rifamycin SV   Click here for help

GtoPdb Ligand ID: 4570

Synonyms: Aemcolo®
Approved drug
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.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (2018))
IUPAC Name Click here for help
(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[^{4,7}.0^{5,28}]triaconta-1,3,5(28),9,19,21,25(29),26-octaen-13-yl acetate
International Nonproprietary Names Click here for help
INN number INN
2293 rifamycin
Synonyms Click here for help
Database Links Click here for help
CAS Registry No. 6998-60-3 (source: Scifinder)
ChEMBL Ligand CHEMBL437765
DrugCentral Ligand 4817
GtoPdb PubChem SID 178101291
PubChem CID 6324616
Search Google for chemical match using the InChIKey HJYYPODYNSCCOU-ODRIEIDWSA-N
Search Google for chemicals with the same backbone HJYYPODYNSCCOU
Search PubMed clinical trials rifamycin
Search PubMed titles rifamycin
Search PubMed titles/abstracts rifamycin
Search UniChem for chemical match using the InChIKey HJYYPODYNSCCOU-ODRIEIDWSA-N
Search UniChem for chemicals with the same backbone HJYYPODYNSCCOU