rifamycin SV   

GtoPdb Ligand ID: 4570

Synonyms: Aemcolo®
rifamycin SV is an approved drug (FDA (2018))
Comment: One of the Ansamycin group of antibiotics. Rifamycin is a natural antibiotic that is produced by Streptomyces mediterranei that exhibits antibiotic and antitubercular properties. Rifamycins are particularly effective against mycobacteria, and are most commonly used to treat tuberculosis, leprosy, and mycobacterium avium complex (MAC) infections.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 9
Hydrogen bond donors 6
Rotatable bonds 3
Topological polar surface area 201.31
Molecular weight 697.31
XLogP 3.97
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES COC1C=COC2(C)Oc3c(C2=O)c2c(O)cc(c(c2c(c3C)O)O)NC(=O)C(=CC=CC(C(C(C(C(C(C1C)OC(=O)C)C)O)C)O)C)C
Isomeric SMILES CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(O)cc(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
InChI InChI=1S/C37H47NO12/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41/h10-16,18-20,25,29-30,33,40-44H,1-9H3,(H,38,46)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1
InChI Key HJYYPODYNSCCOU-ODRIEIDWSA-N
Classification
Compound class Natural product or derivative
Approved drug? Yes (FDA (2018))
IUPAC Name
(7S,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1,3,5(28),9,19,21,25(29),26-octaen-13-yl acetate
International Nonproprietary Names
INN number INN
2293 rifamycin
Synonyms
Aemcolo®
Database Links
CAS Registry No. 6998-60-3 (source: Scifinder)
ChEBI CHEBI:29673
ChEMBL Ligand CHEMBL437765
DrugCentral Ligand 4817
GtoPdb PubChem SID 178101291
PubChem CID 6324616
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