(3S,8aS)-3-({[4-[(4-bromo-3-chloro-2-fluorophenyl)amino]-6-(methyloxy)quinazolin-7-yl]oxy}methyl)hexahydropyrrolo[1,2-a]pyrazin-1(2H)-one

ID: ALA3986135

PubChem CID: 57802807

Max Phase: Preclinical

Molecular Formula: C23H22BrClFN5O3

Molecular Weight: 550.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(Nc3ccc(Br)c(Cl)c3F)ncnc2cc1OC[C@@H]1CN2CCC[C@H]2C(=O)N1

Standard InChI:  InChI=1S/C23H22BrClFN5O3/c1-33-18-7-13-16(27-11-28-22(13)30-15-5-4-14(24)20(25)21(15)26)8-19(18)34-10-12-9-31-6-2-3-17(31)23(32)29-12/h4-5,7-8,11-12,17H,2-3,6,9-10H2,1H3,(H,29,32)(H,27,28,30)/t12-,17-/m0/s1

Standard InChI Key:  OEGXYNWEJSFYPO-SJCJKPOMSA-N

Molfile:  

     RDKit          2D

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   19.3191   -9.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3162   -9.0639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6076   -8.6586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6094  -10.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9014   -9.8870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1953  -10.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1960  -11.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9087  -11.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6119  -11.1092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0274  -10.2940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7345   -9.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4395  -10.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1461   -9.8832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1452   -9.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.0179   -8.6652    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.4278   -7.8407    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.8518   -8.6545    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   17.9128  -12.3373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6225  -12.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4894  -11.5236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4917  -12.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7851  -12.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0801  -12.3414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3757  -12.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7930  -13.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6671  -12.3414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0777  -13.9773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3789  -13.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7715  -14.1030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0948  -14.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9021  -14.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6653  -13.1535    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0
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  9 21  1  0
 21 22  1  0
  8 23  1  0
 23 24  1  0
 25 24  1  6
 25 26  1  0
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 27 31  1  0
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 27 29  2  0
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 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 30  1  0
 31 35  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3986135

   US9796704, Entry 53

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: 550.82

Molecular Weight (Monoisotopic): 549.0579

AlogP: 4.28

#Rotatable Bonds: 6

Polar Surface Area: 88.61

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.64

CX Basic pKa: 7.60

CX LogP: 4.08

CX LogD: 3.66

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.44

Np Likeness Score: -0.48

References

1.  (2009)  Receptor-type kinase modulators and methods of use, 

Source

Source(1):

• Patent Bioactivity Data