Details of the Drug

General Information of Drug (ID: DMKJ8LB)

Drug Name

Josamycin

Synonyms

Josacine; Josamicina; Josamycine; Josamycinum; EN 141; Kitasamycin A3; Leucomycin A3; Turimycin A5; Antibiotic yl-704 A3; Iosalide (TN); Josacine (TN); Josalid (TN); Josamicina [INN-Spanish]; Josamina (TN); Josamy (TN); Josamycin (TN); Josamycine [INN-French]; Josamycinum [INN-Latin]; Wilprafen (TN); Yl-704 A3; Josamycin [USAN:INN:JAN]; Josamycin (JP15/USAN/INN); Dro-2H-pyran-3-yl 3-methylbutanoate; Leucomycin V, 3-acetate 4B-(3-methylbutanoate); Leucomycin V, 3-acetate 4(sup B)-(3-methylbutanoate); Leucomycin V,3-acetate 4(sup beta)-(3-methylbutanoate)

Indication

Disease Entry	ICD 11	Status	REF
Bacterial infection	1A00-1C4Z	Approved	[1]

Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski): 3

Molecular Weight (mw)

828

Topological Polar Surface Area (xlogp)

2.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C42H69NO15
IUPAC Name: [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-acetyloxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] 3-methylbutanoate
Canonical SMILES: C[C@@H]1C/C=C/C=C/[C@@H]([C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)OC(=O)C)OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)OC(=O)CC(C)C)(C)O)N(C)C)O)CC=O)C)O
InChI: InChI=1S/C42H69NO15/c1-23(2)19-32(47)56-40-27(6)53-34(22-42(40,8)50)57-37-26(5)54-41(36(49)35(37)43(9)10)58-38-29(17-18-44)20-24(3)30(46)16-14-12-13-15-25(4)52-33(48)21-31(39(38)51-11)55-28(7)45/h12-14,16,18,23-27,29-31,34-41,46,49-50H,15,17,19-22H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27+,29+,30+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1
InChIKey: XJSFLOJWULLJQS-NGVXBBESSA-N

Cross-matching ID

PubChem CID: 5282165
ChEBI ID: CHEBI:31739
CAS Number: 16846-24-5
DrugBank ID: DB01321
TTD ID: D0X1WJ

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial 50S ribosomal RNA (Bact 50S rRNA)	TTUWYEA	NOUNIPROTAC	Binder	[2]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Drug information of Josamycin, 2008. eduDrugs.
2	The mechanism of action of macrolides, lincosamides and streptogramin B reveals the nascent peptide exit path in the ribosome. J Mol Biol. 2003 Jul 25;330(5):1005-14.
3	A synthetic alanyl-initiator tRNA with initiator tRNA properties as determined by fluorescence measurements: comparison to a synthetic alanyl-elongator tRNA. Nucleic Acids Res. 1991 Oct 25;19(20):5749-54.
4	An examination of the differential sensitivity to ketolide antibiotics in ermB strains of Streptococcus pyogenes and Streptococcus pneumoniae. Curr Microbiol. 2004 Oct;49(4):239-47.
5	Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria. Nature. 2001 Oct 25;413(6858):814-21.
6	Review of macrolides and ketolides: focus on respiratory tract infections. Drugs. 2001;61(4):443-98.
7	The ChEMBL database in 2017. Nucleic Acids Res. 2017 Jan 4;45(D1):D945-D954.
8	Depression of colony formation by human thymus-derived lymphocytes with rifampin and other antimicrobial agents. J Infect Dis. 1981 Jun;143(6):832-5.
9	Retapamulin inhibition of translation and 50S ribosomal subunit formation in Staphylococcus aureus cells. Antimicrob Agents Chemother. 2007 Sep;51(9):3385-7.
10	The streptogramin antibiotics: update on their mechanism of action. Expert Opin Investig Drugs. 1998 Apr;7(4):591-9.
11	2014 FDA drug approvals. Nat Rev Drug Discov. 2015 Feb;14(2):77-81.