1-cyclopentyl-5-(6-oxo-1,6-dihydropyrimidin-2-yl)-1H-indole-3-carbonitrile

ID: ALA5208608

PubChem CID: 156780239

Max Phase: Preclinical

Molecular Formula: C18H16N4O

Molecular Weight: 304.35

Names and Identifiers

Canonical SMILES:  N#Cc1cn(C2CCCC2)c2ccc(-c3nccc(O)n3)cc12

Standard InChI:  InChI=1S/C18H16N4O/c19-10-13-11-22(14-3-1-2-4-14)16-6-5-12(9-15(13)16)18-20-8-7-17(23)21-18/h5-9,11,14H,1-4H2,(H,20,21,23)

Standard InChI Key:  DCDHGYPAMODFAC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   -2.6673    1.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9527    2.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2409    1.6007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2409    0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9510    0.3637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6673    0.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5262    0.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1885    0.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9006    0.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9006   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1902   -0.8740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5262   -0.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6837   -0.7080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1759   -0.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7050    0.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9186    1.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1322    2.2077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8973   -1.5051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9527    2.8378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6673   -1.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6241   -2.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8275   -2.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782   -2.1460    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
  6  5  2  0
  1  6  1  0
  4  7  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
 11 10  1  0
 12 11  2  0
  7 12  1  0
 10 13  1  0
 13 14  1  0
 15 14  2  0
  9 15  1  0
 16 15  1  0
 16 17  3  0
 13 18  1  0
  2 19  1  0
 20 18  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5208608

   ---

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: 304.35

Molecular Weight (Monoisotopic): 304.1324

AlogP: 3.79

#Rotatable Bonds: 2

Polar Surface Area: 74.73

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.12

CX Basic pKa: 0.88

CX LogP: 4.23

CX LogD: 4.23

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.78

Np Likeness Score: -1.22

References

1. Zhang B, Duan Y, Yang Y, Mao Q, Lin F, Gao J, Dai X, Zhang P, Li Q, Li J, Dai R, Wang S..  (2022)  Design, synthesis, and biological evaluation of N-(3-cyano-1H-indol-5/6-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxamides and 5-(6-oxo-1,6-dihydropyrimidin-2-yl)-1H-indole-3-carbonitriles as novel xanthine oxidase inhibitors.,  227  [PMID:34688012] [10.1016/j.ejmech.2021.113928]

Source

Source(1):

• Scientific Literature