(R)-Acenocoumarol

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for (R)-Acenocoumarol are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the (R)-Acenocoumarol?

The molecule (R)-Acenocoumarol presents a molecular formula of C19H15NO6 and its IUPAC name is 4-hydroxy-3-[(1R)-1-(4-nitrophenyl)-3-oxobutyl]chromen-2-one.

Acenocoumarol is an anticoagulant medication. It is a stereoisomer of warfarin, and has a similar mechanism of action. Acenocoumarol is used to treat and prevent venous thromboembolism. It is also used to reduce the risk of stroke in people with atrial fibrillation. Acenocoumarol exists as a generic medication..

The (R)-acenocoumarol molecule has a molecular weight of 325.43 g/mol and a molecular formula of C19H16N2O3S. The molecule is soluble in water and has a pKa of 3.8..

Acenocoumarol inhibits the vitamin K epoxide reductase enzyme, which is responsible for the reduction of vitamin K1 and vitamin K2. This results in the inhibition of the synthesis of coagulation factors II, VII, IX, and X..

Acenocoumarol is metabolized in the liver by the cytochrome P450 enzyme system. The main metabolites are 7-hydroxyacenocoumarol and 3-hydroxyacenocoumarol. These metabolites are further conjugated with glucuronic acid and are excreted in the urine..

The half-life of acenocoumarol is about 24 hours. The therapeutic range is 2-5 ng/mL..

Acenocoumarol is contraindicated in people with a history of hypersensitivity to the drug. It is also contraindicated in people with active bleeding or a history of bleeding disorders..

The most common side effects of acenocoumarol are gastrointestinal bleeding, skin rash, and pruritus. More serious side effects include hemorrhagic stroke, hepatotoxicity, and bone marrow suppression..

Acenocoumarol should be used with caution in people with liver disease, kidney disease, and diabetes. The drug should be used with caution in people of Asian descent because they are more likely to have a genetic predisposition to bleeding..

Acenocoumarol is a pregnancy category C drug. It should be used with caution in pregnant women and only if the potential benefit justifies the potential risk to the fetus..

Acenocoumarol is a prescription medication and should be used as directed by a healthcare provider..

3D structure

Cartesian coordinates

Geometry of (R)-Acenocoumarol in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

(R)-Acenocoumarol VABCILAOYCMVPS-OAHLLOKOSA-N chemical compound 2D structure molecule svg
(R)-Acenocoumarol

 

Molecule descriptors

 
IUPAC name4-hydroxy-3-[(1R)-1-(4-nitrophenyl)-3-oxobutyl]chromen-2-one
InChI codeInChI=1S/C19H15NO6/c1-11(21)10-15(12-6-8-13(9-7-12)20(24)25)17-18(22)14-4-2-3-5-16(14)26-19(17)23/h2-9,15,22H,10H2,1H3/t15-/m1/s1
InChI KeyVABCILAOYCMVPS-OAHLLOKOSA-N
SMILESCC(=O)C[C@H](c1ccc([N+](=O)[O-])cc1)c1c(O)c2ccccc2oc1=O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (+)-3-(.ALPHA.-ACETONYL-4-NITROBENZYL)-4-HYDROXYCOUMARIN
  • (+)-ACENOCOUMAROL
  • (+)-Acenocoumarin
  • (R)-(+)-Acenocoumarol
  • (R)-(+)-Nicoumalone
  • (R)-Acenocoumarol
  • 2-Hydroxy-3-((1R)-1-(4-nitrophenyl)-3-oxo-butyl)chromen-4-one
  • 2H-1-BENZOPYRAN-2-ONE, 4-HYDROXY-3-((1R)-1-(4-NITROPHENYL)-3-OXOBUTYL)-
  • 4-hydroxy-3-[(1R)-1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one
  • 4-hydroxy-3-[(1R)-1-(4-nitrophenyl)-3-oxobutyl]chromen-2-one
  • 66556-77-2
  • Acenocoumarol, (R)-
  • JRD7912W79
  • NCGC00016414-01
  • Q27124201

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3876000
  • ZINC100015190
  • CAS-152-72-7
  • UNII-JRD7912W79
  • DTXSID10873368
  • CHEMBL1317231
  • CHEBI:53768

Physico-Chemical properties

IUPAC name4-hydroxy-3-[(1R)-1-(4-nitrophenyl)-3-oxobutyl]chromen-2-one
Molecular formulaC19H15NO6
Molecular weight353.325
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity97.40
LogP4.0
Topological polar surface area113.3

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.