4-Amino-7-(beta-D-ribofuranosyl)-5-(thiophen-3-yl)-7H-pyrrolo[2,3-d]pyrimidine

ID: ALA1814770

Chembl Id: CHEMBL1814770

PubChem CID: 49784059

Max Phase: Preclinical

Molecular Formula: C15H16N4O4S

Molecular Weight: 348.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(-c1ccsc1)cn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C15H16N4O4S/c16-13-10-8(7-1-2-24-5-7)3-19(14(10)18-6-17-13)15-12(22)11(21)9(4-20)23-15/h1-3,5-6,9,11-12,15,20-22H,4H2,(H2,16,17,18)/t9-,11-,12-,15-/m1/s1

Standard InChI Key:  MTBJDLSSYZDTQX-SDBHATRESA-N

Alternative Forms

1. Parent:

   

   ALA1814770

   (2R,3R,4S,5R)-2-[4-amino-5-(3-thienyl)pyrrolo[2,3-d]pyrimidin-7-yl]-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

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: 348.38

Molecular Weight (Monoisotopic): 348.0892

AlogP: 0.35

#Rotatable Bonds: 3

Polar Surface Area: 126.65

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.46

CX Basic pKa: 6.36

CX LogP: 0.15

CX LogD: 0.11

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.54

Np Likeness Score: 0.09

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