rifaximin   Click here for help

GtoPdb Ligand ID: 12012

Synonyms: L/105 | Rifamycin L 105 | Xifaxan®
Approved drug PDB Ligand
rifaximin is an approved drug (FDA (2004))
Compound class: Synthetic organic
Comment: Rifaximin is a semisynthetic derivative of rifamycin and belongs to the ansamycin group of antibacterial compounds [1]. It has broad spectrum activity against Gram-positive and Gram-negative bacteria.
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 10
Hydrogen bond donors 5
Rotatable bonds 3
Topological polar surface area 198.38
Molecular weight 785.35
XLogP 6.08
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(c(c3C)O)c(O)c(c3c2nc2n3ccc(c2)C)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
Isomeric SMILES C[C@H]1/C=C/C=C(\C(=O)Nc2c(c3c(c4c(c(c3O)C)O[C@@](C4=O)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)c1c2n2ccc(cc2n1)C)O)/C
InChI InChI=1S/C43H51N3O11/c1-19-14-16-46-28(18-19)44-32-29-30-37(50)25(7)40-31(29)41(52)43(9,57-40)55-17-15-27(54-10)22(4)39(56-26(8)47)24(6)36(49)23(5)35(48)20(2)12-11-13-21(3)42(53)45-33(34(32)46)38(30)51/h11-18,20,22-24,27,35-36,39,48-51H,1-10H3,(H,45,53)/b12-11+,17-15+,21-13-/t20-,22+,23+,24+,27-,35-,36+,39+,43-/m0/s1
InChI Key NZCRJKRKKOLAOJ-XRCRFVBUSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2004))
IUPAC Name Click here for help
[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,36-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22,30-octamethyl-6,23-dioxo-8,37-dioxa-24,27,33-triazahexacyclo[23.10.1.14,7.05,35.026,34.027,32]heptatriaconta-1(35),2,4,9,19,21,25(36),26(34),28,30,32-undecaen-13-yl] acetate
International Nonproprietary Names Click here for help
INN number INN
5244 rifaximin
Synonyms Click here for help
L/105 | Rifamycin L 105 | Xifaxan®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Rifaximin
Other databases
CAS Registry No. 80621-81-4 (source: Scifinder)
ChEBI CHEBI:75246
ChEMBL Ligand CHEMBL1617
DrugBank Ligand DB01220
GtoPdb PubChem SID 464244153
PubChem CID 6436173
RCSB PDB Ligand RXM
Search Google for chemical match using the InChIKey NZCRJKRKKOLAOJ-XRCRFVBUSA-N
Search Google for chemicals with the same backbone NZCRJKRKKOLAOJ
Search PubMed clinical trials rifaximin
Search PubMed titles rifaximin
Search PubMed titles/abstracts rifaximin
UniChem Compound Search for chemical match using the InChIKey NZCRJKRKKOLAOJ-XRCRFVBUSA-N
UniChem Connectivity Search for chemical match using the InChIKey NZCRJKRKKOLAOJ-XRCRFVBUSA-N
Wikipedia Rifaximin