N-(4-(3-bromo-1H-indol-5-ylamino)quinazolin-6-yl)-3-chloropropanamide

ID: ALA5208454

PubChem CID: 153253814

Max Phase: Preclinical

Molecular Formula: C19H15BrClN5O

Molecular Weight: 444.72

Names and Identifiers

Canonical SMILES:  O=C(CCCl)Nc1ccc2ncnc(Nc3ccc4[nH]cc(Br)c4c3)c2c1

Standard InChI:  InChI=1S/C19H15BrClN5O/c20-15-9-22-16-3-2-12(7-13(15)16)26-19-14-8-11(25-18(27)5-6-21)1-4-17(14)23-10-24-19/h1-4,7-10,22H,5-6H2,(H,25,27)(H,23,24,26)

Standard InChI Key:  WTWFBKFNVCFROY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    0.0830   -0.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302   -1.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0857   -2.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7924   -1.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7924   -0.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5073   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2235   -0.8263    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2235   -1.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5103   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5073    0.4140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2206    0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2206    1.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9319    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6496    1.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6496    0.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9383    0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4288    0.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9187    1.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4471    1.8972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6426   -0.2137    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3476   -0.4097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0611   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7745   -0.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4878   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0611   -1.6501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2035   -0.4144    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  6  7  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
  5 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 12 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  1  0
 18 21  1  0
  2 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  2  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5208454

   ---

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: 444.72

Molecular Weight (Monoisotopic): 443.0148

AlogP: 5.18

#Rotatable Bonds: 5

Polar Surface Area: 82.70

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.90

CX Basic pKa: 3.98

CX LogP: 4.34

CX LogD: 4.34

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.37

Np Likeness Score: -1.29

References

1. Tang Q, Peng T, Hu J, Zhang T, Chen P, Chen D, Wang Y, Chen L, Tong L, Chen Y, Xie H, Liang G..  (2022)  Discovery of N-(3-bromo-1H-indol-5-yl)-quinazolin-4-amine as an effective molecular skeleton to develop reversible/irreversible pan-HER inhibitors.,  233  [PMID:35259690] [10.1016/j.ejmech.2022.114249]

Source

Source(1):

• Scientific Literature