Indomethacin acyl-B-D-glucuronide

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

What is the Indomethacin acyl-B-D-glucuronide?

The molecule Indomethacin acyl-B-D-glucuronide presents a molecular formula of C25H24ClNO10 and its IUPAC name is (2S,3S,4S,5R,6S)-6-[2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid.

Indomethacin acyl-B-D-glucuronide (IAMG) is a molecule that is formed when the drug indomethacin is metabolized by the body. IAMG is then excreted in the urine..

Indomethacin is a nonsteroidal anti-inflammatory drug (NSAID) that is used to treat various conditions such as arthritis, gout, and menstrual cramps. It works by inhibiting the production of prostaglandins, which are substances that play a role in pain and inflammation..

IAMG is the major metabolite of indomethacin in humans and is thought to contribute to the therapeutic effects of the drug. IAMG is also thought to be responsible for some of the side effects of indomethacin, such as gastrointestinal bleeding and ulcers..

Indomethacin and IAMG are both absorbed from the gastrointestinal tract and are distributed to all tissues of the body. IAMG is then excreted in the urine..

The half-life of IAMG is about 3 hours. This means that it takes about 3 hours for the body to eliminate half of the IAMG that is in the system..

IAMG is a metabolite of indomethacin and is thought to contribute to the therapeutic effects of the drug. IAMG is also thought to be responsible for some of the side effects of indomethacin..

3D structure

Cartesian coordinates

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

2D drawing

 

Indomethacin acyl-B-D-glucuronide QCBWEVBGELGABM-CZLVRFMKSA-N chemical compound 2D structure molecule svg
Indomethacin acyl-B-D-glucuronide

 

Molecule descriptors

 
IUPAC name(2S,3S,4S,5R,6S)-6-[2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI codeInChI=1S/C25H24ClNO10/c1-11-15(10-18(28)36-25-21(31)19(29)20(30)22(37-25)24(33)34)16-9-14(35-2)7-8-17(16)27(11)23(32)12-3-5-13(26)6-4-12/h3-9,19-22,25,29-31H,10H2,1-2H3,(H,33,34)/t19-,20-,21+,22-,25+/m0/s1
InChI KeyQCBWEVBGELGABM-CZLVRFMKSA-N
SMILESCOc1ccc2c(c1)c(CC(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O)c(C)n2C(=O)c1ccc(Cl)cc1

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.

  • (2S,3S,4S,5R,6S)-6-(2-(1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-indol-3-yl)acetyl)oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
  • (2S,3S,4S,5R,6S)-6-[2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
  • .BETA.-D-GLUCOPYRANURONIC ACID, 1-(1-(4-CHLOROBENZOYL)-5-METHOXY-2-METHYL-1H-INDOLE-3-ACETATE)
  • 75523-11-4
  • A-D-glucuronide
  • B7MV2JQJ3W
  • INDOMETHACIN ACYL-B-D-GLUCURONIDE
  • INDOMETHACIN GLUCURONIDE
  • Indomethacin Acyl-
  • Indomethacin Acyl-?-D-glucuronide
  • Indomethacin Acyl-beta-D-glucuronide
  • Indomethacin acyl glucuronide
  • Indomethacin acyl-B-D-glucuronide
  • W-203729
  • beta-D-Glucopyranuronic acid, 1-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate)

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC84386263
  • UNII-B7MV2JQJ3W
  • CHEMBL2074828
  • CHEBI:184406

Physico-Chemical properties

IUPAC name(2S,3S,4S,5R,6S)-6-[2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
Molecular formulaC25H24ClNO10
Molecular weight533.912
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity128.71
LogP1.3
Topological polar surface area164.8

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.