GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

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
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Fanos V, Mormile R, Benini D, Vecchini S, Cuzzolin L. (2000)
Flurithromycin-induced acute interstitial nephritis.
Pediatr Infect Dis J, 19 (4): 366-7. [PMID:10783037]
2. Hardy DJ, Hensey DM, Beyer JM, Vojtko C, McDonald EJ, Fernandes PB. (1988)
Comparative in vitro activities of new 14-, 15-, and 16-membered macrolides.
Antimicrob Agents Chemother, 32 (11): 1710-9. [PMID:3252753]
3. Saverino D, Debbia EA, Pesce A, Lepore AM, Schito GC. (1992)
Antibacterial profile of flurithromycin, a new macrolide.
J Antimicrob Chemother, 30 (3): 261-72. [PMID:1452490]
4. Toscano L, Fioriello G, Spagnoli R, Cappelletti L, Zanuso G. (1983)
New fluorinated erythromycins obtained by mutasynthesis.
J Antibiot (Tokyo), 36 (11): 1439-50. [PMID:6654754]