ID: ALA3351000

Max Phase: Preclinical

Molecular Formula: C21H29N10O18P3

Molecular Weight: 802.44

Molecule Type: Small molecule

Representations

Canonical SMILES:  C[n+]1cn([C@@H]2O[C@H](COP(=O)(O)OP(=O)([O-])OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(=O)[nH]c(N)nc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)c2nc(N)nc(O)c21

Standard InChI:  InChI=1S/C21H29N10O18P3/c1-29-5-31(15-9(29)17(37)28-21(23)26-15)19-13(35)11(33)7(47-19)3-45-51(40,41)49-52(42,43)48-50(38,39)44-2-6-10(32)12(34)18(46-6)30-4-24-8-14(30)25-20(22)27-16(8)36/h4-7,10-13,18-19,32-35H,2-3H2,1H3,(H8-,22,23,25,26,27,28,36,37,38,39,40,41,42,43)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1

Standard InChI Key:  FHHZHGZBHYYWTG-INFSMZHSSA-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: 802.44

Molecular Weight (Monoisotopic): 802.0874

AlogP: -4.77

#Rotatable Bonds: 12

Polar Surface Area: 421.46

Molecular Species: ACID

HBA: 24

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 28

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.86

CX Basic pKa: 1.88

CX LogP: -9.66

CX LogD: -14.32

Aromatic Rings: 4

Heavy Atoms: 52

QED Weighted: 0.05

Np Likeness Score: 0.70

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. Rydzik AM, Kulis M, Lukaszewicz M, Kowalska J, Zuberek J, Darzynkiewicz ZM, Darzynkiewicz E, Jemielity J..  (2012)  Synthesis and properties of mRNA cap analogs containing imidodiphosphate moiety--fairly mimicking natural cap structure, yet resistant to enzymatic hydrolysis.,  20  (5): [PMID:22316555] [10.1016/j.bmc.2012.01.013]

3. Warminski M, Kowalska J, Buck J, Zuberek J, Lukaszewicz M, Nicola C, Kuhn AN, Sahin U, Darzynkiewicz E, Jemielity J..  (2013)  The synthesis of isopropylidene mRNA cap analogs modified with phosphorothioate moiety and their evaluation as promoters of mRNA translation.,  23  (13): [PMID:23726029] [10.1016/j.bmcl.2013.05.001]

4. 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]

5.  (2009)  Inhibition of DCPS, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data