7-((1s,3s)-3-(azetidin-1-ylmethyl)cyclobutyl)-5-(3-(((R)-tetrahydro-2H-pyran-2-yl)methoxy)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

ID: ALA3786383

PubChem CID: 67035535

Max Phase: Preclinical

Molecular Formula: C26H33N5O2

Molecular Weight: 447.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(-c1cccc(OC[C@H]3CCCCO3)c1)cn2[C@H]1C[C@@H](CN2CCC2)C1

Standard InChI:  InChI=1S/C26H33N5O2/c27-25-24-23(19-5-3-7-21(13-19)33-16-22-6-1-2-10-32-22)15-31(26(24)29-17-28-25)20-11-18(12-20)14-30-8-4-9-30/h3,5,7,13,15,17-18,20,22H,1-2,4,6,8-12,14,16H2,(H2,27,28,29)/t18-,20+,22-/m1/s1

Standard InChI Key:  UTHVKVUADCCITP-KAGYGMCKSA-N

Molfile:  

     RDKit          2D

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   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749    2.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2965    5.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2218    4.2301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6621    2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9991    2.7132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1852   -2.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3864   -3.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187   -6.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4587   -6.5134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1303   -7.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4455   -7.0930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7243   -5.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8879    6.3826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4499    7.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5265    8.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0862   10.3491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1608   11.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3242   11.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840    9.9269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9586    8.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  6  7  1  0
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  9 10  1  0
  4 16  1  0
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 18 19  1  0
 19 20  1  0
 20 17  1  0
 17  7  1  6
 19 21  1  6
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 22  1  0
 12 26  1  0
 26 27  1  0
 28 27  1  1
 28 29  1  0
 28 33  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3786383

   7-[3-(Azetidin-1-Ylmethyl)cyclobutyl]-5-[3-[[(2~{r})-Oxan-2-Yl]methoxy]phenyl]pyrrolo[2,3-D]pyrimidin-4-Amine

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: 447.58

Molecular Weight (Monoisotopic): 447.2634

AlogP: 4.29

#Rotatable Bonds: 7

Polar Surface Area: 78.43

Molecular Species: BASE

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.31

CX LogP: 3.29

CX LogD: 1.36

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.58

Np Likeness Score: -0.58

References

1. Stauffer F, Cowan-Jacob SW, Scheufler C, Furet P..  (2016)  Identification of a 5-[3-phenyl-(2-cyclic-ether)-methylether]-4-aminopyrrolo[2,3-d]pyrimidine series of IGF-1R inhibitors.,  26  (8): [PMID:26951750] [10.1016/j.bmcl.2016.02.074]

2. Fairhurst RA, Marsilje TH, Stutz S, Boos A, Niklaus M, Chen B, Jiang S, Lu W, Furet P, McCarthy C, Stauffer F, Guagnano V, Vaupel A, Michellys PY, Schnell C, Jeay S..  (2016)  Optimisation of a 5-[3-phenyl-(2-cyclic-ether)-methyl-ether]-4-aminopyrrolopyrimidine series of IGF-1R inhibitors.,  26  (8): [PMID:26951753] [10.1016/j.bmcl.2016.02.075]

Source

Source(1):

• Scientific Literature