5-(2-((6-chloroquinolin-4-yl)methyl)-7-(cyclopropylmethyl)-5-methyl-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl)-1-methyl-1H-pyrrole-3-carbonitrile

ID: ALA257600

Chembl Id: CHEMBL257600

Cas Number: 946411-72-9

PubChem CID: 24884488

Max Phase: Preclinical

Molecular Formula: C26H22ClN7O2

Molecular Weight: 499.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc(C#N)cc1-c1c2c(=O)n(C)c(=O)n(CC3CC3)c2nn1Cc1ccnc2ccc(Cl)cc12

Standard InChI:  InChI=1S/C26H22ClN7O2/c1-31-12-16(11-28)9-21(31)23-22-24(33(13-15-3-4-15)26(36)32(2)25(22)35)30-34(23)14-17-7-8-29-20-6-5-18(27)10-19(17)20/h5-10,12,15H,3-4,13-14H2,1-2H3

Standard InChI Key:  CFJFLGFKZVSNPA-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA257600

   5-{2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-5-methyl-4,6-dioxo-2H,4H,5H,6H,7H-pyrazolo[3,4-d]pyrimidin-3-yl}-1-methyl-1H-pyrrole-3-carbonitrile

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: 3.43

#Rotatable Bonds: 5

Polar Surface Area: 103.43

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.72

CX LogP: 3.77

CX LogD: 3.77

Aromatic Rings: 5

Heavy Atoms: 36

QED Weighted: 0.37

Np Likeness Score: -1.41

References

1. Lundqvist T, Fisher SL, Kern G, Folmer RH, Xue Y, Newton DT, Keating TA, Alm RA, de Jonge BL..  (2007)  Exploitation of structural and regulatory diversity in glutamate racemases.,  447  (7146): [PMID:17568739] [10.1038/nature05689]

2. Basarab GS, Hill PJ, Rastagar A, Webborn PJ..  (2008)  Design of Helicobacter pylori glutamate racemase inhibitors as selective antibacterial agents: a novel pro-drug approach to increase exposure.,  18  (16): [PMID:18640833] [10.1016/j.bmcl.2008.06.092]

3. 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]

4. 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]

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

6. Ghobadi E, Ghanbarimasir Z, Emami S..  (2021)  A review on the structures and biological activities of anti-Helicobacter pylori agents.,  223  [PMID:34218084] [10.1016/j.ejmech.2021.113669]

Source

Source(2):

• Scientific Literature
• AstraZeneca Deposited Data