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

ID: ALA1094974

Chembl Id: CHEMBL1094974

PubChem CID: 136168051

Max Phase: Preclinical

Molecular Formula: C11H17N5O11P2

Molecular Weight: 457.23

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H17N5O11P2/c1-15-3-16(8-5(15)9(19)14-11(12)13-8)10-7(18)6(17)4(26-10)2-25-29(23,24)27-28(20,21)22/h3-4,6-7,10,17-18H,2H2,1H3,(H5-,12,13,14,19,20,21,22,23,24)/t4-,6-,7-,10-/m1/s1

Standard InChI Key:  SBASPRRECYVBRF-KQYNXXCUSA-N

Alternative Forms

1. Parent:

   

   ALA1094974

   ---

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: 457.23

Molecular Weight (Monoisotopic): 457.0400

AlogP: -3.66

#Rotatable Bonds: 6

Polar Surface Area: 246.39

Molecular Species: ACID

HBA: 12

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.77

CX Basic pKa: 0.31

CX LogP: -7.41

CX LogD: -11.12

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.18

Np Likeness Score: 1.18

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. 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]

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

Source(1):

• Scientific Literature