1,4:3,6-dianhydro-2-O-[4-[(3,4-dichloro-2-fluorophenyl)amino]-6-(methyloxy)quinazolin-7-y1]-5-O-methyl-L-iditol

ID: ALA3986404

PubChem CID: 134156210

Max Phase: Preclinical

Molecular Formula: C22H20Cl2FN3O5

Molecular Weight: 496.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(Nc3ccc(Cl)c(Cl)c3F)ncnc2cc1O[C@@H]1C[C@H]2OC[C@H](OC)[C@H]2O1

Standard InChI:  InChI=1S/C22H20Cl2FN3O5/c1-29-14-5-10-13(6-15(14)32-18-7-16-21(33-18)17(30-2)8-31-16)26-9-27-22(10)28-12-4-3-11(23)19(24)20(12)25/h3-6,9,16-18,21H,7-8H2,1-2H3,(H,26,27,28)/t16-,17+,18+,21+/m1/s1

Standard InChI Key:  CMDXLFALYMWXLO-WKRCXCSHSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
    3.9194   -4.2465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7355   -4.2039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1761   -4.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9140   -3.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1002   -3.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3634   -4.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9907   -4.8472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4340   -5.5316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2500   -5.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6206   -4.7578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1751   -4.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5445   -3.3476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3605   -3.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8056   -3.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6208   -3.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9911   -3.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5401   -2.5281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7264   -2.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6519   -2.7946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0194   -2.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5483   -4.9745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7401   -5.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9180   -5.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3402   -6.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6114   -5.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0334   -6.4895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4050   -7.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2126   -7.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8985   -5.5016    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0447   -6.6902    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4353   -4.7166    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7907   -7.6672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5795   -8.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8070   -3.1690    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.0670   -4.6287    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  7  1  0
  6  4  1  0
  4  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11  6  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  5 19  1  0
 19 20  1  0
 21  1  1  1
 21 22  1  0
 22 25  1  0
 24 23  1  0
 23 21  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 24  1  0
 25 29  1  1
 24 30  1  1
 14 31  1  0
 28 32  1  1
 32 33  1  0
 16 34  1  0
 15 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3986404

   ---

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: 496.32

Molecular Weight (Monoisotopic): 495.0764

AlogP: 4.74

#Rotatable Bonds: 6

Polar Surface Area: 83.96

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.99

CX Basic pKa: 4.32

CX LogP: 4.79

CX LogD: 4.79

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.49

Np Likeness Score: -0.19

References

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

Source

Source(1):

• Patent Bioactivity Data