Isosorbide

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

What is the Isosorbide?

The molecule Isosorbide presents a molecular formula of C6H10O4 and its IUPAC name is (3S,3aR,6R,6aR)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol.

Isosorbide is a molecule with the chemical formula C6H14O3. It is a six-carbon molecule with a molecular weight of 118.17 g/mol. Isosorbide is insoluble in water and has a melting point of 46-48 °C. Isosorbide is a white, crystalline solid..

Isosorbide is used as a medication for the treatment of angina and heart failure. It is also used as a vasodilator. Isosorbide works by relaxing the blood vessels and increasing blood flow. This helps to reduce the symptoms of angina and heart failure. Isosorbide exists as a tablet, capsule, and solution. It can be found as an injection..

3D structure

Cartesian coordinates

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

2D drawing

 

Isosorbide KLDXJTOLSGUMSJ-JGWLITMVSA-N chemical compound 2D structure molecule svg
Isosorbide

 

Molecule descriptors

 
IUPAC name(3S,3aR,6R,6aR)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol
InChI codeInChI=1S/C6H10O4/c7-3-1-9-6-4(8)2-10-5(3)6/h3-8H,1-2H2/t3-,4+,5-,6-/m1/s1
InChI KeyKLDXJTOLSGUMSJ-JGWLITMVSA-N
SMILESO[C@H]1CO[C@@H]2[C@H](O)CO[C@H]12

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.

  • (+)-D-Isosorbide
  • (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diol
  • (3S,3aR,6R,6aR)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol
  • 1,4-Dianhydrosorbitol
  • 1,4:3,6-Dianhydro-D-glucitol
  • 1,4:3,6-Dianhydro-D-sorbitol
  • 1,4:3,6-Dianhydroglucitol
  • 1,4:3,6-Dianhydrosorbitol
  • 1,4; 3,6-dianhydrosorbitol
  • 1,6-Dianhydro-D-glucitol
  • 1,6-Dianhydro-D-sorbitol
  • 1,6-Dianhydrosorbitol
  • 1.4:3.6-dianhydro-D-glucitol
  • 1.4;3.6-dianhydro-D-glucitol
  • 652-67-5
  • A912284D-27E1-4FB0-91B8-86C8AB905297
  • AB01566931_01
  • AS-14140
  • AT-101
  • BBL029591
  • BIDD:GT0695
  • BRN 0080510
  • CCG-266173
  • CS-5157
  • D-1,4:3,6-Dianhydroglucitol
  • D-Glucitol, 1,4:3,6-dianhydro-
  • D-Glucitol,4:3,6-dianhydro-
  • D-Isosorbide
  • D-Sorbitol, {1,4:3,6-dianhydro(furo[3,2-b]furan-3,6-diol,} hexahydro-)
  • D-Sorbitol,4:3,6-dianhydro(furo[3,2-b]furan-3,6-diol, hexahydro-)
  • D00347
  • DB09401
  • DSSTox_CID_26196
  • DSSTox_GSID_46196
  • DSSTox_RID_81427
  • Devicoran
  • Dianhydro-D-glucitol
  • EC 211-492-3
  • Glucitol, 1,4:3,6-dianhydro-, D-
  • Glucitol,4:3,6-dianhydro-, D-
  • HSDB 3105
  • HY-B1469
  • Hydronol
  • I0407
  • Ismotic
  • Isobide
  • Isosorbida
  • Isosorbide
  • Isosorbide (JP17/USP/INN)
  • Isosorbidum
  • MFCD00064827
  • NCGC00160508-01
  • NCGC00160508-02
  • NCGC00160508-03
  • NSC 40725
  • NSC-40725
  • NSC40725
  • Polysorb P
  • Polysorb PS
  • Q1243800
  • SMP1_000177
  • STK801813
  • Sorbid
  • Sorbitol, 1,4:3,6-dianhydro-
  • Vascardin dinitrate
  • WXR179L51S
  • Z2785909604
  • isosorbide
  • s4204

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC18284778
  • CAS-652-67-5
  • UNII-WXR179L51S
  • AKOS005622709
  • DTXSID5046196
  • CHEMBL1200660
  • CHEBI:6060
  • Tox21_111861
  • Tox21_111861_1
  • EINECS 211-492-3
  • SCHEMBL15495

Physico-Chemical properties

IUPAC name(3S,3aR,6R,6aR)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol
Molecular formulaC6H10O4
Molecular weight146.141
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity31.22
LogP-1.5
Topological polar surface area58.9

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.