(R)-1-(cis-4-(4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexyl)pyrrolidine-2-carboxylic acid

ID: ALA4216680

Max Phase: Preclinical

Molecular Formula: C29H31N5O3

Molecular Weight: 497.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(-c1ccc(Oc3ccccc3)cc1)cn2[C@H]1CC[C@@H](N2CCC[C@@H]2C(=O)O)CC1

Standard InChI:  InChI=1S/C29H31N5O3/c30-27-26-24(19-8-14-23(15-9-19)37-22-5-2-1-3-6-22)17-34(28(26)32-18-31-27)21-12-10-20(11-13-21)33-16-4-7-25(33)29(35)36/h1-3,5-6,8-9,14-15,17-18,20-21,25H,4,7,10-13,16H2,(H,35,36)(H2,30,31,32)/t20-,21+,25-/m1/s1

Standard InChI Key:  DORRCVAXQFZOLU-TYBLODHISA-N

Molfile:  

     RDKit          2D

 37 42  0  0  0  0  0  0  0  0999 V2000
   10.0533   -9.7562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0522  -10.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7635  -10.9946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7617   -9.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4778   -9.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4826  -10.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2703  -10.8287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7540  -10.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2626   -9.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5159   -8.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3238   -8.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5730   -7.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0156   -7.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2059   -7.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9605   -8.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2638   -6.3526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0697   -6.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6236   -6.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4289   -6.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6777   -5.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1191   -5.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3160   -5.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7593   -8.5162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5327  -11.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9804  -12.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2357  -13.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0433  -13.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5953  -12.5590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3397  -11.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2988  -13.9561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8223  -14.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3064  -15.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0867  -15.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0846  -14.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7474  -13.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4984  -14.0565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6594  -12.9084    0.0000 O   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  1
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 30  1  0
 34 35  1  1
 35 36  1  0
 35 37  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4216680

   ---

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: 497.60

Molecular Weight (Monoisotopic): 497.2427

AlogP: 5.51

#Rotatable Bonds: 6

Polar Surface Area: 106.50

Molecular Species: ZWITTERION

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.89

CX Basic pKa: 11.08

CX LogP: 2.13

CX LogD: 1.94

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.36

Np Likeness Score: -0.35

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