4-Amino-5-(1H-pyrrol-3-yl)-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

ID: ALA1814773

Chembl Id: CHEMBL1814773

PubChem CID: 49784133

Max Phase: Preclinical

Molecular Formula: C15H17N5O4

Molecular Weight: 331.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(-c1cc[nH]c1)cn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C15H17N5O4/c16-13-10-8(7-1-2-17-3-7)4-20(14(10)19-6-18-13)15-12(23)11(22)9(5-21)24-15/h1-4,6,9,11-12,15,17,21-23H,5H2,(H2,16,18,19)/t9-,11-,12-,15-/m1/s1

Standard InChI Key:  UPQSMPXNDMYOTB-SDBHATRESA-N

Alternative Forms

1. Parent:

   

   ALA1814773

   (2R,3R,4S,5R)-2-[4-amino-5-(1H-pyrrol-3-yl)pyrrolo[2,3-d]pyrimidin-7-yl]-5-(hydroxymethyl)oxolane-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: 331.33

Molecular Weight (Monoisotopic): 331.1281

AlogP: -0.38

#Rotatable Bonds: 3

Polar Surface Area: 142.44

Molecular Species: NEUTRAL

HBA: 8

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.46

CX Basic pKa: 6.35

CX LogP: -0.55

CX LogD: -0.59

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.44

Np Likeness Score: 0.84

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