(S)-Acenocoumarol

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

What is the (S)-Acenocoumarol?

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

Acenocoumarol is an anticoagulant medication. It is a derivative of coumarin, which belongs in plants such as sweet clover, and is structurally similar to warfarin. Acenocoumarol is used to prevent blood clots from forming, or to prevent existing clots from getting larger. It is also used to treat or prevent venous thromboembolism..

Acenocoumarol works by inhibiting the action of vitamin K. Vitamin K is necessary for the synthesis of clotting factors in the liver. Without vitamin K, the clotting factors are not produced, and clotting cannot occur. Acenocoumarol decreases the production of clotting factors, which leads to a longer clotting time..

Acenocoumarol exists as a tablet, an injection, or a solution for infusion. The tablets are taken orally, usually once a day. The injection is given intramuscularly or intravenously. The infusion is given intravenously over a period of 4 to 8 hours..

Acenocoumarol is a very effective anticoagulant medication. It is important to monitor your blood clotting time closely if you are taking acenocoumarol. You will need to have your blood clotting time checked regularly. If your blood clotting time becomes too long, you may be at risk for bleeding..

Acenocoumarol is a very effective anticoagulant medication, but it is important to monitor your blood clotting time closely if you are taking acenocoumarol. You will need to have your blood clotting time checked regularly. If your blood clotting time becomes too long, you may be at risk for bleeding..

3D structure

Cartesian coordinates

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

2D drawing

 

(S)-Acenocoumarol VABCILAOYCMVPS-HNNXBMFYSA-N chemical compound 2D structure molecule svg
(S)-Acenocoumarol

 

Molecule descriptors

 
IUPAC name4-hydroxy-3-[(1S)-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-/m0/s1
InChI KeyVABCILAOYCMVPS-HNNXBMFYSA-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
  • (-)-Acenocoumarin
  • (S)-(-)-Nicoumalone
  • (S)-Acenocoumarol
  • 2H-1-BENZOPYRAN-2-ONE, 4-HYDROXY-3-((1S)-1-(4-NITROPHENYL)-3-OXOBUTYL)-
  • 2H-1-Benzopyran-2-one, 4-hydroxy-3-(1-(4-nitrophenyl)-3-oxobutyl)-, (S)-
  • 2H-1-Benzopyran-2-one,4-hydroxy-3-[(1S)-1-(4-nitrophenyl)-3-oxobutyl]-
  • 4-hydroxy-3-[(1S)-1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one
  • 4-hydroxy-3-[(1S)-1-(4-nitrophenyl)-3-oxobutyl]chromen-2-one
  • 4O90VF03HV
  • 66556-78-3
  • Acenocoumarol, (S)-
  • Q27124202

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3875999
  • ZINC100015192
  • UNII-4O90VF03HV
  • DTXSID20859299
  • CHEBI:53769
  • SCHEMBL43382

Physico-Chemical properties

IUPAC name4-hydroxy-3-[(1S)-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.