((2R,3S,4R,5R)-5-(2-amino-7-benzyl-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

ID: ALA1094975

Chembl Id: CHEMBL1094975

PubChem CID: 136138688

Max Phase: Preclinical

Molecular Formula: C17H20N5O8P

Molecular Weight: 453.35

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  Nc1nc2c(c(=O)[nH]1)[n+](Cc1ccccc1)cn2[C@@H]1O[C@H](COP(=O)([O-])O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C17H20N5O8P/c18-17-19-14-11(15(25)20-17)21(6-9-4-2-1-3-5-9)8-22(14)16-13(24)12(23)10(30-16)7-29-31(26,27)28/h1-5,8,10,12-13,16,23-24H,6-7H2,(H4-,18,19,20,25,26,27,28)/t10-,12-,13-,16-/m1/s1

Standard InChI Key:  WMKJRKYLDWLLPS-XNIJJKJLSA-N

Alternative Forms

  1. Parent:

    ALA1094975

    ---
  2. Alternative Forms:

    ALA1094975

    ---

Associated Targets(Human)

EIF4E Tchem Eukaryotic translation initation factor (600 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Eif4e Eukaryotic translation initiation factor 4E (654 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EIF4E Eukaryotic translation initiation factor 4E (100 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 453.35Molecular Weight (Monoisotopic): 453.1049AlogP: -2.26#Rotatable Bonds: 6
Polar Surface Area: 199.86Molecular Species: ACIDHBA: 10HBD: 5
#RO5 Violations: HBA (Lipinski): 13HBD (Lipinski): 6#RO5 Violations (Lipinski): 2
CX Acidic pKa: 1.22CX Basic pKa: CX LogP: -5.12CX LogD: -7.47
Aromatic Rings: 3Heavy Atoms: 31QED Weighted: 0.20Np Likeness Score: 0.73

References

1. Jia Y, Chiu TL, Amin EA, Polunovsky V, Bitterman PB, Wagner CR..  (2010)  Design, synthesis and evaluation of analogs of initiation factor 4E (eIF4E) cap-binding antagonist Bn7-GMP.,  45  (4): [PMID:20060622] [10.1016/j.ejmech.2009.11.054]
2. Chen X, Kopecky DJ, Mihalic J, Jeffries S, Min X, Heath J, Deignan J, Lai S, Fu Z, Guimaraes C, Shen S, Li S, Johnstone S, Thibault S, Xu H, Cardozo M, Shen W, Walker N, Kayser F, Wang Z..  (2012)  Structure-guided design, synthesis, and evaluation of guanine-derived inhibitors of the eIF4E mRNA-cap interaction.,  55  (8): [PMID:22458568] [10.1021/jm300037x]
3. Golojuch S, Kopcial M, Strzelecka D, Kasprzyk R, Baran N, Sikorski PJ, Kowalska J, Jemielity J..  (2020)  Exploring tryptamine conjugates as pronucleotides of phosphate-modified 7-methylguanine nucleotides targeting cap-dependent translation.,  28  (13): [PMID:32362385] [10.1016/j.bmc.2020.115523]

Source