2-((6-chloroquinolin-4-yl)methyl)-7-(cyclopropylmethyl)-3-(1-methyl-1H-imidazol-5-yl)-5-(prop-2-ynyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

ID: ALA1652588

Chembl Id: CHEMBL1652588

PubChem CID: 44241626

Max Phase: Preclinical

Molecular Formula: C26H22ClN7O2

Molecular Weight: 499.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCn1c(=O)c2c(-c3cncn3C)n(Cc3ccnc4ccc(Cl)cc34)nc2n(CC2CC2)c1=O

Standard InChI:  InChI=1S/C26H22ClN7O2/c1-3-10-32-25(35)22-23(21-12-28-15-31(21)2)34(30-24(22)33(26(32)36)13-16-4-5-16)14-17-8-9-29-20-7-6-18(27)11-19(17)20/h1,6-9,11-12,15-16H,4-5,10,13-14H2,2H3

Standard InChI Key:  KESMOWDPGATUGY-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1652588

   2-[(6-Chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-3-(3-methylimidazol-4-yl)-5-prop-2-ynylpyrazolo[3,4-d]pyrimidine-4,6-dione

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: 499.96

Molecular Weight (Monoisotopic): 499.1524

AlogP: 3.05

#Rotatable Bonds: 6

Polar Surface Area: 92.53

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.66

CX LogP: 2.94

CX LogD: 2.94

Aromatic Rings: 5

Heavy Atoms: 36

QED Weighted: 0.33

Np Likeness Score: -1.41

References

1. de Jonge BL, Kutschke A, Uria-Nickelsen M, Kamp HD, Mills SD..  (2009)  Pyrazolopyrimidinediones are selective agents for Helicobacter pylori that suppress growth through inhibition of glutamate racemase (MurI).,  53  (8): [PMID:19433553] [10.1128/aac.00226-09]

2. Basarab GS, Hill P, Eyermann CJ, Gowravaram M, Käck H, Osimoni E..  (2012)  Design of inhibitors of Helicobacter pylori glutamate racemase as selective antibacterial agents: incorporation of imidazoles onto a core pyrazolopyrimidinedione scaffold to improve bioavailabilty.,  22  (17): [PMID:22877632] [10.1016/j.bmcl.2012.07.004]

3. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

Source

Source(2):

• Scientific Literature
• AstraZeneca Deposited Data