methyl (S)-2-(4-((2-amino-6-methyl-4-oxo-3,4-dihydroquinazolin-5-yl)thio)benzamido)-3-(4-aminophenyl)propanoate

ID: ALA5282201

Max Phase: Preclinical

Molecular Formula: C26H25N5O4S

Molecular Weight: 503.58

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](Cc1ccc(N)cc1)NC(=O)c1ccc(Sc2c(C)ccc3nc(N)[nH]c(=O)c23)cc1

Standard InChI:  InChI=1S/C26H25N5O4S/c1-14-3-12-19-21(24(33)31-26(28)30-19)22(14)36-18-10-6-16(7-11-18)23(32)29-20(25(34)35-2)13-15-4-8-17(27)9-5-15/h3-12,20H,13,27H2,1-2H3,(H,29,32)(H3,28,30,31,33)/t20-/m0/s1

Standard InChI Key:  CPLFCKMJIWXSGH-FQEVSTJZSA-N

Molfile:  

 
     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
    3.2052   -1.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2052   -1.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9168   -0.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6257   -1.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6257   -1.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9186   -2.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3371   -2.2685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4938   -0.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7823   -1.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7823   -1.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5068   -2.2761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0621   -2.2515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0621   -3.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0709   -0.6256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3594   -1.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3594   -1.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3519   -0.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0590   -1.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7724   -0.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7724    0.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4838    0.6064    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4838    1.4278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1970    1.8341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1970    2.6589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9144    3.0728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6257    2.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6257    1.8357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9093    1.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9093    0.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3371    3.0671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4856    3.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769    2.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769    1.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0655    1.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0608    0.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3519    0.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  3  1  0
  5  4  2  0
  6  5  1  0
  1  6  2  0
  5  7  1  0
  8  2  1  0
  9  8  1  0
  9 10  1  1
 10 11  2  0
 10 12  1  0
 12 13  1  0
 14  9  1  0
 15 14  1  0
 15 16  2  0
 17 15  1  0
 18 17  1  0
 19 18  2  0
 20 19  1  0
 21 20  1  0
 22 21  1  0
 23 22  2  0
 24 23  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 23 28  1  0
 28 29  2  0
 26 30  1  0
 31 24  2  0
 32 31  1  0
 33 32  2  0
 22 33  1  0
 33 34  1  0
 35 20  2  0
 36 35  1  0
 17 36  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5282201

   ---

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: 503.58

Molecular Weight (Monoisotopic): 503.1627

AlogP: 3.06

#Rotatable Bonds: 7

Polar Surface Area: 153.19

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.23

CX Basic pKa: 4.23

CX LogP: 3.29

CX LogD: 3.29

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.22

Np Likeness Score: -0.55

References

1. Alagarsamy V, Chitra K, Saravanan G, Solomon VR, Sulthana MT, Narendhar B..  (2018)  An overview of quinazolines: Pharmacological significance and recent developments.,  151  [PMID:29656203] [10.1016/j.ejmech.2018.03.076]

Source

Source(1):

• Scientific Literature