ID: ALA515570

Max Phase: Preclinical

Molecular Formula: C20H21N7O4

Molecular Weight: 423.43

Molecule Type: Small molecule

Representations

Canonical SMILES:  Nc1ncnc2c1nc(NCc1ccc3ncccc3c1)n2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C20H21N7O4/c21-17-14-18(25-9-24-17)27(19-16(30)15(29)13(8-28)31-19)20(26-14)23-7-10-3-4-12-11(6-10)2-1-5-22-12/h1-6,9,13,15-16,19,28-30H,7-8H2,(H,23,26)(H2,21,24,25)/t13-,15-,16-,19-/m1/s1

Standard InChI Key:  ZPAVHMFARWZWPX-NVQRDWNXSA-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: 423.43

Molecular Weight (Monoisotopic): 423.1655

AlogP: 0.18

#Rotatable Bonds: 5

Polar Surface Area: 164.46

Molecular Species: NEUTRAL

HBA: 11

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.45

CX Basic pKa: 4.77

CX LogP: -0.05

CX LogD: -0.05

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.30

Np Likeness Score: -0.04

References

1. Williamson DS, Borgognoni J, Clay A, Daniels Z, Dokurno P, Drysdale MJ, Foloppe N, Francis GL, Graham CJ, Howes R, Macias AT, Murray JB, Parsons R, Shaw T, Surgenor AE, Terry L, Wang Y, Wood M, Massey AJ..  (2009)  Novel adenosine-derived inhibitors of 70 kDa heat shock protein, discovered through structure-based design.,  52  (6): [PMID:19256508] [10.1021/jm801627a]

2. Macias AT, Williamson DS, Allen N, Borgognoni J, Clay A, Daniels Z, Dokurno P, Drysdale MJ, Francis GL, Graham CJ, Howes R, Matassova N, Murray JB, Parsons R, Shaw T, Surgenor AE, Terry L, Wang Y, Wood M, Massey AJ..  (2011)  Adenosine-derived inhibitors of 78 kDa glucose regulated protein (Grp78) ATPase: insights into isoform selectivity.,  54  (12): [PMID:21526763] [10.1021/jm101625x]

3. Cheeseman MD, Westwood IM, Barbeau O, Rowlands M, Dobson S, Jones AM, Jeganathan F, Burke R, Kadi N, Workman P, Collins I, van Montfort RL, Jones K..  (2016)  Exploiting Protein Conformational Change to Optimize Adenosine-Derived Inhibitors of HSP70.,  59  (10): [PMID:27119979] [10.1021/acs.jmedchem.5b02001]

Source

Source(1):

• Scientific Literature