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Harnessing RIBOnucleic acid - Small molecules Structures

Compound FFO

Identifiers

  • Canonical SMILES: 
    NC1=NC2=C(N(C=O)[C@@H](CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CN2)C(=O)N1
  • IUPAC name: 
    N-[4-({[(6S)-2-amino-5-formyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzoyl]-L-glutamic acid
  • InChi: 
    InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)/t12-,13-/m0/s1
  • InChiKey: 
    VVIAGPKUTFNRDU-STQMWFEESA-N
  • SMARTS: 
    [#7]-[#6]1:[#7]:[#6]2:[#6](-[#7](-[#6]=[#8])-[#6@@H](-[#6]-[#7]-[#6]3:[#6]:[#6]:[#6](:[#6]:[#6]:3)-[#6](=[#8])-[#7]-[#6@@H](-[#6]-[#6]-[#6](-[#8])=[#8])-[#6](-[#8])=[#8])-[#6]-[#7]-2):[#6](=[#8]):[#7]:1

Chemistry rules

Lipinski's RO5 Veber Pfizer's 3/75

External links

PubChem Logo 149436 ChEMBL Logo CHEMBL1908841 PDB Logo FFO DrugBank Logo DB11596

RNA-SM complexes

PDB code Deposition date Reference publication
3sd3 June 8, 2011 Trausch Jeremiah J., Ceres Pablo, Reyes Francis E., Batey Robert T.. 2011. The Structure of a Tetrahydrofolate-Sensing Riboswitch Reveals Two Ligand Binding Sites in a Single Aptamer Structure
3suh July 11, 2011 Huang Lili, Ishibe-Murakami Satoko, Patel Dinshaw J., Serganov Alexander. 2011. Long-range pseudoknot interactions dictate the regulatory response in the tetrahydrofolate riboswitch Proceedings of the National Academy of Sciences
4lvv July 26, 2013 Trausch Jeremiah J., Batey Robert T.. 2014. A Disconnect between High-Affinity Binding and Efficient Regulation by Antifolates and Purines in the Tetrahydrofolate Riboswitch Chemistry & Biology
4lvv July 26, 2013 Trausch Jeremiah J., Batey Robert T.. 2014. A Disconnect between High-Affinity Binding and Efficient Regulation by Antifolates and Purines in the Tetrahydrofolate Riboswitch Chemistry & Biology

Physicochemical filters

Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 473.17 g/mol
HBA 9
HBD 7
HBA + HBD
AlogP -0.73
TPSA 219.84
RB 10

Radar chart