rifapentine   Click here for help

GtoPdb Ligand ID: 12014

Synonyms: DL 473 | MDL 473 | Priftin®
Approved drug PDB Ligand
rifapentine is an approved drug (FDA (1998))
Compound class: Synthetic organic
Comment: Rifapentine is a semisynthetic derivative of rifamycin and belongs to the ansamycin group of antibacterial compounds [1]. Rifapentine is on the World Health Organization's Model List of Essential Medicines (link provided in the Classification table, under the Summary tab below) for use as an oral antituberculosis medication.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 6
Rotatable bonds 6
Topological polar surface area 220.15
Molecular weight 876.45
XLogP 5.25
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(O)c(/C=N/N4CCN(CC4)C4CCCC4)c(c(c2c(c3C)O)O)NC(=O)/C(=C\C=C\[C@@H]([C@@H]([C@H]([C@H]([C@H]([C@@H]([C@@H]1C)OC(=O)C)C)O)C)O)C)/C
Isomeric SMILES C[C@H]1/C=C/C=C(\C(=O)Nc2c(c(c3c(c2O)c(c(c2c3C(=O)[C@](O2)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C)O)O)/C=N/N1CCN(CC1)C1CCCC1)/C
InChI InChI=1S/C47H64N4O12/c1-24-13-12-14-25(2)46(59)49-37-32(23-48-51-20-18-50(19-21-51)31-15-10-11-16-31)41(56)34-35(42(37)57)40(55)29(6)44-36(34)45(58)47(8,63-44)61-22-17-33(60-9)26(3)43(62-30(7)52)28(5)39(54)27(4)38(24)53/h12-14,17,22-24,26-28,31,33,38-39,43,53-57H,10-11,15-16,18-21H2,1-9H3,(H,49,59)/b13-12+,22-17+,25-14-,48-23+/t24-,26+,27+,28+,33-,38-,39+,43+,47-/m0/s1
InChI Key WDZCUPBHRAEYDL-GZAUEHORSA-N
References
1. Arioli V, Berti M, Carniti G, Randisi E, Rossi E, Scotti R. (1981)
Antibacterial activity of DL 473, a new semisynthetic rifamycin derivative.
J Antibiot (Tokyo), 34 (8): 1026-32. [PMID:7319918]