1-(4-(4-Amino-7-benzyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-phenyl)-3-(5-(tert-butyl)isoxazol-3-yl)urea

ID: ALA4551816

PubChem CID: 155555805

Max Phase: Preclinical

Molecular Formula: C27H27N7O2

Molecular Weight: 481.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cc(NC(=O)Nc2ccc(-c3cn(Cc4ccccc4)c4ncnc(N)c34)cc2)no1

Standard InChI:  InChI=1S/C27H27N7O2/c1-27(2,3)21-13-22(33-36-21)32-26(35)31-19-11-9-18(10-12-19)20-15-34(14-17-7-5-4-6-8-17)25-23(20)24(28)29-16-30-25/h4-13,15-16H,14H2,1-3H3,(H2,28,29,30)(H2,31,32,33,35)

Standard InChI Key:  VXPZMKHJUJLFES-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   32.4213   -4.2039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4172   -5.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1310   -3.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1230   -4.6089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5804   -5.7286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5792   -6.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   25.2855   -5.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   26.7789   -6.7920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2563   -6.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7712   -5.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2830   -4.5025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.1917   -7.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.1913   -3.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7812   -4.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4257   -2.6538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2429   -2.6588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6559   -1.9537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6471   -3.3690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.4643   -3.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9369   -4.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7207   -2.9745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9451   -2.7173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0089   -7.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4178   -8.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2342   -8.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6394   -7.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2222   -6.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4072   -6.7847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
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  9 15  1  0
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 17 18  2  0
 18 19  1  0
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 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28  1  2  0
  1 29  1  0
 29 30  1  0
 30 27  2  0
 16 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4551816

   ---

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: 481.56

Molecular Weight (Monoisotopic): 481.2226

AlogP: 5.66

#Rotatable Bonds: 5

Polar Surface Area: 123.89

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.27

CX Basic pKa: 6.13

CX LogP: 5.45

CX LogD: 5.37

Aromatic Rings: 5

Heavy Atoms: 36

QED Weighted: 0.30

Np Likeness Score: -1.35

References

1. Yuan X, Chen Y, Zhang W, He J, Lei L, Tang M, Liu J, Li M, Dou C, Yang T, Yang L, Yang S, Wei Y, Peng A, Niu T, Xiang M, Ye H, Chen L..  (2019)  Identification of Pyrrolo[2,3- d]pyrimidine-Based Derivatives as Potent and Orally Effective Fms-like Tyrosine Receptor Kinase 3 (FLT3) Inhibitors for Treating Acute Myelogenous Leukemia.,  62  (8): [PMID:30939008] [10.1021/acs.jmedchem.9b00223]

Source

Source(1):

• Scientific Literature