rifamycin SV   Click here for help

GtoPdb Ligand ID: 4570

Synonyms: Aemcolo®
Approved drug
rifamycin SV is an approved drug (FDA (2018))
Compound class: Natural product
Comment: One of the Ansamycin group of antibacterials. Rifamycin is a natural antibacterial that is produced by Streptomyces mediterranei that exhibits antibacterial and antitubercular properties. Rifamycins are particularly effective against mycobacteria, and are most commonly used to treat tuberculosis, leprosy, and mycobacterium avium complex (MAC) infections.
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2D Structure
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Physico-chemical Properties
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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
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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 Click here for help
Compound class Natural product
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[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 Click here for help
INN number INN
2293 rifamycin
Synonyms Click here for help
Aemcolo®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Rifamycin
Other databases
CAS Registry No. 6998-60-3 (source: Scifinder)
ChEBI CHEBI:29673
ChEMBL Ligand CHEMBL437765
DrugCentral Ligand 4817
GtoPdb PubChem SID 178101291
LIPID MAPS LMPK05000005
PubChem CID 6324616
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UniChem Compound Search for chemical match using the InChIKey HJYYPODYNSCCOU-ODRIEIDWSA-N
UniChem Connectivity Search for chemical match using the InChIKey HJYYPODYNSCCOU-ODRIEIDWSA-N