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Compound InformationSONAR Target prediction
Name:

DIRITHROMYCIN

Unique Identifier:SPE01504144
MolClass: Checkout models in ver1.5 and ver1.0
Molecular Formula:
Molecular Weight:756.454 g/mol
X log p:-2.064  (online calculus)
Lipinksi Failures2
TPSA103.38
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptors Count:16
Rotatable Bond Count:12
Canonical Smiles:CCC1OC(=O)C(C)C(OC2CC(C)(OC)C(O)C(C)O2)C(C)C(OC2OC(C)CC(C2O)N(C)C)C(C)
(O)CC(C)C2NC(COCCOC)OC(C2C)C1(C)O
Source:semisynthetic
Reference:Drugs 61: 443 (2001)
Therapeutics:antibacterial
Generic_name:Dirithromycin
Chemical_iupac_name:9-(4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl)oxy-3-ethyl-2,10-dihydroxy-7-(5-hydr
oxy-4-methoxy-4,6-dimethyl-oxan-2-yl)oxy-15-(2-methoxyethoxymethyl)-2,6,8,10,12,17-h
examethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one
Drug_type:Approved Drug
Pharmgkb_id:PA449368
Drugbank_id:APRD00931
H2o_solubility:Poor
Logp:2.833
Cas_registry_number:62013-04-1
Drug_category:Anti-infectives; Macrolides; ATC:J01FA13
Indication:For the treatment of the following mild-to-moderate infections caused by susceptible
strains of microorganisms: acute bacterial exacerbations of chronic bronchitis,
secondary bacterial infection of acute bronchitis, community-acquired pneumonia,
pharyngitis/tonsilitis, and uncomplicated skin and skin structure infections.
Pharmacology:Dirithromycin is a pro-drug which is converted non-enzymatically during intestinal
absorption into the microbiologically active moiety erythromycylamine.
Erythromycylamine exerts its activity by binding to the 50S ribosomal subunits of
susceptible mircoorganisms resulting in inhibition of protein synthesis.
Dirithromycin/erythromycylamine has been shown to be active against most strains of
the following microorganisms both in vitro and in clinical infections:
Staphylococcus aureus (methicillin-susceptible strains only),
Streptococcus pneumoniae, Streptococcus pyogenes, Haemophilus
influenzae
, Legionella pneumophila, Moraxella catarrhalis, and
Mycoplasma pneumoniae.
Mechanism_of_action:Dirithromycin prevents bacteria from growing, by interfering with their protein
synthesis. Dirithromycin binds to the 50S subunit of the 70S bacterial ribosome, and
thus inhibits the translocation of peptides. Dirithromycin has over 10 times higher
affinity to the subunit 50S than erythromycin. In addition, dirithromycin binds
simultaneously in to two domains of 23S RNA of the ribosomal subunit 50S, where
older macrolides bind only in one. Dirithromycin can also inhibit the formation of
ribosomal subunits 50S and 30S.
Organisms_affected:Enteric bacteria and other eubacteria

Found: 205 nonactive as graph: single | with analogs [1] << Back 201 202 203 204 205
Species: 4932
Condition: YPT6
Replicates: 2
Raw OD Value: r im 0.5238±0.0374767
Normalized OD Score: sc h 0.9970±0.0465483
Z-Score: 0.1233±0.487884
p-Value: 0.73207
Z-Factor: -22.5608
Fitness Defect: 0.3119
Bioactivity Statement: Nonactive
Experimental Conditions
Library:SPECMTS3
Plate Number and Position:20|F5
Drug Concentration:50.00 nM
OD Absorbance:600 nm
Robot Temperature:25.70 Celcius
Date:2008-06-05 YYYY-MM-DD
Plate CH Control (+):0.041124999999999995±0.00110
Plate DMSO Control (-):0.5084750000000001±0.01236
Plate Z-Factor:0.9015
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DBLink | Rows returned: 7<< Back 1 2
6917067 (1S,2R,3R,6R,7S,8S,9R,10R,12R,13S,15R,17S)-9-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl
]oxy-3-ethyl-2,10-dihydroxy-7-[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl]oxy-15-(2-methox
yethoxymethyl)-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one

internal high similarity DBLink | Rows returned: 0

active | Cluster 14145 | Additional Members: 11 | Rows returned: 1
SPE01501176 0.195652173913043

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