4-amino-7-((1-(2-(quinolin-4-ylamino)ethyl)piperidin-4-yl)methoxy)quinazoline

ID: ALA4101056

PubChem CID: 117967751

Max Phase: Preclinical

Molecular Formula: C25H28N6O

Molecular Weight: 428.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2cc(OCC3CCN(CCNc4ccnc5ccccc45)CC3)ccc12

Standard InChI:  InChI=1S/C25H28N6O/c26-25-21-6-5-19(15-24(21)29-17-30-25)32-16-18-8-12-31(13-9-18)14-11-28-23-7-10-27-22-4-2-1-3-20(22)23/h1-7,10,15,17-18H,8-9,11-14,16H2,(H,27,28)(H2,26,29,30)

Standard InChI Key:  JOHLZKNZLYHHAQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   24.3545  -20.2715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0683  -19.8621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0655  -19.0394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3527  -18.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6465  -19.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6487  -19.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9428  -18.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2341  -19.0433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2358  -19.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9423  -20.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3492  -17.8169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5291  -20.2744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8204  -19.8675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1136  -20.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4067  -19.8675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7021  -20.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6998  -21.0918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4083  -21.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1191  -21.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9915  -21.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2844  -21.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5761  -21.4974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8690  -21.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4529  -20.2696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4544  -21.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1654  -21.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1647  -19.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8714  -20.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5792  -19.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5815  -19.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8701  -18.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1652  -19.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  5  2  0
  4 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 28  2  0
 27 24  2  0
 24 25  1  0
 25 26  2  0
 26 23  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4101056

   4-Amino-7-((1-(2-(quinolin-4-ylamino)ethyl)piperidin-4-yl)methoxy)quinazoline

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: 428.54

Molecular Weight (Monoisotopic): 428.2325

AlogP: 3.96

#Rotatable Bonds: 7

Polar Surface Area: 89.19

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.00

CX LogP: 2.95

CX LogD: 0.90

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.46

Np Likeness Score: -1.23

References

1. Halby L, Menon Y, Rilova E, Pechalrieu D, Masson V, Faux C, Bouhlel MA, David-Cordonnier MH, Novosad N, Aussagues Y, Samson A, Lacroix L, Ausseil F, Fleury L, Guianvarc'h D, Ferroud C, Arimondo PB..  (2017)  Rational Design of Bisubstrate-Type Analogues as Inhibitors of DNA Methyltransferases in Cancer Cells.,  60  (11): [PMID:28463515] [10.1021/acs.jmedchem.7b00176]

Source

Source(1):

• Scientific Literature