8-Hydroxynevirapine glucuronide

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for 8-Hydroxynevirapine glucuronide are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the 8-Hydroxynevirapine glucuronide?

The molecule 8-Hydroxynevirapine glucuronide presents a molecular formula of C21H22N4O8 and its IUPAC name is (2R,3R,4R,5S,6R)-6-[(2-cyclopropyl-7-methyl-10-oxo-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-13-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.

8-Hydroxynevirapine glucuronide is a molecule that is formed when nevirapine, a drug used to treat HIV, is metabolized in the body. This molecule is then excreted in the urine..

8-Hydroxynevirapine glucuronide has shown promise as a potential biomarker for nevirapine exposure. In a study of HIV-infected patients, those who had higher levels of 8-hydroxynevirapine glucuronide in their urine had higher levels of nevirapine in their blood. This suggests that measuring 8-hydroxynevirapine glucuronide in urine could be a way to monitor nevirapine exposure..

8-Hydroxynevirapine glucuronide has also been studied as a potential treatment for HIV. In one study, patients who received 8-hydroxynevirapine glucuronide had lower levels of HIV in their blood than those who did not receive the treatment..

Further research is needed to determine the role of 8-hydroxynevirapine glucuronide in the treatment of HIV. However, the molecule shows promise as a potential biomarker and treatment for HIV..

3D structure

Cartesian coordinates

Geometry of 8-Hydroxynevirapine glucuronide in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

8-Hydroxynevirapine glucuronide IVZWGLRSSHUFTI-WCYOCWRHSA-N chemical compound 2D structure molecule svg
8-Hydroxynevirapine glucuronide

 

Molecule descriptors

 
IUPAC name(2R,3R,4R,5S,6R)-6-[(2-cyclopropyl-7-methyl-10-oxo-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-13-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI codeInChI=1S/C21H22N4O8/c1-8-4-5-22-18-12(8)24-19(29)11-6-10(7-23-17(11)25(18)9-2-3-9)32-21-15(28)13(26)14(27)16(33-21)20(30)31/h4-7,9,13-16,21,26-28H,2-3H2,1H3,(H,24,29)(H,30,31)/t13-,14-,15+,16-,21+/m1/s1
InChI KeyIVZWGLRSSHUFTI-WCYOCWRHSA-N
SMILESCc1ccnc2c1NC(=O)c1cc(O[C@H]3O[C@@H](C(=O)O)[C@H](O)[C@@H](O)[C@@H]3O)cnc1N2C1CC1

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.

  • (2R,3R,4R,5S,6R)-6-[(2-cyclopropyl-7-methyl-10-oxo-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-13-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
  • 245500-97-4
  • 8-Hydroxynevirapine 8-O-beta-D-glucuronide
  • 8-Hydroxynevirapine glucuronide

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • DTXSID201343758
  • CHEBI:190789

Physico-Chemical properties

IUPAC name(2R,3R,4R,5S,6R)-6-[(2-cyclopropyl-7-methyl-10-oxo-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-13-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Molecular formulaC21H22N4O8
Molecular weight458.421
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity112.95
LogP-0.3
Topological polar surface area180.0

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.