(1S,2R,3S,4R,5S)-2,3-Dihydroxy-N-methyl-4-(6-(phenethylamino)-2-(phenylethynyl)-9H-purin-9-yl)bicyclo[3.1.0]hexane-1-carboxamide

ID: ALA2402024

Chembl Id: CHEMBL2402024

PubChem CID: 71764237

Max Phase: Preclinical

Molecular Formula: C29H28N6O3

Molecular Weight: 508.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)[C@@]12C[C@@H]1[C@@H](n1cnc3c(NCCc4ccccc4)nc(C#Cc4ccccc4)nc31)[C@H](O)[C@@H]2O

Standard InChI:  InChI=1S/C29H28N6O3/c1-30-28(38)29-16-20(29)23(24(36)25(29)37)35-17-32-22-26(31-15-14-19-10-6-3-7-11-19)33-21(34-27(22)35)13-12-18-8-4-2-5-9-18/h2-11,17,20,23-25,36-37H,14-16H2,1H3,(H,30,38)(H,31,33,34)/t20-,23-,24+,25+,29+/m1/s1

Standard InChI Key:  XHVZGOCXMKSHJQ-YUBGWGQWSA-N

Alternative Forms

1. Parent:

   

   ALA2402024

   (1S,2R,3S,4R,5S)-2,3-dihydroxy-N-methyl-4-[6-(2-phenylethylamino)-2-(2-phenylethynyl)purin-9-yl]bicyclo[3.1.0]hexane-1-carboxamide

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: 508.58

Molecular Weight (Monoisotopic): 508.2223

AlogP: 1.91

#Rotatable Bonds: 6

Polar Surface Area: 125.19

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.12

CX Basic pKa: 3.42

CX LogP: 2.96

CX LogD: 2.96

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.29

Np Likeness Score: -0.08

References

1. Paoletta S, Tosh DK, Finley A, Gizewski ET, Moss SM, Gao ZG, Auchampach JA, Salvemini D, Jacobson KA..  (2013)  Rational design of sulfonated A3 adenosine receptor-selective nucleosides as pharmacological tools to study chronic neuropathic pain.,  56  (14): [PMID:23789857] [10.1021/jm4007966]

2. Tosh DK, Salmaso V, Campbell RG, Rao H, Bitant A, Pottie E, Stove CP, Liu N, Gavrilova O, Gao ZG, Auchampach JA, Jacobson KA..  (2022)  A₃ adenosine receptor agonists containing dopamine moieties for enhanced interspecies affinity.,  228  [PMID:34844790] [10.1016/j.ejmech.2021.113983]

Source

Source(1):

• Scientific Literature