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

ID: ALA4089071

Chembl Id: CHEMBL4089071

PubChem CID: 137644452

Max Phase: Preclinical

Molecular Formula: C26H22ClN5O4S

Molecular Weight: 536.01

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1nc(C#Cc2ccc(Cl)s2)nc2c1ncn2[C@H]1[C@H](O)[C@H](O)[C@]2(C(=O)OCc3ccccc3)C[C@H]12

Standard InChI:  InChI=1S/C26H22ClN5O4S/c1-28-23-19-24(31-18(30-23)10-8-15-7-9-17(27)37-15)32(13-29-19)20-16-11-26(16,22(34)21(20)33)25(35)36-12-14-5-3-2-4-6-14/h2-7,9,13,16,20-22,33-34H,11-12H2,1H3,(H,28,30,31)/t16-,20-,21+,22+,26+/m1/s1

Standard InChI Key:  FWBKOXGBMUBDHS-CSTWGOEFSA-N

Alternative Forms

1. Parent:

   

   ALA4089071

   ---

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: 536.01

Molecular Weight (Monoisotopic): 535.1081

AlogP: 3.01

#Rotatable Bonds: 5

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: 3.81

CX LogD: 3.81

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.26

Np Likeness Score: 0.07

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