ID: ALA1094973

Max Phase: Preclinical

Molecular Formula: C11H18N5O14P3

Molecular Weight: 537.21

Molecule Type: Small molecule

Representations

Canonical SMILES:  C[n+]1cn([C@@H]2O[C@H](COP(=O)([O-])OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c2nc(N)[nH]c(=O)c21

Standard InChI:  InChI=1S/C11H18N5O14P3/c1-15-3-16(8-5(15)9(19)14-11(12)13-8)10-7(18)6(17)4(28-10)2-27-32(23,24)30-33(25,26)29-31(20,21)22/h3-4,6-7,10,17-18H,2H2,1H3,(H6-,12,13,14,19,20,21,22,23,24,25,26)/t4-,6-,7-,10-/m1/s1

Standard InChI Key:  DKVRNHPCAOHRSI-KQYNXXCUSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 537.21

Molecular Weight (Monoisotopic): 537.0063

AlogP: -3.54

#Rotatable Bonds: 8

Polar Surface Area: 292.92

Molecular Species: ACID

HBA: 14

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 19

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.90

CX Basic pKa: 0.22

CX LogP: -8.10

CX LogD: -13.91

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.13

Np Likeness Score: 1.20

References

1. Kowalska J, Lukaszewicz M, Zuberek J, Ziemniak M, Darzynkiewicz E, Jemielity J..  (2009)  Phosphorothioate analogs of m7GTP are enzymatically stable inhibitors of cap-dependent translation.,  19  (7): [PMID:19269171] [10.1016/j.bmcl.2009.02.053]

2. 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]

3. 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]

4. Piecyk K, Davis RE, Jankowska-Anyszka M..  (2012)  Synthesis of N²-modified 7-methylguanosine 5'-monophosphates as nematode translation inhibitors.,  20  (15): [PMID:22748379] [10.1016/j.bmc.2012.05.078]

5. Ziemniak M, Kowalska J, Lukaszewicz M, Zuberek J, Wnek K, Darzynkiewicz E, Jemielity J..  (2015)  Phosphate-modified analogues of m(7)GTP and m(7)Gppppm(7)G-Synthesis and biochemical properties.,  23  (17): [PMID:26264844] [10.1016/j.bmc.2015.07.052]

Source

Source(1):

• Scientific Literature