2-(3-cyano-4-isopentyloxy)phenylpyrimidine-4-carboxylic acid

ID: ALA5206769

PubChem CID: 168295661

Max Phase: Preclinical

Molecular Formula: C17H17N3O3

Molecular Weight: 311.34

Names and Identifiers

Canonical SMILES:  CC(C)CCOc1ccc(-c2nccc(C(=O)O)n2)cc1C#N

Standard InChI:  InChI=1S/C17H17N3O3/c1-11(2)6-8-23-15-4-3-12(9-13(15)10-18)16-19-7-5-14(20-16)17(21)22/h3-5,7,9,11H,6,8H2,1-2H3,(H,21,22)

Standard InChI Key:  PXZNVNZEGWNOKM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   -0.7133    0.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0012    0.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130    0.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130   -0.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0030   -0.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7133   -0.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -0.8261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -1.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1426   -2.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1426   -2.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8572   -3.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -3.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0030   -1.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0030   -2.4719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4277    0.8279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4279    1.6532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1408    2.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8556    1.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8572    0.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1454    0.4136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1408    2.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4262    3.3016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8554    3.3016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  5 13  1  0
 13 14  3  0
 15  3  1  0
 16 15  2  0
 17 16  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 15 20  1  0
 17 21  1  0
 21 22  1  0
 21 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5206769

   ---

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: 311.34

Molecular Weight (Monoisotopic): 311.1270

AlogP: 3.14

#Rotatable Bonds: 6

Polar Surface Area: 96.10

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.78

CX Basic pKa: 5.03

CX LogP: 2.10

CX LogD: 0.19

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.88

Np Likeness Score: -1.07

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