(R)-N1, N1-Dimethyl-N2-(4-(4-((1-phenylethyl)amino)furo[2,3-d]pyrimidin-6-yl)phenyl)ethane-1,2-diamine

ID: ALA3901622

PubChem CID: 134134898

Max Phase: Preclinical

Molecular Formula: C24H27N5O

Molecular Weight: 401.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](Nc1ncnc2oc(-c3ccc(NCCN(C)C)cc3)cc12)c1ccccc1

Standard InChI:  InChI=1S/C24H27N5O/c1-17(18-7-5-4-6-8-18)28-23-21-15-22(30-24(21)27-16-26-23)19-9-11-20(12-10-19)25-13-14-29(2)3/h4-12,15-17,25H,13-14H2,1-3H3,(H,26,27,28)/t17-/m1/s1

Standard InChI Key:  QJXSNAGEGZAXGL-QGZVFWFLSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   28.3980  -16.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3969  -17.1097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1049  -17.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1032  -15.8813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8118  -16.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8120  -17.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5950  -17.3639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0787  -16.6977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5946  -16.0320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1052  -18.3358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8130  -18.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8132  -19.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5206  -18.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1043  -19.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1042  -20.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8126  -21.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5225  -20.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5191  -19.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8927  -16.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3009  -17.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1173  -17.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5265  -16.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1133  -15.9870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2982  -15.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3437  -16.6955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.7535  -17.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5707  -17.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9804  -18.1082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.7976  -18.1068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5730  -18.8166    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  2  0
  8  9  1  0
  9  5  1  0
  3 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  6
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 12  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  8 19  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3901622

   ---

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: 401.51

Molecular Weight (Monoisotopic): 401.2216

AlogP: 5.04

#Rotatable Bonds: 8

Polar Surface Area: 66.22

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.91

CX LogP: 3.84

CX LogD: 2.33

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.43

Np Likeness Score: -1.02

References

1. Han J, Kaspersen SJ, Nervik S, Nørsett KG, Sundby E, Hoff BH..  (2016)  Chiral 6-aryl-furo[2,3-d]pyrimidin-4-amines as EGFR inhibitors.,  119  [PMID:27235841] [10.1016/j.ejmech.2016.04.054]

Source

Source(1):

• Scientific Literature