GNF-Pf-5058

ID: ALA601180

PubChem CID: 15989993

Max Phase: Preclinical

Molecular Formula: C19H20N4O4

Molecular Weight: 368.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: GNF-Pf-5058 | GNF-Pf-5058|MLS001199677|SMR000560127|ethyl 4-[(4-amino-6,7-dimethoxyquinazolin-2-yl)amino]benzoate|CHEMBL601180|BDBM79635|cid_15989993|HMS1821K02|HMS2880O11|AKOS000113808|NCGC00107259-01|C301-4527|ethyl 4-[(4-azanyl-6,7-dimethoxy-quinazolin-2-yl)amino]benzoate|4-[(4-amino-6,7-dimethoxy-2-quinazolinyl)amino]benzoic acid ethyl ester|4-[(4-amino-6,7-dimethoxy-quinazolin-2-yl)amino]benzoic acid ethyl ester

Canonical SMILES:  CCOC(=O)c1ccc(Nc2nc(N)c3cc(OC)c(OC)cc3n2)cc1

Standard InChI:  InChI=1S/C19H20N4O4/c1-4-27-18(24)11-5-7-12(8-6-11)21-19-22-14-10-16(26-3)15(25-2)9-13(14)17(20)23-19/h5-10H,4H2,1-3H3,(H3,20,21,22,23)

Standard InChI Key:  YGNWIQTXRCJLGP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -1.5330   10.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5752    9.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5838    8.2475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8873    7.5036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9233    8.1092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8958    6.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1976    5.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2030    3.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9067    3.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9091    1.5019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2928   -2.6973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911   -1.5017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894   -2.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911    1.5017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894    2.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6050    3.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5995    5.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 23 24  1  0
 24 15  1  0
 24 25  2  0
 25 11  1  0
  9 26  1  0
 26 27  2  0
 27  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA601180

   Ethyl 4-[(4-amino-6,7-dimethoxyquinazolin-2-yl)amino]benzoate

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: 368.39

Molecular Weight (Monoisotopic): 368.1485

AlogP: 3.15

#Rotatable Bonds: 6

Polar Surface Area: 108.59

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.96

CX Basic pKa: 5.52

CX LogP: 3.35

CX LogD: 3.35

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: -0.85

References

1. Plouffe D, Brinker A, McNamara C, Henson K, Kato N, Kuhen K, Nagle A, Adrián F, Matzen JT, Anderson P, Nam TG, Gray NS, Chatterjee A, Janes J, Yan SF, Trager R, Caldwell JS, Schultz PG, Zhou Y, Winzeler EA..  (2008)  In silico activity profiling reveals the mechanism of action of antimalarials discovered in a high-throughput screen.,  105  (26): [PMID:18579783] [10.1073/pnas.0802982105]

2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

Source

Source(2):

• Novartis Malaria Screening
• PubChem BioAssays