ID: ALA1814769

Max Phase: Preclinical

Molecular Formula: C15H16N4O5

Molecular Weight: 332.32

Molecule Type: Small molecule

Representations

Canonical SMILES:  Nc1ncnc2c1c(-c1ccoc1)cn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C15H16N4O5/c16-13-10-8(7-1-2-23-5-7)3-19(14(10)18-6-17-13)15-12(22)11(21)9(4-20)24-15/h1-3,5-6,9,11-12,15,20-22H,4H2,(H2,16,17,18)/t9-,11-,12-,15-/m1/s1

Standard InChI Key:  OHWWSQOZMWAXFE-SDBHATRESA-N

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

Properties

Molecular Weight: 332.32

Molecular Weight (Monoisotopic): 332.1121

AlogP: -0.12

#Rotatable Bonds: 3

Polar Surface Area: 139.79

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.46

CX Basic pKa: 6.34

CX LogP: -0.49

CX LogD: -0.53

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.52

Np Likeness Score: 0.98

References

1. Bourderioux A, Naus P, Perlíková P, Pohl R, Pichová I, Votruba I, Dzubák P, Konecný P, Hajdúch M, Stray KM, Wang T, Ray AS, Feng JY, Birkus G, Cihlar T, Hocek M..  (2011)  Synthesis and significant cytostatic activity of 7-hetaryl-7-deazaadenosines.,  54  (15): [PMID:21711054] [10.1021/jm2005173]

2. Snášel J, Nauš P, Dostál J, Hnízda A, Fanfrlík J, Brynda J, Bourderioux A, Dušek M, Dvořáková H, Stolaříková J, Zábranská H, Pohl R, Konečný P, Džubák P, Votruba I, Hajdúch M, Rezáčová P, Veverka V, Hocek M, Pichová I..  (2014)  Structural basis for inhibition of mycobacterial and human adenosine kinase by 7-substituted 7-(Het)aryl-7-deazaadenine ribonucleosides.,  57  (20): [PMID:25259627] [10.1021/jm500497v]

Source

Source(1):

• Scientific Literature