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
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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
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
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
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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]