1-(2-((5-Chloro-2-((2-methoxy-4-(4-(4-methylpiperazin-1-yl)-piperidin-1-yl)phenyl)amino)pyrimidin-4-yl)amino)phenyl)ethan-1-ol

ID: ALA3822499

PubChem CID: 127049464

Max Phase: Preclinical

Molecular Formula: C29H38ClN7O2

Molecular Weight: 552.12

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(N2CCC(N3CCN(C)CC3)CC2)ccc1Nc1ncc(Cl)c(Nc2ccccc2C(C)O)n1

Standard InChI:  InChI=1S/C29H38ClN7O2/c1-20(38)23-6-4-5-7-25(23)32-28-24(30)19-31-29(34-28)33-26-9-8-22(18-27(26)39-3)36-12-10-21(11-13-36)37-16-14-35(2)15-17-37/h4-9,18-21,38H,10-17H2,1-3H3,(H2,31,32,33,34)

Standard InChI Key:  HHXONKYVQVDMAS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    3.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039    3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092    5.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6108    5.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8915   -3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2935   -3.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8748   -8.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5644  -10.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2692   -9.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2767   -8.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5568  -12.0055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8509  -12.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8409  -14.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5370  -15.0056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2429  -14.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2529  -12.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5290  -16.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1954   -3.0153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2317   -3.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0136    6.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0195    7.2070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0288    5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  2  0
  1  7  1  0
  3  8  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  9 14  2  0
  8  9  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 21 26  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 27 32  1  0
 30 33  1  0
 24 27  1  0
 18 21  1  0
 34 35  1  0
 16 34  1  0
  7 15  1  0
  4 36  1  0
 10 37  1  0
 37 38  1  0
 37 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3822499

   ---

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: 552.12

Molecular Weight (Monoisotopic): 551.2776

AlogP: 4.90

#Rotatable Bonds: 8

Polar Surface Area: 89.02

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.58

CX Basic pKa: 8.48

CX LogP: 4.28

CX LogD: 3.11

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.36

Np Likeness Score: -1.23

References

1. Huang WS, Liu S, Zou D, Thomas M, Wang Y, Zhou T, Romero J, Kohlmann A, Li F, Qi J, Cai L, Dwight TA, Xu Y, Xu R, Dodd R, Toms A, Parillon L, Lu X, Anjum R, Zhang S, Wang F, Keats J, Wardwell SD, Ning Y, Xu Q, Moran LE, Mohemmad QK, Jang HG, Clackson T, Narasimhan NI, Rivera VM, Zhu X, Dalgarno D, Shakespeare WC..  (2016)  Discovery of Brigatinib (AP26113), a Phosphine Oxide-Containing, Potent, Orally Active Inhibitor of Anaplastic Lymphoma Kinase.,  59  (10): [PMID:27144831] [10.1021/acs.jmedchem.6b00306]

Source

Source(1):

• Scientific Literature