rifaquizinone   Click here for help

GtoPdb Ligand ID: 11028

Synonyms: CBR-2092 | TNP-2092
Compound class: Synthetic organic
Comment: Rifaquizinone (formerly CBR-2092, then TNP-2092) is a rifamycin-quinolone hybrid antibacterial compound [2]. It exerts combined effects on bacterial RNA polymerase, DNA gyrase and DNA topoisomerase IV, although RNA polymerase has been reporetd as the primary cellular target [4]. Rifaquizinone was developed for potential to treat biofilm associated infections such as those caused by staphylococci [3-4]. Initial development was by Cumbre Pharmaceuticals, but it is now being taken forward by TenNor Therapeutics, hence the change in research code.
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 15
Hydrogen bond donors 7
Rotatable bonds 11
Topological polar surface area 282.17
Molecular weight 1204.57
XLogP 9.24
No. Lipinski's rules broken 4

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(O)c(/C=N/N4CCC(CC4)N(C4(CC4)[C@@H]4CCN(C4)c4c(F)cn5c(c4C)c(cc(c5=O)C(=O)O)C4CC4)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
Isomeric SMILES CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(O)c(/C=N/N4CCC(CC4)N(C4(CC4)[C@@H]4CCN(C4)c4c(F)cn5c(c4C)c(cc(c5=O)C(=O)O)C4CC4)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/C65H81FN6O15/c1-31-13-12-14-32(2)61(80)68-50-44(56(77)47-48(57(50)78)55(76)37(7)59-49(47)60(79)64(9,87-59)85-26-20-46(84-11)33(3)58(86-38(8)73)36(6)54(75)35(5)53(31)74)28-67-71-24-18-41(19-25-71)69(10)65(21-22-65)40-17-23-70(29-40)52-34(4)51-42(39-15-16-39)27-43(63(82)83)62(81)72(51)30-45(52)66/h12-14,20,26-28,30-31,33,35-36,39-41,46,53-54,58,74-78H,15-19,21-25,29H2,1-11H3,(H,68,80)(H,82,83)/b13-12+,26-20+,32-14-,67-28+/t31-,33+,35+,36+,40+,46-,53-,54+,58+,64-/m0/s1
InChI Key OPZFMLLAJBIKAN-KYGXCNJYSA-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/)

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