(R)-2-((trans-4-(4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexyl)amino)propanoic acid

ID: ALA4212500

Max Phase: Preclinical

Molecular Formula: C27H29N5O3

Molecular Weight: 471.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](N[C@H]1CC[C@H](n2cc(-c3ccc(Oc4ccccc4)cc3)c3c(N)ncnc32)CC1)C(=O)O

Standard InChI:  InChI=1S/C27H29N5O3/c1-17(27(33)34)31-19-9-11-20(12-10-19)32-15-23(24-25(28)29-16-30-26(24)32)18-7-13-22(14-8-18)35-21-5-3-2-4-6-21/h2-8,13-17,19-20,31H,9-12H2,1H3,(H,33,34)(H2,28,29,30)/t17-,19-,20-/m1/s1

Standard InChI Key:  POLFXOSYBGYACO-MISYRCLQSA-N

Molfile:  

     RDKit          2D

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   10.0491   -9.7520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0480  -10.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7589  -10.9899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7571   -9.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4729   -9.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4777  -10.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2651  -10.8241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7486  -10.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.5106   -8.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3181   -8.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5673   -7.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0101   -7.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2008   -7.3152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9554   -8.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2582   -6.3499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   14.3100   -5.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7547   -8.5126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5274  -11.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9753  -12.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2305  -13.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0378  -13.1703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5896  -12.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3341  -11.7670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2931  -13.9502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0963  -14.1189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6439  -13.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4470  -13.6765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3885  -12.7280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3516  -14.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
  4 23  1  0
 24  7  1  1
 24 25  1  0
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 27 30  1  6
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 31 35  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4212500

   ---

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: 471.56

Molecular Weight (Monoisotopic): 471.2270

AlogP: 5.02

#Rotatable Bonds: 7

Polar Surface Area: 115.29

Molecular Species: ZWITTERION

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.19

CX Basic pKa: 10.83

CX LogP: 1.95

CX LogD: 1.77

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.35

Np Likeness Score: -0.41

References

1. Koda Y, Kikuzato K, Mikuni J, Tanaka A, Yuki H, Honma T, Tomabechi Y, Kukimoto-Niino M, Shirouzu M, Shirai F, Koyama H..  (2017)  Identification of pyrrolo[2,3-d]pyrimidines as potent HCK and FLT3-ITD dual inhibitors.,  27  (22): [PMID:29037944] [10.1016/j.bmcl.2017.10.012]

Source

Source(1):

• Scientific Literature