rokitamycin   Click here for help

GtoPdb Ligand ID: 12879

Synonyms: Ricamycin® | TMS-19-Q
Approved drug
rokitamycin is an approved drug
Compound class: Synthetic organic
Comment: Rokitamycin is a 16-membered semisynthetic macrolide antibacterial compound [3].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 16
Hydrogen bond donors 3
Rotatable bonds 15
Topological polar surface area 206.05
Molecular weight 828
XLogP 2.7
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES CCCC(=O)O[C@H]1[C@H](C)O[C@H](C[C@@]1(C)OC(=O)CC)O[C@@H]2[C@@H](C)O[C@H]([C@@H]([C@H]2N(C)C)O)O[C@H]3[C@@H](CC=O)C[C@@H](C)[C@H](/C=C/C=C/C[C@@H](C)OC(=O)C[C@H]([C@@H]3OC)O)O
Isomeric SMILES CCCC(=O)O[C@H]1[C@@H](O[C@H](C[C@@]1(C)OC(=O)CC)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2N(C)C)O)O[C@H]3[C@H](C[C@H]([C@H](/C=C/C=C/C[C@H](OC(=O)C[C@H]([C@@H]3OC)O)C)O)C)CC=O)C)C
InChI InChI=1S/C42H69NO15/c1-11-16-32(48)55-40-27(6)53-34(23-42(40,7)58-31(47)12-2)56-37-26(5)54-41(36(50)35(37)43(8)9)57-38-28(19-20-44)21-24(3)29(45)18-15-13-14-17-25(4)52-33(49)22-30(46)39(38)51-10/h13-15,18,20,24-30,34-41,45-46,50H,11-12,16-17,19,21-23H2,1-10H3/b14-13+,18-15+/t24-,25-,26-,27+,28+,29+,30-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1
InChI Key VYWWNRMSAPEJLS-MDWYKHENSA-N
References
1. Braga PC. (2002)
Rokitamycin: bacterial resistance to a 16-membered ring macrolide differs from that to 14- and 15-membered ring macrolides.
J Chemother, 14 (2): 115-31. [PMID:12017366]
2. Cinco M, Padovan D, Stinco G, Trevisan G. (1995)
In vitro activity of rokitamycin, a new macrolide, against Borrelia burgdorferi.
Antimicrob Agents Chemother, 39 (5): 1185-6. [PMID:7625812]
3. Sakakibara H, Okekawa O, Fujiwara T, Otani M, Omura S. (1981)
Acyl derivatives of 16-membered macrolides. I. Synthesis and biological properties of 3"-O-propionylleucomycin A5 (TMS-19-Q).
J Antibiot (Tokyo), 34 (8): 1001-10. [PMID:7319915]