ID: ALA3350631

Max Phase: Preclinical

Molecular Formula: C22H31N10O18P3

Molecular Weight: 816.46

Molecule Type: Small molecule

Representations

Canonical SMILES:  CO[C@H]1[C@@H](O)[C@H](n2c[n+](C)c3c(O)nc(N)nc32)O[C@@H]1COP(=O)(O)OP(=O)([O-])OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C22H31N10O18P3/c1-30-6-32(16-10(30)18(37)29-22(24)27-16)20-13(35)14(44-2)8(48-20)4-46-52(40,41)50-53(42,43)49-51(38,39)45-3-7-11(33)12(34)19(47-7)31-5-25-9-15(31)26-21(23)28-17(9)36/h5-8,11-14,19-20,33-35H,3-4H2,1-2H3,(H8-,23,24,26,27,28,29,36,37,38,39,40,41,42,43)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1

Standard InChI Key:  AIRSQUYUYJSIIM-XPWFQUROSA-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: 816.46

Molecular Weight (Monoisotopic): 816.1031

AlogP: -4.11

#Rotatable Bonds: 13

Polar Surface Area: 410.46

Molecular Species: ACID

HBA: 24

HBD: 9

#RO5 Violations: 3

HBA (Lipinski): 28

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.86

CX Basic pKa: 1.88

CX LogP: -9.01

CX LogD: -13.68

Aromatic Rings: 4

Heavy Atoms: 53

QED Weighted: 0.05

Np Likeness Score: 0.85

References

1. 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]

2. 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]

3. 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