ID: ALA2064640

Max Phase: Preclinical

Molecular Formula: C22H21ClN6O3

Molecular Weight: 452.90

Molecule Type: Small molecule

Representations

Canonical SMILES:  CNC(=O)[C@@]12C[C@@H]1[C@@H](n1cnc3c(NC)nc(C#Cc4ccccc4Cl)nc31)[C@H](O)[C@@H]2O

Standard InChI:  InChI=1S/C22H21ClN6O3/c1-24-19-15-20(28-14(27-19)8-7-11-5-3-4-6-13(11)23)29(10-26-15)16-12-9-22(12,21(32)25-2)18(31)17(16)30/h3-6,10,12,16-18,30-31H,9H2,1-2H3,(H,25,32)(H,24,27,28)/t12-,16-,17+,18+,22+/m1/s1

Standard InChI Key:  HYTZGNCPPKEQEP-YWNJHDJRSA-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: 452.90

Molecular Weight (Monoisotopic): 452.1364

AlogP: 0.95

#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: 1.53

CX LogD: 1.53

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.44

Np Likeness Score: -0.06

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]

Source

Source(1):

• Scientific Literature