4-Amino-5-fluoro-3-(6-(4-methylpiperazin-1-yl)-1H-benzo[d]imidazol-2-yl)quinolin-2(1H)-one

ID: ALA522892

Max Phase: Phase

Molecular Formula: C21H21FN6O

Molecular Weight: 392.44

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Dovitinib | Tki-258 | CHIR-258 | GFKI-258 | NVP-TKI258 | TKI-258

Synonyms from Alternative Forms(5): Dovitinib lactate hydrate | Chir-258 (hydrate) | Dovitinib lactate | Tki258 (hydrate) | CHIR-258

Canonical SMILES:  CN1CCN(c2ccc3nc(-c4c(N)c5c(F)cccc5[nH]c4=O)[nH]c3c2)CC1

Standard InChI:  InChI=1S/C21H21FN6O/c1-27-7-9-28(10-8-27)12-5-6-14-16(11-12)25-20(24-14)18-19(23)17-13(22)3-2-4-15(17)26-21(18)29/h2-6,11H,7-10H2,1H3,(H,24,25)(H3,23,26,29)

Standard InChI Key:  PIQCTGMSNWUMAF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   -1.4042   -0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5792   -0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8167    0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8167   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6417    0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -1.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6417   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958    0.1458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0542   -0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6875   -0.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8333    0.3042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6875   -0.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042    0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -0.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2625    1.1292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0542    0.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4042   -1.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4042    0.9083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5458   -0.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8333    1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042   -1.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -0.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5458    1.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2625    0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6417    1.6208    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8792   -0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9750    1.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2917    0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8792    0.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  1  1  0
  5  3  1  0
  6  2  2  0
  7  4  1  0
  8  2  1  0
  9  5  2  0
 10  8  1  0
 11 14  1  0
 12  6  1  0
 13 10  2  0
 14 13  1  0
 15 23  1  0
 16  5  1  0
 17  4  2  0
 18  3  1  0
 19 11  1  0
 20 11  1  0
 21 12  2  0
 22 21  1  0
 23 20  1  0
 24 19  1  0
 25 16  1  0
 26  9  1  0
 27 15  1  0
 28 29  1  0
 29 16  2  0
 10 12  1  0
  7  9  1  0
 22 14  2  0
 28 26  2  0
 24 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA522892

   DOVITINIB

2. Alternative Forms:

   

   ALA522892

   Dovitinib (TKI258) Lactate

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 392.44

Molecular Weight (Monoisotopic): 392.1761

AlogP: 2.54

#Rotatable Bonds: 2

Polar Surface Area: 94.04

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.56

CX Basic pKa: 7.87

CX LogP: 1.35

CX LogD: 1.04

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: -1.30

References

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Source

Source(9):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• AstraZeneca Deposited Data
• Patent Bioactivity Data
• Kuster lab chemical proteomics drug profiling
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6
• EU-OPENSCREEN dataset