4'-Hydroxy-R-phenprocoumon

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for 4'-Hydroxy-R-phenprocoumon are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the 4'-Hydroxy-R-phenprocoumon?

The molecule 4'-Hydroxy-R-phenprocoumon presents a molecular formula of C18H16O4 and its IUPAC name is 4-hydroxy-3-[(1R)-1-(4-hydroxyphenyl)propyl]chromen-2-one.

Phenprocoumon is an anticoagulant medication. It is a coumarin derivative and acts by inhibiting vitamin K epoxide reductase. This enzyme is responsible for the regeneration of active vitamin K, which is essential for the formation of clotting factors II, VII, IX, and X. Phenprocoumon is used to prevent thromboembolic events such as stroke and heart attack. It is also used to treat atrial fibrillation and other heart conditions. The usual dose is 100-200 mg once daily. Phenprocoumon exists in tablets, capsules, and injectable forms..

3D structure

Cartesian coordinates

Geometry of 4'-Hydroxy-R-phenprocoumon in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

4'-Hydroxy-R-phenprocoumon ZPNYHQZRGWFLST-CYBMUJFWSA-N chemical compound 2D structure molecule svg
4'-Hydroxy-R-phenprocoumon

 

Molecule descriptors

 
IUPAC name4-hydroxy-3-[(1R)-1-(4-hydroxyphenyl)propyl]chromen-2-one
InChI codeInChI=1S/C18H16O4/c1-2-13(11-7-9-12(19)10-8-11)16-17(20)14-5-3-4-6-15(14)22-18(16)21/h3-10,13,19-20H,2H2,1H3/t13-/m1/s1
InChI KeyZPNYHQZRGWFLST-CYBMUJFWSA-N
SMILESCC[C@H](c1ccc(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-[(1R)-1-(4-Hydroxyphenyl)propyl]-4-hydroxycoumarin
  • 4'-Hydroxy-R-phenprocoumon
  • 4-HYDROXY-3-[(1R)-1-(4-HYDROXYPHENYL)PROPYL]CHROMEN-2-ONE

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC5599377
  • CHEBI:174814

Physico-Chemical properties

IUPAC name4-hydroxy-3-[(1R)-1-(4-hydroxyphenyl)propyl]chromen-2-one
Molecular formulaC18H16O4
Molecular weight296.317
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity85.60
LogP3.7
Topological polar surface area70.7

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.