ID: ALA2064645

Max Phase: Preclinical

Molecular Formula: C22H20F2N6O3

Molecular Weight: 454.44

Molecule Type: Small molecule

Representations

Canonical SMILES:  CNC(=O)[C@@]12C[C@@H]1[C@@H](n1cnc3c(NC)nc(C#Cc4ccc(F)c(F)c4)nc31)[C@H](O)[C@@H]2O

Standard InChI:  InChI=1S/C22H20F2N6O3/c1-25-19-15-20(29-14(28-19)6-4-10-3-5-12(23)13(24)7-10)30(9-27-15)16-11-8-22(11,21(33)26-2)18(32)17(16)31/h3,5,7,9,11,16-18,31-32H,8H2,1-2H3,(H,26,33)(H,25,28,29)/t11-,16-,17+,18+,22+/m1/s1

Standard InChI Key:  COVMIZBBIXKPJU-FJHPWZMNSA-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: 454.44

Molecular Weight (Monoisotopic): 454.1565

AlogP: 0.57

#Rotatable Bonds: 3

Polar Surface Area: 125.19

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.12

CX Basic pKa: 3.45

CX LogP: 1.26

CX LogD: 1.26

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.43

Np Likeness Score: -0.32

References

1. Tosh DK, Deflorian F, Phan K, Gao ZG, Wan TC, Gizewski E, Auchampach JA, Jacobson KA..  (2012)  Structure-guided design of A(3) adenosine receptor-selective nucleosides: combination of 2-arylethynyl and bicyclo[3.1.0]hexane substitutions.,  55  (10): [PMID:22559880] [10.1021/jm300396n]

2. Tosh DK, Finley A, Paoletta S, Moss SM, Gao ZG, Gizewski ET, Auchampach JA, Salvemini D, Jacobson KA..  (2014)  In vivo phenotypic screening for treating chronic neuropathic pain: modification of C2-arylethynyl group of conformationally constrained A3 adenosine receptor agonists.,  57  (23): [PMID:25422861] [10.1021/jm501021n]

3. Tosh DK, Janowsky A, Eshleman AJ, Warnick E, Gao ZG, Chen Z, Gizewski E, Auchampach JA, Salvemini D, Jacobson KA..  (2017)  Scaffold Repurposing of Nucleosides (Adenosine Receptor Agonists): Enhanced Activity at the Human Dopamine and Norepinephrine Sodium Symporters.,  60  (7): [PMID:28319392] [10.1021/acs.jmedchem.7b00141]

Source

Source(1):

• Scientific Literature