6-[3-cyano-4-(4-methylbenzyloxy)phenyl]-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one

ID: ALA5172810

Chembl Id: CHEMBL5172810

PubChem CID: 156705018

Max Phase: Preclinical

Molecular Formula: C20H15N5O2

Molecular Weight: 357.37

Names and Identifiers

Canonical SMILES:  Cc1ccc(COc2ccc(-c3ncc4c(=O)[nH][nH]c4n3)cc2C#N)cc1

Standard InChI:  InChI=1S/C20H15N5O2/c1-12-2-4-13(5-3-12)11-27-17-7-6-14(8-15(17)9-21)18-22-10-16-19(23-18)24-25-20(16)26/h2-8,10H,11H2,1H3,(H2,22,23,24,25,26)

Standard InChI Key:  QUBQJNNFJHIQGZ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA5172810

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Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 357.37

Molecular Weight (Monoisotopic): 357.1226

AlogP: 3.07

#Rotatable Bonds: 4

Polar Surface Area: 107.45

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.51

CX Basic pKa: 3.71

CX LogP: 4.37

CX LogD: 4.37

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.58

Np Likeness Score: -1.22

References

1. Zhao J, Mao Q, Lin F, Zhang B, Sun M, Zhang T, Wang S..  (2022)  Intramolecular hydrogen bond interruption and scaffold hopping of TMC-5 led to 2-(4-alkoxy-3-cyanophenyl)pyrimidine-4/5-carboxylic acids and 6-(4-alkoxy-3-cyanophenyl)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-ones as potent pyrimidine-based xanthine oxidase inhibitors.,  229  [PMID:34992040] [10.1016/j.ejmech.2021.114086]

Source

Source(1):

• Scientific Literature