L-708365   Click here for help

GtoPdb Ligand ID: 10980

Synonyms: L 708,365 | L 708365 | L-708,365
Compound class: Synthetic organic
Comment: L-708365 is an azalide derivative of erythromycin [1]. It has improved acid stability compared to erythromycin, azithromycin and clarithromycin.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 14
Hydrogen bond donors 5
Rotatable bonds 9
Topological polar surface area 180.08
Molecular weight 774.52
XLogP 2.5
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES C=CCN1C[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](CC)OC(=O)[C@@H]([C@H]([C@@H]([C@H]([C@](C[C@H]1C)(C)O)O[C@@H]1O[C@H](C)C[C@@H]([C@H]1O)N(C)C)C)O[C@@H]1O[C@@H](C)[C@@H]([C@](C1)(C)OC)O)C
Isomeric SMILES C=CCN1C[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](CC)OC(=O)[C@@H]([C@H]([C@@H]([C@H]([C@](C[C@H]1C)(C)O)O[C@@H]1O[C@H](C)C[C@@H]([C@H]1O)N(C)C)C)O[C@@H]1O[C@@H](C)[C@@H]([C@](C1)(C)OC)O)C
InChI InChI=1S/C40H74N2O12/c1-15-17-42-21-22(3)33(44)40(11,48)29(16-2)52-36(46)26(7)32(53-30-20-39(10,49-14)34(45)27(8)51-30)25(6)35(38(9,47)19-23(42)4)54-37-31(43)28(41(12)13)18-24(5)50-37/h15,22-35,37,43-45,47-48H,1,16-21H2,2-14H3/t22-,23+,24+,25-,26+,27-,28-,29+,30-,31+,32-,33+,34-,35+,37-,38+,39+,40+/m0/s1
InChI Key ZZRQNCPNJLVUMK-UZSBJOJWSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(2R,3S,4R,5S,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-7-prop-2-enyl-1-oxa-7-azacyclopentadecan-15-one
Synonyms Click here for help
L 708,365 | L 708365 | L-708,365
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 271
Other databases
GtoPdb PubChem SID 405560421
PubChem CID 10462917
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