2-(3-cyano-4-(cyclohexylmethoxy))phenylpyrimidine-5-carboxylic acid

ID: ALA5203944

PubChem CID: 168293752

Max Phase: Preclinical

Molecular Formula: C19H19N3O3

Molecular Weight: 337.38

Names and Identifiers

Canonical SMILES:  N#Cc1cc(-c2ncc(C(=O)O)cn2)ccc1OCC1CCCCC1

Standard InChI:  InChI=1S/C19H19N3O3/c20-9-15-8-14(18-21-10-16(11-22-18)19(23)24)6-7-17(15)25-12-13-4-2-1-3-5-13/h6-8,10-11,13H,1-5,12H2,(H,23,24)

Standard InChI Key:  LTOBJEZKUDLRAI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -0.3553    1.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3566    0.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3566   -0.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3534   -0.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0698   -0.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0712    1.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0714    1.8595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7843    2.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4992    1.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007    1.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7889    0.6199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3534   -1.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3534   -2.2656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2137    2.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2137    3.0953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9284    1.8575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7844   -0.6197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7844   -1.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4991   -1.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4991   -2.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2137   -1.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2137   -3.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284   -1.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284   -2.6827    0.0000 C   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
  1  6  1  0
  6  5  2  0
  7  3  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
 11 10  1  0
  7 12  1  0
 12 11  2  0
  5 13  1  0
 13 14  3  0
 10 15  1  0
 15 16  2  0
 15 17  1  0
  6 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 21 23  1  0
 22 24  1  0
 23 25  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5203944

   ---

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: 337.38

Molecular Weight (Monoisotopic): 337.1426

AlogP: 3.67

#Rotatable Bonds: 5

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: 3.84

CX Basic pKa: 1.02

CX LogP: 3.64

CX LogD: 0.37

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.89

Np Likeness Score: -1.10

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