3-Phenylpropyl (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: ALA4096775

Chembl Id: CHEMBL4096775

PubChem CID: 137656204

Max Phase: Preclinical

Molecular Formula: C28H26ClN5O4S

Molecular Weight: 564.07

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)OCCCc3ccccc3)C[C@H]12

Standard InChI:  InChI=1S/C28H26ClN5O4S/c1-30-25-21-26(33-20(32-25)12-10-17-9-11-19(29)39-17)34(15-31-21)22-18-14-28(18,24(36)23(22)35)27(37)38-13-5-8-16-6-3-2-4-7-16/h2-4,6-7,9,11,15,18,22-24,35-36H,5,8,13-14H2,1H3,(H,30,32,33)/t18-,22-,23+,24+,28+/m1/s1

Standard InChI Key:  OXVZGJIJDLNINF-JIGPFOKVSA-N

Alternative Forms

1. Parent:

   

   ALA4096775

   ---

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: 564.07

Molecular Weight (Monoisotopic): 563.1394

AlogP: 3.44

#Rotatable Bonds: 7

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: 4.50

CX LogD: 4.50

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.18

Np Likeness Score: 0.12

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