1-{7-Chloro-3-methyl-4-oxo-6-[(prop-2-ynyl-{4-[(pyridin-3-ylmethyl)-carbamoyl]-phenyl}-amino)-methyl]-3,4-dihydro-quinazolin-2-ylmethyl}-pyrrolidine-2-carboxylic acid methyl ester

ID: ALA333693

PubChem CID: 11017534

Max Phase: Preclinical

Molecular Formula: C33H33ClN6O4

Molecular Weight: 613.12

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCN(Cc1cc2c(=O)n(C)c(CN3CCC[C@H]3C(=O)OC)nc2cc1Cl)c1ccc(C(=O)NCc2cccnc2)cc1

Standard InChI:  InChI=1S/C33H33ClN6O4/c1-4-14-39(25-11-9-23(10-12-25)31(41)36-19-22-7-5-13-35-18-22)20-24-16-26-28(17-27(24)34)37-30(38(2)32(26)42)21-40-15-6-8-29(40)33(43)44-3/h1,5,7,9-13,16-18,29H,6,8,14-15,19-21H2,2-3H3,(H,36,41)/t29-/m0/s1

Standard InChI Key:  FKQXANKLFGKMMO-LJAQVGFWSA-N

Molfile:  

     RDKit          2D

 44 48  0  0  1  0  0  0  0  0999 V2000
    1.3042   -2.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3042   -3.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250   -2.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -3.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250   -3.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5875   -4.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -2.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5875   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4375   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8667   -2.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500   -3.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0750   -4.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8625   -4.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5750   -2.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2792   -0.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9875   -0.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5792   -1.7667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -0.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0417   -2.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4000   -2.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0792   -2.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0375   -3.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7000   -0.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6250   -1.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6292   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8042   -1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8042   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0042   -1.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2917   -2.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5875   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8625   -3.4292    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -1.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542   -4.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4708   -5.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9917   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875   -5.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0000   -5.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4250   -0.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7167   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2583   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4292   -1.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  1  0
  5  2  2  0
  6  4  1  0
  7 10  1  0
  8  9  1  0
  9  4  2  0
 10  2  1  0
 11  6  2  0
 12 22  1  0
 13  8  2  0
 14  7  1  0
 14 15  1  1
 16  8  1  0
 17 16  1  0
 18 35  1  0
 19 18  3  0
 20 12  1  0
 21  3  2  0
 22 28  2  0
 23 17  1  0
 24 12  2  0
 25 15  2  0
 26 38  2  0
 27 29  2  0
 28 30  1  0
 29 23  1  0
 30 23  2  0
 31 32  1  0
 32 20  1  0
 33  1  1  0
 34 13  1  0
 35 17  1  0
 36  7  1  0
 37 15  1  0
 38 31  1  0
 39 14  1  0
 40 36  1  0
 41 44  2  0
 42 31  2  0
 43 37  1  0
 44 42  1  0
  6  5  1  0
 13 11  1  0
 40 39  1  0
 27 22  1  0
 41 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA333693

   methyl (2S)-1-[[7-chloro-3-methyl-4-oxo-6-[[N-prop-2-ynyl-4-(pyridin-3-ylmethylcarbamoyl)anilino]methyl]quinazolin-2-yl]methyl]pyrrolidine-2-carboxylate

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: 613.12

Molecular Weight (Monoisotopic): 612.2252

AlogP: 3.69

#Rotatable Bonds: 10

Polar Surface Area: 109.66

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.09

CX LogP: 3.38

CX LogD: 3.37

Aromatic Rings: 4

Heavy Atoms: 44

QED Weighted: 0.21

Np Likeness Score: -1.59

References

1. Bavetsias V, Skelton LA, Yafai F, Mitchell F, Wilson SC, Allan B, Jackman AL..  (2002)  The design and synthesis of water-soluble analogues of CB30865, a quinazolin-4-one-based antitumor agent.,  45  (17): [PMID:12166942] [10.1021/jm011081s]

Source

Source(1):

• Scientific Literature