(1R,2R,3S,4R,5S)-4-(2-Chloro-6-((dicyclopropylmethyl)amino)-9H-purin-9-yl)-1-(hydroxymethyl)bicyclo[3.1.0]hexane-2,3-diol

ID: ALA3923870

Chembl Id: CHEMBL3923870

PubChem CID: 134141831

Max Phase: Preclinical

Molecular Formula: C19H24ClN5O3

Molecular Weight: 405.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@@]12C[C@@H]1[C@@H](n1cnc3c(NC(C4CC4)C4CC4)nc(Cl)nc31)[C@H](O)[C@@H]2O

Standard InChI:  InChI=1S/C19H24ClN5O3/c20-18-23-16(22-11(8-1-2-8)9-3-4-9)12-17(24-18)25(7-21-12)13-10-5-19(10,6-26)15(28)14(13)27/h7-11,13-15,26-28H,1-6H2,(H,22,23,24)/t10-,13-,14+,15+,19+/m1/s1

Standard InChI Key:  HOGXFHNYQVRCAK-DRYZDSLUSA-N

Alternative Forms

1. Parent:

   

   ALA3923870

   ---

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: 405.89

Molecular Weight (Monoisotopic): 405.1568

AlogP: 1.36

#Rotatable Bonds: 6

Polar Surface Area: 116.32

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.24

CX Basic pKa: 1.73

CX LogP: 0.65

CX LogD: 0.65

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: 0.46

References

1. Tosh DK, Ciancetta A, Warnick E, Crane S, Gao ZG, Jacobson KA..  (2016)  Structure-Based Scaffold Repurposing for G Protein-Coupled Receptors: Transformation of Adenosine Derivatives into 5HT2B/5HT2C Serotonin Receptor Antagonists.,  59  (24): [PMID:27933810] [10.1021/acs.jmedchem.6b01183]

2. Tosh DK,Toti KS,Hurst BL,Julander JG,Jacobson KA.  (2020)  Structure activity relationship of novel antiviral nucleosides against Enterovirus A71.,  30  (23): [PMID:33031923] [10.1016/j.bmcl.2020.127599]

Source

Source(1):

• Scientific Literature