eAmSPC 2593   Click here for help

GtoPdb Ligand ID: 13565

Compound class: Synthetic organic
Comment: eAmSPC 2593 is the lead from a new class of N-ethylene linked aminomethyl spectinomycins (eAmSPCs), discovered following modification of spectinomycin, and with promising antimycobacterial activity [2]. The structure is claimed in patent WO2015048692A1 filed by St. Jude Children's Research Hospital [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 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 7
Rotatable bonds 7
Topological polar surface area 144.7
Molecular weight 485.55
XLogP -0.69
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 C[C@@H]1C[C@@](CNCCC2=CC=C(C=C2)F)([C@]3([C@@H](O1)O[C@@H]4[C@H]([C@@H]([C@@H]([C@@H]([C@H]4O3)NC)O)NC)O)O)O
Isomeric SMILES C[C@@H]1C[C@]([C@]2([C@@H](O1)O[C@@H]3[C@H]([C@@H]([C@@H]([C@@H]([C@H]3O2)NC)O)NC)O)O)(CNCCC4=CC=C(C=C4)F)O
InChI InChI=1S/C23H36FN3O7/c1-12-10-22(30,11-27-9-8-13-4-6-14(24)7-5-13)23(31)21(32-12)33-20-18(29)15(25-2)17(28)16(26-3)19(20)34-23/h4-7,12,15-21,25-31H,8-11H2,1-3H3/t12-,15-,16+,17+,18+,19-,20-,21+,22-,23-/m1/s1
InChI Key KRCLSDQUEUBIKY-LLHOOWCXSA-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/)
References
1. Lee RE, Waidyarachchi SL, Bruhn DF, Liu J, Zheng Z, Rosch JW. (2015)
Aryl substituted aminomethyl spectinomycin analogs as antibacterial agents.
Patent number: WO2015048692A1. Assignee: St. Jude Children's Research Hospital. Priority date: 29/09/2013. Publication date: 02/04/2015.
2. Phelps GA, Cheramie MN, Fernando DM, Selchow P, Meyer CJ, Waidyarachchi SL, Dharuman S, Liu J, Meuli M, Molin MD et al.. (2024)
Development of 2nd generation aminomethyl spectinomycins that overcome native efflux in Mycobacterium abscessus.
Proc Natl Acad Sci U S A, 121 (2): e2314101120. [PMID:38165935]