhibitor 0.9562
CYP450 2C19 substrate Inhibitor 0.6966
CYP450 3A4 substrate Non-inhibitor 0.9273
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6137
Ames test Non AMES toxic 0.6498
Carcinogenicity Non-carcinogens 0.9167
Biodegradation Not ready biodegradable 0.7564
Rat acute toxicity 2.7178 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.938
hERG inhibition (predictor II) Non-inhibitor 0.896
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point153-154Rosicky, J.; U.S. Patent 2,482,511; September 20,1949; assigned to Spojene Farmaceuticke Zovody (Czechoslovakia).
water solubility153 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
Predicted Properties
PropertyValueSource
water solubility8.61e-02 g/lALOGPS
logP2.18ALOGPS
logP3.22ChemAxon
logS-3.7ALOGPS
pKa (strongest acidic)7.13ChemAxon
pKa (strongest basic)-5.2ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count7ChemAxon
hydrogen donor count2ChemAxon
polar surface area119.36ChemAxon
rotatable bond count5ChemAxon
refractivity123.2ChemAxon
polarizability39.96ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Rosicky, J.; U.S. Patent 2,482,511; September 20,1949; assigned to Spojene Farmaceuticke Zovody (Czechoslovakia).

General ReferenceNot Available
External Links
ResourceLink
ChemSpider10579
ChEBI231177
ChEMBL
WikipediaEthyl_biscoumacetate
ATC CodesB01AA08
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Enzymes

1. Glutamine synthetase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Glutamine synthetase P15104 Details

References:

  1. Sharaev PN, Bogdanov NG, Sarycheva IK, Zhukova EE: [Allosteric regulation of glucosamine synthetase activity by naphthoquinone derivatives and ethyl ester of di-(4-oxycumarinyl-3)-acetic acid]. Biokhimiia. 1981 Feb;46(2):342-6. Pubmed

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Drug created on October 08, 2010 15:27 / Updated on April 22, 2014 10:47