ChemSpider 2D Image | Dirithromycin | C42H78N2O14

Dirithromycin

  • Molecular FormulaC42H78N2O14
  • Average mass835.074 Da
  • Monoisotopic mass834.545288 Da
  • ChemSpider ID4976073

  • defined stereocentres - 20 of 20 defined stereocentres

More details:

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(1R,2R,3R,6R,7S,8S,9R,10R,12R,13S,15R,17S)-3-Ethyl-2,10-dihydroxy-15-[(2-methoxyethoxy)methyl]-2,6,8,10,12,17-hexamethyl-5-oxo-9-{[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy}-4,16- dioxa-14-azabicyclo[11.3.1]heptadec-7-yl 2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranoside [ACD/IUPAC Name]
(1R,2R,3R,6R,7S,8S,9R,10R,12R,13S,15R,17S)-3-Ethyl-2,10-dihydroxy-15-[(2-methoxyethoxy)methyl]-2,6,8,10,12,17-hexamethyl-5-oxo-9-{[3,4,6-tridesoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy}-4,16 -dioxa-14-azabicyclo[11.3.1]heptadec-7-yl-2,6-didesoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosid [German] [ACD/IUPAC Name]
1801D76STL
2,6-Didésoxy-3-C-méthyl-3-O-méthyl-α-L-ribo-hexopyranoside de (1R,2R,3R,6R,7S,8S,9R,10R,12R,13S,15R,17S)-3-éthyl-2,10-dihydroxy-15-[(2-méthoxyéthoxy)méthyl]-2,6,8,10,12,17-hexaméthyl-5-oxo-9-{[3,4 ,6-tridésoxy-3-(diméthylamino)-β-D-xylo-hexopyranosyl]oxy}-4,16-dioxa-14-azabicyclo[11.3.1]heptadéc-7-yle [French] [ACD/IUPAC Name]
4,16-Dioxa-14-azabicyclo[11.3.1]heptadecan-5-one, 7-[(2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy]-3-ethyl-2,10-dihydroxy-15-[(2-methoxyethoxy)methyl]-2,6,8,10,12,17-hexamethyl-9- [[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-, (1R,2R,3R,6R,7S,8S,9R,10R,12R,13S,15R,17S)- [ACD/Index Name]
Dirithromycin [INN] [USP] [Wiki]
dirithromycine [French] [INN]
dirithromycine
dirithromycinum [Latin] [INN]
diritromicina [Spanish] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

5694 [DBID]
4225019 [DBID]
AIDS007805 [DBID]
AIDS-007805 [DBID]
ASE-136 [DBID]
DivK1c_006964 [DBID]
KBio1_001908 [DBID]
KBio2_001956 [DBID]
KBio2_004524 [DBID]
KBio2_007092 [DBID]
More...
  • Miscellaneous

    • Chemical Class:

      The hemi-aminal resulting from the condensation of the erythromycin derivative (9<stereo>S</stereo>)-erythromycyclamine with 2-(2-methoxyethoxy)acetaldehyde. As the oxazine ring containing the hemi-am inal group is unstable under both acidic and alkaline conditions, dirithromycin functions as a more lipid-soluble prodrug for (9<stereo>S</stereo>)-erythromycyclamine. Administered as enteric coated t ablets to protect it from acid catalysed hydrolysis in the stomach, it is used to treat respiratory tract, skin, and soft tissue infections caused by susceptible organisms. ChEBI CHEBI:474014
      The hemi-aminal resulting from the condensation of the erythromycin derivative (9S)-erythromycyclamine with 2-(2-methoxyethoxy)acetaldehyde. As the oxazine ring containing the hemi-am; inal group is u nstable under both acidic and alkaline conditions, dirithromycin functions as a more lipid-soluble prodrug for (9S)-erythromycyclamine. Administered as enteric coated t; ablets to protect it from acid catalysed hydrolysis in the stomach, it is used to treat respiratory tract, skin, and soft tissue infections caused by susceptible organisms. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:474014
      The hemi-aminal resulting from the condensation of the erythromycin derivative (9S)-erythromycyclamine with 2-(2-methoxyethoxy)acetaldehyde. As the oxazine ring containing the hemi-aminal group is uns table under both acidic and alkaline conditions, dirithromycin functions as a more lipid-soluble prodrug for (9S)-erythromycyclamine. Administered as enteric coated tablets to protect it from acid cat alysed hydrolysis in the stomach, it is used to treat respiratory tract, skin, and soft tissue infections caused by susceptible organisms. ChEBI CHEBI:474014

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.2±0.1 g/cm3
Boiling Point: 871.8±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.6 mmHg at 25°C
Enthalpy of Vaporization: 144.0±6.0 kJ/mol
Flash Point: 481.0±34.3 °C
Index of Refraction: 1.533
Molar Refractivity: 217.5±0.4 cm3
#H bond acceptors: 16
#H bond donors: 5
#Freely Rotating Bonds: 12
#Rule of 5 Violations: 3
ACD/LogP: 2.84
ACD/LogD (pH 5.5): -0.84
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): 1.93
ACD/BCF (pH 7.4): 10.83
ACD/KOC (pH 7.4): 109.79
Polar Surface Area: 196 Å2
Polarizability: 86.2±0.5 10-24cm3
Surface Tension: 49.7±5.0 dyne/cm
Molar Volume: 700.6±5.0 cm3

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