4-((2-Phenylquinazolin-4-yl)amino)benzoic Acid

ID: ALA1624741

PubChem CID: 715632

Max Phase: Preclinical

Molecular Formula: C21H15N3O2

Molecular Weight: 341.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(Nc2nc(-c3ccccc3)nc3ccccc23)cc1

Standard InChI:  InChI=1S/C21H15N3O2/c25-21(26)15-10-12-16(13-11-15)22-20-17-8-4-5-9-18(17)23-19(24-20)14-6-2-1-3-7-14/h1-13H,(H,25,26)(H,22,23,24)

Standard InChI Key:  URQSXBUBPRZCPZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    7.8372   -3.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5517   -2.1418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2648    0.3332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9793    1.5707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9793   -0.9043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6938    0.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9793   -0.0793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6938    1.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2648    1.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5504    1.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4083   -0.0793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6938   -1.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4083    1.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1227    0.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1227    1.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359    1.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5504    2.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4083   -0.9043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6938   -2.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1227   -2.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1227   -1.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4083   -2.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214    1.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359    2.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8372   -2.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214    2.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 25  2  0
  2 25  1  0
  3  7  2  0
  3  9  1  0
  4  8  1  0
  4  9  2  0
  5  7  1  0
  5 12  1  0
  6  7  1  0
  6  8  1  0
  6 11  2  0
  8 13  2  0
  9 10  1  0
 10 16  2  0
 10 17  1  0
 11 14  1  0
 12 18  2  0
 12 19  1  0
 13 15  1  0
 14 15  2  0
 16 23  1  0
 17 24  2  0
 18 21  1  0
 19 22  2  0
 20 21  2  0
 20 22  1  0
 20 25  1  0
 23 26  2  0
 24 26  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA1624741

   4-[(2-Phenylquinazolin-4-yl)amino]benzoic acid

2. Parent:

   

   ALA1624741

   CID 715632

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: 341.37

Molecular Weight (Monoisotopic): 341.1164

AlogP: 4.74

#Rotatable Bonds: 4

Polar Surface Area: 75.11

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.75

CX Basic pKa: 4.04

CX LogP: 4.80

CX LogD: 2.56

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.56

Np Likeness Score: -1.20

References

1. Krapf MK, Wiese M..  (2016)  Synthesis and Biological Evaluation of 4-Anilino-quinazolines and -quinolines as Inhibitors of Breast Cancer Resistance Protein (ABCG2).,  59  (11): [PMID:27148793] [10.1021/acs.jmedchem.6b00330]

Source

Source(1):

• Scientific Literature