rifampicin   Click here for help

GtoPdb Ligand ID: 2765

Synonyms: Rifadin® | rifampin
Approved drug PDB Ligand
rifampicin is an approved drug (FDA (1971))
Comment: As with many natural products with complex structures, there is some ambiguity as to the exact structure of rifampicin. Common representations of the structure include CID 5458213, and CID 5381226.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 6
Rotatable bonds 5
Topological polar surface area 220.15
Molecular weight 822.41
XLogP 4
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES COC1C=COC2(C)Oc3c(C2=O)c2c(O)c(C=NN4CCN(CC4)C)c(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)c(/C=N/N4CCN(CC4)C)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
InChI InChI=1S/C43H58N4O12/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49/h11-14,19-21,23-25,29,34-35,39,49-53H,15-18H2,1-10H3,(H,45,55)/b12-11+,19-14+,22-13-,44-20+/t21-,23+,24+,25+,29-,34-,35+,39+,43-/m0/s1
InChI Key JQXXHWHPUNPDRT-WLSIYKJHSA-N
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (1971))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
International Nonproprietary Names Click here for help
INN number INN
2323 rifampicin
Synonyms Click here for help
Rifadin® | rifampin
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 1450
Other databases
CAS Registry No. 13292-46-1
ChEBI CHEBI:28077
ChEMBL Ligand CHEMBL374478
DrugBank Ligand DB01045
GtoPdb PubChem SID 135652711
PubChem CID 25141428
RCSB PDB Ligand RFP
Search Google for chemical match using the InChIKey JQXXHWHPUNPDRT-WLSIYKJHSA-N
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Search PubMed clinical trials rifampicin
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Search UniChem for chemical match using the InChIKey JQXXHWHPUNPDRT-WLSIYKJHSA-N
Search UniChem for chemicals with the same backbone JQXXHWHPUNPDRT
Wikipedia Rifampicin