flurithromycin   Click here for help

GtoPdb Ligand ID: 12927

Synonyms: (8S)-8-fluoroerythromycin A | P-0501A
Approved drug
flurithromycin is an approved drug
Compound class: Synthetic organic
Comment: Flurithromycin is a 14-membered macrolide antibacterial compound, originally isolated from Streptomyces erythraeus using a mutational biosynthesis approach [4]. It is a fluorinated derivative of erythromycin with improved acid stability.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 14
Hydrogen bond donors 5
Rotatable bonds 7
Topological polar surface area 193.91
Molecular weight 751.92
XLogP 1.19
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CC[C@@H]1[C@](C)([C@@H]([C@@H](C)C(=O)[C@](C)(C[C@](C)([C@@H]([C@@H](C)[C@@H]([C@@H](C)C(=O)O1)O[C@H]2C[C@](C)([C@H]([C@H](C)O2)O)OC)O[C@H]3[C@@H]([C@H](C[C@@H](C)O3)N(C)C)O)O)F)O)O
Isomeric SMILES CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)(C)F)C)O)(C)O
InChI InChI=1S/C37H66FNO13/c1-14-24-37(10,46)29(42)21(5)28(41)34(7,38)17-35(8,45)31(52-33-26(40)23(39(11)12)15-18(2)48-33)19(3)27(20(4)32(44)50-24)51-25-16-36(9,47-13)30(43)22(6)49-25/h18-27,29-31,33,40,42-43,45-46H,14-17H2,1-13H3/t18-,19+,20-,21+,22+,23+,24-,25+,26-,27+,29-,30+,31-,33+,34+,35-,36-,37-/m1/s1
InChI Key XOEUHCONYHZURQ-HNUBZJOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes
IUPAC Name Click here for help
(3R,4S,5S,6R,7R,9S,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-9-fluoro-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
International Nonproprietary Names Click here for help
INN number INN
5534 flurithromycin
Synonyms Click here for help
(8S)-8-fluoroerythromycin A | P-0501A
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo
Other databases
CAS Registry No. 82664-20-8 (source: Scifinder)
ChEBI CHEBI:131719
ChEMBL Ligand CHEMBL2106403
DrugBank Ligand DB13338
DrugCentral Ligand 1221
GtoPdb PubChem SID 485206048
PubChem CID 71260
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UniChem Compound Search for chemical match using the InChIKey XOEUHCONYHZURQ-HNUBZJOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey XOEUHCONYHZURQ-HNUBZJOYSA-N