Methyl (1S,2R,3S,4R,5S)-4-(2-((5-Bromothiophen-2-yl)ethynyl)-6-(methylamino)-9H-purin-9-yl)-2,3-dihydroxybicyclo[3.1.0]hexane-1-carboxylate

ID: ALA4071830

Chembl Id: CHEMBL4071830

PubChem CID: 137639266

Max Phase: Preclinical

Molecular Formula: C20H18BrN5O4S

Molecular Weight: 504.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1nc(C#Cc2ccc(Br)s2)nc2c1ncn2[C@H]1[C@H](O)[C@H](O)[C@]2(C(=O)OC)C[C@H]12

Standard InChI:  InChI=1S/C20H18BrN5O4S/c1-22-17-13-18(25-12(24-17)6-4-9-3-5-11(21)31-9)26(8-23-13)14-10-7-20(10,19(29)30-2)16(28)15(14)27/h3,5,8,10,14-16,27-28H,7H2,1-2H3,(H,22,24,25)/t10-,14-,15+,16+,20+/m1/s1

Standard InChI Key:  RJBNRAHSRNPIGX-AQPYCOETSA-N

Alternative Forms

1. Parent:

   

   ALA4071830

   ---

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: 504.37

Molecular Weight (Monoisotopic): 503.0263

AlogP: 1.55

#Rotatable Bonds: 3

Polar Surface Area: 122.39

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.12

CX Basic pKa: 3.41

CX LogP: 2.29

CX LogD: 2.29

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.36

Np Likeness Score: 0.37

References

1. 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