dirithromycin   Click here for help

GtoPdb Ligand ID: 12928

Synonyms: AS-E 136 | Dynabac® | LY237216
Approved drug PDB Ligand
dirithromycin is an approved drug (FDA (1995))
Compound class: Synthetic organic
Comment: Dirithromycin is a 14-membered macrolide antibacterial compound [1].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 16
Hydrogen bond donors 5
Rotatable bonds 12
Topological polar surface area 196.33
Molecular weight 835.08
XLogP 1.56
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES CC[C@@H]1[C@](C)([C@H]2[C@@H](C)[C@H]([C@H](C)C[C@](C)([C@@H]([C@@H](C)[C@@H]([C@@H](C)C(=O)O1)O[C@H]3C[C@](C)([C@H]([C@H](C)O3)O)OC)O[C@H]4[C@@H]([C@H](C[C@@H](C)O4)N(C)C)O)O)N[C@@H](COCCOC)O2)O
Isomeric SMILES CC[C@@H]1[C@@]([C@H]2[C@H]([C@H]([C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)OC)C)O[C@H]4[C@@H]([C@H](C[C@H](O4)C)N(C)C)O)(C)O)C)N[C@H](O2)COCCOC)C)(C)O
InChI InChI=1S/C42H78N2O14/c1-15-29-42(10,49)37-24(4)32(43-30(56-37)21-52-17-16-50-13)22(2)19-40(8,48)36(58-39-33(45)28(44(11)12)18-23(3)53-39)25(5)34(26(6)38(47)55-29)57-31-20-41(9,51-14)35(46)27(7)54-31/h22-37,39,43,45-46,48-49H,15-21H2,1-14H3/t22-,23-,24+,25+,26-,27+,28+,29-,30-,31+,32+,33-,34+,35+,36-,37-,39+,40-,41-,42-/m1/s1
InChI Key WLOHNSSYAXHWNR-DWIOZXRMSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1995))
IUPAC Name Click here for help
(1S,2R,4R,5R,6S,7S,8R,11R,12R,13R,15R,17S)-5-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyloxan-2-yl]oxy-11-ethyl-4,12-dihydroxy-7-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-15-(2-methoxyethoxymethyl)-2,4,6,8,12,17-hexamethyl-10,14-dioxa-16-azabicyclo[11.3.1]heptadecan-9-one
International Nonproprietary Names Click here for help
INN number INN
5694 dirithromycin
Synonyms Click here for help
AS-E 136 | Dynabac® | LY237216
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo
Other databases
BindingDB Ligand 59397
CAS Registry No. 62013-04-1 (source: Scifinder)
ChEBI CHEBI:474014
ChEMBL Ligand CHEMBL1237072
DrugBank Ligand DB00954
DrugCentral Ligand 925
GtoPdb PubChem SID 485206049
PubChem CID 6473883
RCSB PDB Ligand DI0
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UniChem Compound Search for chemical match using the InChIKey WLOHNSSYAXHWNR-DWIOZXRMSA-N
UniChem Connectivity Search for chemical match using the InChIKey WLOHNSSYAXHWNR-DWIOZXRMSA-N