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

ID: ALA1097198

Chembl Id: CHEMBL1097198

PubChem CID: 136168052

Max Phase: Preclinical

Molecular Formula: C11H16N5O8P

Molecular Weight: 377.25

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H16N5O8P/c1-15-3-16(8-5(15)9(19)14-11(12)13-8)10-7(18)6(17)4(24-10)2-23-25(20,21)22/h3-4,6-7,10,17-18H,2H2,1H3,(H4-,12,13,14,19,20,21,22)/t4-,6-,7-,10-/m1/s1

Standard InChI Key:  AOKQNZVJJXPUQA-KQYNXXCUSA-N

Alternative Forms

1. Parent:

   

   ALA1097198

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2. Alternative Forms:

   

   ALA1097198

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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

Calculated Properties

Molecular Weight: 377.25

Molecular Weight (Monoisotopic): 377.0736

AlogP: -3.77

#Rotatable Bonds: 4

Polar Surface Area: 199.86

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.22

CX Basic pKa: 0.27

CX LogP: -7.11

CX LogD: -9.19

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.26

Np Likeness Score: 1.16

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. 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]

4. Kozarski M, Kubacka D, Wojtczak BA, Kasprzyk R, Baranowski MR, Kowalska J..  (2018)  7-Methylguanosine monophosphate analogues with 5'-(1,2,3-triazoyl) moiety: Synthesis and evaluation as the inhibitors of cNIIIB nucleotidase.,  26  (1): [PMID:29195795] [10.1016/j.bmc.2017.11.032]

5. 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

Source(1):

• Scientific Literature