1-(4-bromophenyl)-3-(3-((1-phenethyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)methyl)phenyl)urea

ID: ALA3128236

PubChem CID: 76314769

Max Phase: Preclinical

Molecular Formula: C27H24BrN7O

Molecular Weight: 542.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(Br)cc1)Nc1cccc(CNc2ncnc3c2cnn3CCc2ccccc2)c1

Standard InChI:  InChI=1S/C27H24BrN7O/c28-21-9-11-22(12-10-21)33-27(36)34-23-8-4-7-20(15-23)16-29-25-24-17-32-35(26(24)31-18-30-25)14-13-19-5-2-1-3-6-19/h1-12,15,17-18H,13-14,16H2,(H,29,30,31)(H2,33,34,36)

Standard InChI Key:  ZLIDREACDLOGNW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   22.3670  -14.1092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0751  -14.5181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7847  -14.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7819  -13.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0733  -12.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0749  -15.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3671  -15.7438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3669  -16.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6582  -16.9651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6577  -17.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3658  -18.1911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0730  -16.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0785  -17.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8590  -18.0300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3360  -17.3642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8501  -16.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1166  -18.8055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9171  -18.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1747  -19.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6308  -20.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8879  -21.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6891  -21.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2327  -20.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9728  -19.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4881  -12.8748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1973  -13.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9035  -12.8694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2004  -14.0979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6127  -13.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6127  -14.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3211  -14.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0282  -14.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0225  -13.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3135  -12.8624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7379  -14.4912    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 14  1  0
 13  9  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 13  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
  5 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
 33 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3128236

   1-(4-Bromophenyl)-3-[3-[[[1-(2-phenylethyl)pyrazolo[3,4-d]pyrimidin-4-yl]amino]methyl]phenyl]urea

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: 542.44

Molecular Weight (Monoisotopic): 541.1226

AlogP: 6.09

#Rotatable Bonds: 8

Polar Surface Area: 96.76

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.49

CX Basic pKa: 3.62

CX LogP: 5.58

CX LogD: 5.58

Aromatic Rings: 5

Heavy Atoms: 36

QED Weighted: 0.22

Np Likeness Score: -1.75

References

1. Sartini S, Coviello V, Bruno A, La Pietra V, Marinelli L, Simorini F, Taliani S, Salerno S, Marini AM, Fioravanti A, Orlandi P, Antonelli A, Da Settimo F, Novellino E, Bocci G, La Motta C..  (2014)  Structure-based optimization of tyrosine kinase inhibitor CLM3. Design, synthesis, functional evaluation, and molecular modeling studies.,  57  (4): [PMID:24447248] [10.1021/jm401358b]

Source

Source(1):

• Scientific Literature