Acarbosa

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

What is the Acarbosa?

The molecule Acarbosa presents a molecular formula of C25H43NO18 and its IUPAC name is (2R,3R,4R,5R)-4-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino]oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal.

Abacavir is a medication used in the treatment of HIV, the virus that causes AIDS. It belongs to a class of drugs known as nucleoside reverse transcriptase inhibitors (NRTIs), which work by inhibiting the activity of the enzyme reverse transcriptase, a key enzyme involved in the replication of HIV..

Abacavir was first approved by the US Food and Drug Administration (FDA) in 1998 and is now widely used in combination with other antiretroviral medications to treat HIV. It is typically prescribed in the form of a once-daily oral tablet, although it is also available as a liquid solution for patients who have difficulty swallowing pills..

Like all medications, abacavir can cause side effects, the most serious of which is a hypersensitivity reaction that occurs in some people who are genetically predisposed to it. This reaction can cause symptoms such as fever, rash, and difficulty breathing, and can be life-threatening if not treated promptly. For this reason, it is important for patients taking abacavir to be monitored closely for any signs of a hypersensitivity reaction..

In addition to its use in the treatment of HIV, abacavir has also been studied for its potential use in the treatment of other viral infections, including hepatitis B and influenza. However, further research is needed to fully understand the safety and effectiveness of abacavir for these conditions..

Summary

From all the above, this molecule is a medication used in the treatment of HIV. It works by inhibiting the activity of the enzyme reverse transcriptase, which is necessary for the replication of the virus. While it is generally well-tolerated, it can cause serious side effects in some people, and it is important for patients taking abacavir to be monitored closely for any signs of a hypersensitivity reaction..

3D structure

Cartesian coordinates

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

2D drawing

 

Acarbosa CEMXHAPUFJOOSV-XGWNLRGSSA-N chemical compound 2D structure molecule svg
Acarbosa

 

Molecule descriptors

 
IUPAC name(2R,3R,4R,5R)-4-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino]oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal
InChI codeInChI=1S/C25H43NO18/c1-7-13(26-9-2-8(3-27)14(33)18(37)15(9)34)17(36)20(39)24(41-7)44-23-12(6-30)42-25(21(40)19(23)38)43-22(11(32)5-29)16(35)10(31)4-28/h2,4,7,9-27,29-40H,3,5-6H2,1H3/t7-,9+,10+,11-,12-,13-,14-,15+,16-,17+,18+,19-,20-,21-,22-,23-,24-,25-/m1/s1
InChI KeyCEMXHAPUFJOOSV-XGWNLRGSSA-N
SMILESC[C@H]1O[C@H](O[C@@H]2[C@@H](CO)O[C@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1N[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O

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,5R)-4-(((2R,3R,4R,5S,6R)-5-(((2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-(((1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl)amino)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2,3,5,6-tetrahydroxyhexanal
  • Acarbosa
  • BAYG5421
  • BIDD:GT0622
  • CS-1787
  • D-GLUCOSE, O-4,6-DIDEOXY-4-(((1S-(1.ALPHA.,4.ALPHA.,5.BETA.,6.ALPHA.))-4,5,6-TRIHYDROXY-3-(HYDROXYMETHYL)-2-CYCLOHEXEN-1-YL)AMINO)-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-
  • D-Glucose, O-4,6-dideoxy-4-(((1S-(1-alpha,4-alpha,5-beta,6-alpha))-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-alpha-D-glucopyranosyl-(1-4)-O-alpha-D-glucopyranosyl-(1-4)-
  • D-Glucose, O-4,6-dideoxy-4-(((1S-(1alpha,4alpha,5beta,6alpha))-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-alpha-D-glucopyranosyl-(1-4)-O-alpha-D-glucopyranosyl-(1-4)-
  • DB00284
  • DS-3277
  • HSDB 7984
  • HY-B0089
  • NSC 758915
  • O-4,6-DIDEOXY-4-(((1S,4R,5S,6S)-4,5,6-TRIHYDROXY-3-(HYDROXYMETHYL)-2-CYCLOHEXEN-1-YL)AMINO)-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-D-GLUCOSE
  • O-4,6-DIDEOXY-4-(((1S,4R,5S,6S)-4,5,6-TRIHYDROXY-3-(HYDROXYMETHYL)-2-CYCLOHEXEN-1-YL)AMINO).ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-D-GLUCOPYRANOSE
  • O-4,6-Dideoxy-4-(((1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-alpha-D-glucopyranosyl-(1-4)-O-alpha-D-glucopyranosyl-(1-4)-D-glucose
  • O-4,6-Dideoxy-4-(((1S-(1alpha,4alpha,5beta,6alpha))-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-alpha-D-glucopyranosyl-(1-4)-O-alpha-D-glucopyranosyl-(1-4)-D-glucose
  • T58MSI464G

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC96309558
  • UNII-T58MSI464G
  • DTXSID8046034
  • EINECS 260-030-7
  • SCHEMBL4606191

Physico-Chemical properties

IUPAC name(2R,3R,4R,5R)-4-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino]oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal
Molecular formulaC25H43NO18
Molecular weight645.605
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity137.92
LogP-8.3
Topological polar surface area329.0

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.