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 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 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
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 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
References
1. Brufani M, Cellai L, Cerrini S, Fedeli W, Marchi E, Segre A, Vaciago A. (1984)
X-ray crystal structure of 4-deoxy-3'-bromopyrido[1',2'-1,2]imidazo[5,4-c]rifamycin S.
J Antibiot (Tokyo), 37 (12): 1623-7. [PMID:6549316]
2. Gomi H, Jiang ZD, Adachi JA, Ashley D, Lowe B, Verenkar MP, Steffen R, DuPont HL. (2001)
In vitro antimicrobial susceptibility testing of bacterial enteropathogens causing traveler's diarrhea in four geographic regions.
Antimicrob Agents Chemother, 45 (1): 212-6. [PMID:11120968]
3. Hoover WW, Gerlach EH, Hoban DJ, Eliopoulos GM, Pfaller MA, Jones RN. (1993)
Antimicrobial activity and spectrum of rifaximin, a new topical rifamycin derivative.
Diagn Microbiol Infect Dis, 16 (2): 111-8. [PMID:8385592]