ancremonam   Click here for help

GtoPdb Ligand ID: 13161

Synonyms: BOS-228 | LYS228
Compound class: Synthetic organic
Comment: Ancremonam is a monocyclic β-lactam (monobactam) antibacterial compound [2]. It has activity against carbapenem-resistant Enterobacteriaceae (CRE) and is stable against both metallo- and serine β-lactamases [1-2].
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 14
Hydrogen bond donors 4
Rotatable bonds 10
Topological polar surface area 264.27
Molecular weight 518.48
XLogP -2.42
No. Lipinski's rules broken 2
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 C1CC1(C(=O)O)O/N=C(/C2=CSC(=N2)N)\C(=O)N[C@H]3[C@@H](CN4CCOC4=O)N(C3=O)S(=O)(=O)O
Isomeric SMILES C1CC1(C(=O)O)O/N=C(/C2=CSC(=N2)N)\C(=O)N[C@H]3[C@H](N(C3=O)S(=O)(=O)O)CN4CCOC4=O
InChI InChI=1S/C16H18N6O10S2/c17-14-18-7(6-33-14)9(20-32-16(1-2-16)13(25)26)11(23)19-10-8(5-21-3-4-31-15(21)27)22(12(10)24)34(28,29)30/h6,8,10H,1-5H2,(H2,17,18)(H,19,23)(H,25,26)(H,28,29,30)/b20-9-/t8-,10+/m1/s1
InChI Key FWTGYTRQUBRVDW-NRABZWKMSA-N
References
1. Blais J, Lopez S, Li C, Ruzin A, Ranjitkar S, Dean CR, Leeds JA, Casarez A, Simmons RL, Reck F. (2018)
In Vitro Activity of LYS228, a Novel Monobactam Antibiotic, against Multidrug-Resistant Enterobacteriaceae.
Antimicrob Agents Chemother, 62 (10). [PMID:30038040]
2. Reck F, Bermingham A, Blais J, Capka V, Cariaga T, Casarez A, Colvin R, Dean CR, Fekete A, Gong W et al.. (2018)
Optimization of novel monobactams with activity against carbapenem-resistant Enterobacteriaceae - Identification of LYS228.
Bioorg Med Chem Lett, 28 (4): 748-755. [PMID:29336873]