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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]. It is an orally administered prodrug of the semi-synthetic erythromycin derivative erythromycyclamine.
2D Structure
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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.

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Physico-chemical Properties
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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.

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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

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
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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/)

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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

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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. US FDA (1995)
Withdrawn drug? Yes
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 Dirithromycin
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
Search Google for chemical match using the InChIKey WLOHNSSYAXHWNR-DWIOZXRMSA-N
Search Google for chemicals with the same backbone WLOHNSSYAXHWNR
Search PubMed clinical trials dirithromycin
Search PubMed titles dirithromycin
Search PubMed titles/abstracts dirithromycin
UniChem Compound Search for chemical match using the InChIKey WLOHNSSYAXHWNR-DWIOZXRMSA-N
UniChem Connectivity Search for chemical match using the InChIKey WLOHNSSYAXHWNR-DWIOZXRMSA-N