rifampicin   Click here for help

GtoPdb Ligand ID: 2765

Synonyms: Rifadin® | rifampin
Approved drug PDB Ligand
rifampicin is an approved drug (FDA (1971))
Compound class: Natural product or derivative
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.
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: rifampicin

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
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
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
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 Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
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 Rifampicin, Rifampin
Reactome Drug Reactome logo R-ALL-9695545, R-ALL-9639432
Reactome Reaction Reactome logo R-HSA-9685655, R-HSA-9697086
Other databases
CAS Registry No. 13292-46-1
ChEBI CHEBI:28077
ChEMBL Ligand CHEMBL374478
DrugBank Ligand DB01045
GtoPdb PubChem SID 135652711
PubChem CID 135900090
RCSB PDB Ligand RFP
Search Google for chemical match using the InChIKey JQXXHWHPUNPDRT-WLSIYKJHSA-N
Search Google for chemicals with the same backbone JQXXHWHPUNPDRT
Search PubMed clinical trials rifampicin
Search PubMed titles rifampicin
Search PubMed titles/abstracts rifampicin
UniChem Compound Search for chemical match using the InChIKey JQXXHWHPUNPDRT-WLSIYKJHSA-N
UniChem Connectivity Search for chemical match using the InChIKey JQXXHWHPUNPDRT-WLSIYKJHSA-N
Wikipedia Rifampicin