Josamycin

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

What is the Josamycin?

The molecule Josamycin presents a molecular formula of C42H69NO15 and its IUPAC name is [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-acetyloxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] 3-methylbutanoate.

Josamycin is a macrolide antibiotic. It is used to treat infections caused by bacteria..

Josamycin is a white to yellowish-white powder. It is soluble in water and insoluble in organic solvents..

The chemical structure of josamycin is:.

Josamycin is produced by Streptomyces tsukubaensis..

It was first isolated in 1967 from a culture of Streptomyces tsukubaensis..

Josamycin is used to treat infections caused by bacteria including:.

respiratory tract infections.

urinary tract infections.

skin infections.

It is also used to prevent infections in people who are at risk of developing infections, such as:.

after surgery.

people with a weakened immune system.

Josamycin exists as capsules, tablets, and an oral suspension..

The usual adult dose is 500 mg twice daily. The usual dose for children is 10 mg/kg twice daily..

Josamycin should be taken with food..

Common side effects of josamycin include:.

nausea.

vomiting.

diarrhea.

stomach pain.

headache.

dizziness.

rash.

Josamycin can cause serious side effects including:.

liver problems.

kidney problems.

allergic reactions.

Josamycin should not be used by people who are allergic to it or any of its ingredients..

It should also not be used by people with liver or kidney disease..

Pregnant women should not take josamycin..

Josamycin can pass into breast milk and may harm a nursing baby. Women who are breastfeeding should not take josamycin..

3D structure

Cartesian coordinates

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

2D drawing

 

Josamycin XJSFLOJWULLJQS-NGVXBBESSA-N chemical compound 2D structure molecule svg
Josamycin

 

Molecule descriptors

 
IUPAC name[(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-acetyloxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] 3-methylbutanoate
InChI codeInChI=1S/C42H69NO15/c1-23(2)19-32(47)56-40-27(6)53-34(22-42(40,8)50)57-37-26(5)54-41(36(49)35(37)43(9)10)58-38-29(17-18-44)20-24(3)30(46)16-14-12-13-15-25(4)52-33(48)21-31(39(38)51-11)55-28(7)45/h12-14,16,18,23-27,29-31,34-41,46,49-50H,15,17,19-22H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27+,29+,30+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1
InChI KeyXJSFLOJWULLJQS-NGVXBBESSA-N
SMILESCO[C@@H]1[C@@H](O[C@@H]2O[C@H](C)[C@@H](O[C@H]3C[C@@](C)(O)[C@@H](OC(=O)CC(C)C)[C@H](C)O3)[C@H](N(C)C)[C@H]2O)[C@@H](CC=O)C[C@@H](C)[C@@H](O)/C=C/C=C/C[C@@H](C)OC(=O)C[C@H]1OC(C)=O

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,4R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-(acetyloxy)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy}-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl 3-methylbutanoate
  • 16846-24-5
  • 56689-45-3
  • 6-{6-[3-Acetyloxy-13-hydroxy-2-methoxy-7,14-dimethyl-6-oxa-5-oxo-16-(2-oxoethyl)cyclohexadeca-9,11-dienyloxy]-4-(dimethylamino)-5-hydroxy-2-methylperhydro-2H-pyran-3-yloxy}-4-hydroxy-2,4-dimethylperhydro-2H-pyran-3-yl 3-methylbutanoate
  • Antibiotic yl-704 A3
  • CCRIS 8511
  • CS-0013975
  • D01235
  • DB01321
  • EN 141
  • EN-141
  • EN-141;Kitasamycin A3;Leucomycin A3;Turimycin A5
  • HV13HFS217
  • HY-B1920
  • JM
  • Jomybel
  • Josacine
  • Josamicina
  • Josamycin
  • Josamycin (JP17/USAN/INN)
  • Josamycine
  • Josamycinum
  • Kitasamycin A3
  • LEUCOMYCIN V, 3-ACETATE 4(SUP .BETA.)-(3-METHYLBUTANOATE)
  • Leucomycin A3
  • Leucomycin V 3-acetate 4(beta)-(3-methylbutanoate)
  • Leucomycin V 3-acetate 4b-(3-methylbutanoate)
  • Leucomycin V, 3-acetate 4(sup B)-(3-methylbutanoate)
  • Leucomycin V, 3-acetate 4(sup beta)-(3-methylbutanoate)
  • Leucomycin V, 3-acetate 4B-(3-methylbutanoate)
  • MFCD00210320
  • NSC122223
  • Q423369
  • SR-01000883731
  • SR-01000883731-1
  • ST075007
  • Stereoisomer of 4-(acetyloxy)-6-((3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-4-O-(3-methyl-1-oxobutyl)-alpha-L-ribo-hexopyranosyl)-3-(dimethylamino)-beta-D-glucopyranosyl)oxy)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-diene-7-acetaldehyde
  • Stereoisomer of 7-(formylmethyl)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-6-yl 3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyl)-3-(dimethylamino)-beta-D-glucopyranoside 4'-acetate 4''-isovalerate
  • Stereoisomer of 7-(formylmethyl)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-6-yl 3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyl)-3-(dimethylamino)-beta-D-glucopyranoside 4'-acetate 4'-isovalerate
  • Turimycin A5
  • Yl-704 A3
  • [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-acetoxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyl-tetrahydropyran-3-yl]oxy-4-hydroxy-2,4-dimethyl-tetrahydropyran-3-yl] 3-methylbutanoate
  • [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-acetyloxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-
  • [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-acetyloxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] 3-methylbutanoate
  • hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] 3-methylbutanoate
  • iosalide
  • josamina
  • josamycin
  • leucomycin V 3-acetate 4(B)-(3-methylbutanoate)
  • leucomycin V 3-acetate 4beta-(3-methylbutanoate)
  • s4421

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC96006021
  • UNII-HV13HFS217
  • CHEMBL224436
  • CHEBI:31739
  • EINECS 240-871-6
  • SCHEMBL132829

Physico-Chemical properties

IUPAC name[(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-acetyloxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] 3-methylbutanoate
Molecular formulaC42H69NO15
Molecular weight827.995
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity212.62
LogP3.0
Topological polar surface area206.1

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.