(3-((2-(3,5-dimorpholinophenylamino)pyrimidin-4-yl)(methyl)amino)-4-methylphenyl)methanol

ID: ALA1762530

PubChem CID: 24894017

Max Phase: Preclinical

Molecular Formula: C27H34N6O3

Molecular Weight: 490.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(CO)cc1N(C)c1ccnc(Nc2cc(N3CCOCC3)cc(N3CCOCC3)c2)n1

Standard InChI:  InChI=1S/C27H34N6O3/c1-20-3-4-21(19-34)15-25(20)31(2)26-5-6-28-27(30-26)29-22-16-23(32-7-11-35-12-8-32)18-24(17-22)33-9-13-36-14-10-33/h3-6,15-18,34H,7-14,19H2,1-2H3,(H,28,29,30)

Standard InChI Key:  BUHNODQEWUMKMH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   18.4838  -14.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1983  -14.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9146  -14.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9118  -13.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.6295  -14.5090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1940  -12.0337    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9091  -11.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.4789  -11.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7692  -14.5101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0527  -14.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3403  -14.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3354  -15.3277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   22.7679  -14.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7670  -13.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0470  -12.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3369  -13.2729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0428  -12.0329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7550  -11.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1798  -10.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7497  -10.7962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4568  -10.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1836  -11.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4742  -12.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3265  -11.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4786  -12.8491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4490   -9.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1594   -9.1379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 14 19  1  0
 15 16  1  0
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  7 20  1  0
  2  3  1  0
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  5  6  2  0
 21 22  1  0
  6  1  1  0
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  8 13  1  0
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  9 10  1  0
 24 25  2  0
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 10 11  1  0
 24 26  1  0
 11 12  1  0
 26 27  1  0
 27 32  2  0
 12 13  1  0
 31 28  2  0
 28 30  1  0
 29 27  1  0
 29 30  2  0
  1  2  2  0
  2 14  1  0
 31 32  1  0
 14 15  1  0
  4  7  1  0
  3  4  2  0
 26 33  1  0
  6  8  1  0
 32 34  1  0
  8  9  1  0
 30 35  1  0
 35 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1762530

   (3-((2-(3,5-Dimorpholinophenylamino)pyrimidin-4-yl)(methyl)amino)-4-methylphenyl)methanol

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: 490.61

Molecular Weight (Monoisotopic): 490.2692

AlogP: 3.46

#Rotatable Bonds: 7

Polar Surface Area: 86.22

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.66

CX Basic pKa: 4.53

CX LogP: 3.95

CX LogD: 3.95

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.52

Np Likeness Score: -1.06

References

1. Barlaam B, Ducray R, Lambert-van der Brempt C, Plé P, Bardelle C, Brooks N, Coleman T, Cross D, Kettle JG, Read J..  (2011)  Inhibitors of the tyrosine kinase EphB4. Part 4: Discovery and optimization of a benzylic alcohol series.,  21  (8): [PMID:21441027] [10.1016/j.bmcl.2011.03.009]

2. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

Source

Source(2):

• Scientific Literature
• AstraZeneca Deposited Data