Ro-406890   Click here for help

GtoPdb Ligand ID: 11048

Synonyms: ceftrazonal | Ro 40-6890 | Ro 406890 | Ro406890
Compound class: Synthetic organic
Comment: Ro-406890 is a broad spectrum cephalosporin antibacterial [4]. We show the structure for the parent molecule. Biological data may have been generated using the sodium salt. It has also been synthesised as the orally absorbable ester Ro 41-3399 (a.k.a. ceftrazonal bopentil) [1].
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 3
Rotatable bonds 8
Topological polar surface area 213.11
Molecular weight 438.05
XLogP -2.96
No. Lipinski's rules broken 0
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/N=C(\c1csc(n1)N)/C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CN=[N+]=[N-]
Isomeric SMILES CO/N=C(\c1csc(n1)N)/C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CN=[N+]=[N-]
InChI InChI=1S/C14H14N8O5S2/c1-27-20-7(6-4-29-14(15)18-6)10(23)19-8-11(24)22-9(13(25)26)5(2-17-21-16)3-28-12(8)22/h4,8,12H,2-3H2,1H3,(H2,15,18)(H,19,23)(H,25,26)/b20-7+/t8-,12-/m1/s1
InChI Key RIBNLVJVYUATJJ-XPPPSQRSSA-N
References
1. Angehrn P, Hohl P, Hubschwerlen C, Page M, Then R. (1992)
Antibacterial properties of Ro 40-6890, a broad-spectrum cephalosporin, and its novel orally absorbable ester, Ro 41-3399.
Antimicrob Agents Chemother, 36 (12): 2825-34. [PMID:1482153]
2. Hohl P, Zollinger-Iten J, von Graevenitz A. (1992)
In vitro activities of Ro 40-6890 against 164 predominantly intestinal members of the families Enterobacteriaceae and Vibrionaceae.
Antimicrob Agents Chemother, 36 (12): 2835-8. [PMID:1482154]
3. Pfaller MA, Barry AL, Fuchs PC. (1993)
Antimicrobial activity and disk diffusion susceptibility testing of Ro 40-6890, the active metabolite of the new cephalosporin ester, Ro 41-3399.
Antimicrob Agents Chemother, 37 (4): 893-5. [PMID:8494387]
4. Wüst J, Hardegger U. (1992)
Comparative in vitro activity of Ro 40-6890, Ro 41-3399, and other antimicrobial agents against anaerobic bacteria.
Eur J Clin Microbiol Infect Dis, 11 (10): 946-9. [PMID:1486894]