1-[4-[3-chloro-4-[(3-fluorophenyl)methoxy]anilino]-8,9-dihydro-7H-pyrimido[5,4-h][1,5]benzoxazepin-6-yl]-4-(1-piperidyl)but-2-en-1-one

ID: ALA4638194

PubChem CID: 78322917

Max Phase: Preclinical

Molecular Formula: C33H33ClFN5O3

Molecular Weight: 602.11

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(/C=C/CN1CCCCC1)N1CCCOc2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3cc21

Standard InChI:  InChI=1S/C33H33ClFN5O3/c34-27-18-25(10-11-30(27)43-21-23-7-4-8-24(35)17-23)38-33-26-19-29-31(20-28(26)36-22-37-33)42-16-6-15-40(29)32(41)9-5-14-39-12-2-1-3-13-39/h4-5,7-11,17-20,22H,1-3,6,12-16,21H2,(H,36,37,38)/b9-5+

Standard InChI Key:  GNLUBKWNERBEDJ-WEVVVXLNSA-N

Molfile:  

 
     RDKit          2D

 43 48  0  0  0  0  0  0  0  0999 V2000
    8.3907  -15.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3898  -14.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0988  -14.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0980  -15.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8091  -15.8544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5216  -15.4453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5184  -14.6199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8066  -14.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8038  -13.3902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5143  -12.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2268  -13.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9367  -12.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9344  -12.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2162  -11.7480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5091  -12.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6498  -13.3869    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.6443  -11.7421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3580  -12.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0638  -11.7353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7746  -12.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4840  -11.7334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4805  -10.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7618  -10.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0553  -10.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1975  -12.1431    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.6898  -14.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6865  -15.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0410  -15.9605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0454  -14.1114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2390  -15.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2413  -14.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8853  -15.0380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0411  -13.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7466  -12.8814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3312  -12.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6257  -13.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9158  -12.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2103  -13.3089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5034  -12.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7999  -13.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8001  -14.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5098  -14.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2194  -14.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 27  1  1  0
  1  4  2  0
  3  2  2  0
  2 26  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 12 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 21 25  1  0
 26 27  2  0
 27 28  1  0
 26 29  1  0
 28 30  1  0
 29 31  1  0
 30 32  1  0
 31 32  1  0
 29 33  1  0
 33 34  2  0
 33 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 38 43  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4638194

   (E)-1-[4-[3-chloro-4-[(3-fluorophenyl)methoxy]anilino]-8,9-dihydro-7H-pyrimido[5,4-h][1,5]benzoxazepin-6-yl]-4-piperidin-1-ylbut-2-en-1-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 602.11

Molecular Weight (Monoisotopic): 601.2256

AlogP: 6.90

#Rotatable Bonds: 8

Polar Surface Area: 79.82

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 8.42

CX LogP: 6.03

CX LogD: 4.97

Aromatic Rings: 4

Heavy Atoms: 43

QED Weighted: 0.22

Np Likeness Score: -1.41

References

1. Sun M, Jia J, Sun H, Wang F..  (2020)  Design and synthesis of a novel class EGFR/HER2 dual inhibitors containing tricyclic oxazine fused quinazolines scaffold.,  30  (9): [PMID:32139324] [10.1016/j.bmcl.2020.127045]

Source

Source(1):

• Scientific Literature