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.
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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.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: rifampicin

2D Structure
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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.

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Physico-chemical Properties
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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.

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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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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.

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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
Bioactivity Comments
Rifampicin inhibits uptake of estrone-3-sulfate by bovine Oatp1a2 in vitro (by approximately 40%), by competing with estrone-3-sulfate for the high affinity substrate binding site [4].
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
OATP1B1
OATP1B3
Selectivity at nuclear hormone receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Pregnane X receptor Hs Agonist Agonist 5.5 – 6.0 pEC50 - 1,3
⤷ pEC50 5.5 – 6.0 [1,3]
Selectivity at transporters
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
OATP1B1 Hs Inhibitor Inhibition 6.0 pKi - 2
⤷ pKi 6.0 (Ki 1.1x10-6 M) [2]
Description: Inhibition of atorvastatin transport by OATP1B1.
OATP1A2 Hs Inhibitor Inhibition 4.3 pKi - 6
⤷ pKi 4.3 (Ki 5.1x10-5 M) [6]
OATP1B3 Hs Inhibitor Inhibition 5.8 pIC50 - 2,5
⤷ pIC50 5.8 (IC50 1.6x10-6 M) [2,5]