2-Methyl-6-{[(4-nitro-3-trifluoromethyl-phenyl)-prop-2-ynyl-amino]-methyl}-3H-quinazolin-4-one

ID: ALA171180

PubChem CID: 135503923

Max Phase: Preclinical

Molecular Formula: C20H15F3N4O3

Molecular Weight: 416.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCN(Cc1ccc2nc(C)nc(O)c2c1)c1ccc([N+](=O)[O-])c(C(F)(F)F)c1

Standard InChI:  InChI=1S/C20H15F3N4O3/c1-3-8-26(14-5-7-18(27(29)30)16(10-14)20(21,22)23)11-13-4-6-17-15(9-13)19(28)25-12(2)24-17/h1,4-7,9-10H,8,11H2,2H3,(H,24,25,28)

Standard InChI Key:  PAGXQGCQFLMONT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    6.7542   -3.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8042   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9667   -2.8917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -2.9792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917   -4.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1417   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1875   -4.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8042   -3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9292   -3.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667   -2.9875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2625   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167   -2.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6541   -1.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4042   -3.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3625   -2.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917   -1.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542   -2.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8875   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5917   -5.0625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.7917   -5.0750    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.0125   -4.3292    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.8625   -2.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2375   -3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3458   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3 17  2  0
  4  7  1  0
  5  2  2  0
  6  9  1  0
  7  1  2  0
  8  1  1  0
  9 24  2  0
 10  6  2  0
 11  1  1  0
 12 11  2  0
 13 12  1  0
 14 28  1  0
 15  7  1  0
 16 14  3  0
 17 22  1  0
 18  4  1  0
 19  4  2  0
 20  2  1  0
 21 13  1  0
 22 21  1  0
 23 12  1  0
 24 29  1  0
 25  8  1  0
 26  8  1  0
 27  8  1  0
 28 13  1  0
 29 22  2  0
 30 10  1  0
 15 23  2  0
  3  9  1  0
  5 10  1  0
M  CHG  2   4   1  18  -1
M  END

Alternative Forms

1. Parent:

   

   ALA171180

   ---

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: 416.36

Molecular Weight (Monoisotopic): 416.1096

AlogP: 4.21

#Rotatable Bonds: 5

Polar Surface Area: 92.39

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.82

CX Basic pKa: 1.82

CX LogP: 5.29

CX LogD: 5.29

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.38

Np Likeness Score: -1.69

References

1. Jones TR, Varney MD, Webber SE, Lewis KK, Marzoni GP, Palmer CL, Kathardekar V, Welsh KM, Webber S, Matthews DA, Appelt K, Smith WW, Janson CA, Villafranca JE, Bacquet RJ, Howland EF, Booth CL, Herrmann SM, Ward RW, White J, Moomaw EW, Bartlett CA, Morse CA..  (1996)  Structure-based design of lipophilic quinazoline inhibitors of thymidylate synthase.,  39  (4): [PMID:8632414] [10.1021/jm9502652]

Source

Source(1):

• Scientific Literature