N-(4-(6-(1-acryloylpiperidin-3-ylamino)-9H-purin-2-ylamino)phenyl)-N-methylpropionamide

ID: ALA1643959

PubChem CID: 49821040

Max Phase: Preclinical

Molecular Formula: C23H28N8O2

Molecular Weight: 448.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)N1CCCC(Nc2nc(Nc3ccc(N(C)C(=O)CC)cc3)nc3[nH]cnc23)C1

Standard InChI:  InChI=1S/C23H28N8O2/c1-4-18(32)30(3)17-10-8-15(9-11-17)27-23-28-21-20(24-14-25-21)22(29-23)26-16-7-6-12-31(13-16)19(33)5-2/h5,8-11,14,16H,2,4,6-7,12-13H2,1,3H3,(H3,24,25,26,27,28,29)

Standard InChI Key:  OTPQDXLFXQGSHS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   -2.6264    0.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6276   -0.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9128   -0.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1963   -0.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1992    0.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9146    0.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4812   -0.8007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2326   -0.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9444   -0.7989    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367    0.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263    0.4358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434    0.6907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6569    0.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6535   -0.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4389   -0.6436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9251    0.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9325    1.6761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6449    2.0922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3601    1.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0703    2.0904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0704    2.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3539    3.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6375    2.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7853    1.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7864    0.8539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4992    2.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2143    1.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3410    0.8499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3412    1.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0554    0.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7699    0.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0552   -0.3878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4843    0.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
 16 12  2  0
  7  8  1  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
  8  9  2  0
  9 14  1  0
  4  5  1  0
 13 10  1  0
  2  3  1  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 10 11  2  0
 20 24  1  0
 11  8  1  0
 24 25  2  0
 13 14  2  0
 24 26  1  0
  5  6  2  0
 26 27  2  0
  6  1  1  0
  1 28  1  0
  1  2  2  0
 28 29  1  0
  4  7  1  0
 28 30  1  0
  3  4  2  0
 30 31  1  0
 12 13  1  0
 30 32  2  0
 14 15  1  0
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1643959

   N-methyl-N-[4-[[6-[[1-(1-oxoprop-2-enyl)-3-piperidinyl]amino]-7H-purin-2-yl]amino]phenyl]propanamide

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: 448.53

Molecular Weight (Monoisotopic): 448.2335

AlogP: 3.06

#Rotatable Bonds: 7

Polar Surface Area: 119.14

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.71

CX Basic pKa: 4.96

CX LogP: 2.16

CX LogD: 2.16

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.48

Np Likeness Score: -1.33

References

1. Zhou W, Ercan D, Jänne PA, Gray NS..  (2011)  Discovery of selective irreversible inhibitors for EGFR-T790M.,  21  (2): [PMID:21208802] [10.1016/j.bmcl.2010.12.036]

2. Genomics of Drug Sensitity in Cancer screening data, Wellcome Trust Sanger Institute,  [10.6019/CHEMBL1201861]

Source

Source(2):

• Scientific Literature
• Sanger Institute Genomics of Drug Sensitivity in Cancer