Glycerol phenylbutyrate

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

What is the Glycerol phenylbutyrate?

The molecule Glycerol phenylbutyrate presents a molecular formula of C33H38O6 and its IUPAC name is 2,3-bis(4-phenylbutanoyloxy)propyl 4-phenylbutanoate.

Glycerol phenylbutyrate (GPB) is a molecule that is used as a medication. It is a prodrug of phenylbutyrate (PBA), which is a short-chain fatty acid. GPB is used to treat urea cycle disorders..

GPB was first synthesized in the early 1960s. In the 1970s, it was found to be an effective treatment for urea cycle disorders. GPB is metabolized to PBA in the liver. PBA is then excreted in the urine..

GPB is well tolerated and has few side effects. The most common side effect is gastrointestinal upset. GPB exists as a liquid or a powder. It is usually taken three times a day..

GPB is a safe and effective treatment for urea cycle disorders. It is well tolerated and has few side effects..

3D structure

Cartesian coordinates

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

2D drawing

 

Glycerol phenylbutyrate ZSDBFLMJVAGKOU-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Glycerol phenylbutyrate

 

Molecule descriptors

 
IUPAC name2,3-bis(4-phenylbutanoyloxy)propyl 4-phenylbutanoate
InChI codeInChI=1S/C33H38O6/c34-31(22-10-19-27-13-4-1-5-14-27)37-25-30(39-33(36)24-12-21-29-17-8-3-9-18-29)26-38-32(35)23-11-20-28-15-6-2-7-16-28/h1-9,13-18,30H,10-12,19-26H2
InChI KeyZSDBFLMJVAGKOU-UHFFFAOYSA-N
SMILESO=C(CCCc1ccccc1)OCC(COC(=O)CCCc1ccccc1)OC(=O)CCCc1ccccc1

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.

  • 2,3-bis(4-phenylbutanoyloxy)propyl 4-phenylbutanoate
  • 611168-24-2
  • AT33615
  • BENZENEBUTANOIC ACID, 1,2,3-PROPANETRIYL ESTER
  • Benzenebutanoic acid, 1,1',1''-(1,2,3-propanetriyl) ester
  • CS-0017499
  • D10127
  • DB08909
  • GLYCEROL PHENYLBUTYRATE
  • GLYCERYL TRI (4-PHENYLBUTYRATE)
  • GLYCERYL TRI(4-PHENYLBUTYRATE)
  • GT4P
  • Glycerol phenylbutyrate
  • Glycerol phenylbutyrate (USAN)
  • Glycerolphenylbutyrate
  • Glyceryl Tri-4-Phenylbutyrate
  • Glyceryl tri-(4-phenylbutyrate)
  • HPN 100
  • HPN-100
  • HPN-100HPN-100
  • HPN100
  • HY-B2087
  • Propane-1,2,3-triyl tris(4-phenylbutanoate)
  • Q15322709
  • Ravicti
  • TRI(4-PHENYLBUTYRYL)GLYCEROL
  • Tris(4-phenylbutyryl)glycerol
  • ZH6F1VCV7B
  • glycerol-phenylbutyrate
  • s6981

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • UNII-ZH6F1VCV7B
  • DTXSID40210005
  • CHEMBL2105745
  • CHEBI:134745
  • SCHEMBL10102804

Physico-Chemical properties

IUPAC name2,3-bis(4-phenylbutanoyloxy)propyl 4-phenylbutanoate
Molecular formulaC33H38O6
Molecular weight530.651
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity151.54
LogP6.1
Topological polar surface area78.9

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.