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80214-83-1 molecular structure
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(10E)-6-{[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-[(5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy]-3,5,7,9,11,13-hexamethyl-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one

ChemBase ID: 132692
Molecular Formular: C41H76N2O15
Molecular Mass: 837.04654
Monoisotopic Mass: 836.52456974
SMILES and InChIs

SMILES:
CCC1C(C(C(/C(=N/OCOCCOC)/C(CC(C(C(C(C(C(=O)O1)C)OC1CC(C(C(O1)C)O)(C)OC)C)OC1C(C(CC(O1)C)N(C)C)O)(C)O)C)C)O)(C)O
Canonical SMILES:
COCCOCO/N=C/1\C(C)CC(C)(O)C(OC2OC(C)CC(C2O)N(C)C)C(C)C(OC2OC(C)C(C(C2)(C)OC)O)C(C(=O)OC(C(C(C1C)O)(C)O)CC)C
InChI:
InChI=1S/C41H76N2O15/c1-15-29-41(10,49)34(45)24(4)31(42-53-21-52-17-16-50-13)22(2)19-39(8,48)36(58-38-32(44)28(43(11)12)18-23(3)54-38)25(5)33(26(6)37(47)56-29)57-30-20-40(9,51-14)35(46)27(7)55-30/h22-30,32-36,38,44-46,48-49H,15-21H2,1-14H3/b42-31+
InChIKey:
RXZBMPWDPOLZGW-FEMONOMJSA-N

Cite this record

CBID:132692 http://www.chembase.cn/molecule-132692.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(10E)-6-{[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-[(5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy]-3,5,7,9,11,13-hexamethyl-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one
IUPAC Traditional name
roxithromycin
Synonyms
Erythromycin 9-(-O-[2-methoxyethoxy]methyloxime)
Roxithromycin
CAS Number
80214-83-1
MDL Number
MFCD00214389
PubChem SID
24899369
162226969
PubChem CID
5353933

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
R4393 external link Add to cart Please log in.
Data Source Data ID
PubChem 5353933 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.454023  H Acceptors 16 
H Donor LogD (pH = 5.5) -0.23886713 
LogD (pH = 7.4) 1.3162447  Log P 2.9999793 
Molar Refractivity 211.2376 cm3 Polarizability 85.90249 Å3
Polar Surface Area 216.89 Å2 Rotatable Bonds 13 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Safety Information Product Information Bioassay(PubChem)
RTECS
KF4990000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥90% (HPLC) expand Show data source
Suitability
suitable for 1694 per US EPA expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - R4393 external link
Biochem/physiol Actions
Semisynthetic erythromycin derivative. Impairs NADPH oxidase activation and alters translocation of its cytosolic components to the neutrophil membrane.
Roxithromycin impairs NADPH oxidase activation and alters translocation of its cytosolic components to the neutrophil membrane. It is similar in composition, chemical structure and mechanism of action to erythromycin, azithromycin, and clarithromycin. Roxithromycin binds to the subunit 50S of the bacterial ribosome, inhibiting the translocation of peptides1.
Application
Roxithromycin is a semi-synthetic macrolide antibiotic. Roxithromycin is used to block bacterial protein synthesis. Clinically, it is used to treat respiratory tract, urinary and soft tissue infections. It has a similar antimicrobial spectrum as erythromycin, but is the preferred treatment for certain gram-negative bacteria, such as Legionella pneumophila1.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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