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

ID: ALA4100095

PubChem CID: 117967660

Max Phase: Preclinical

Molecular Formula: C33H37N7O

Molecular Weight: 547.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1ccc(NCCNc2ncnc3cc(OCC4CCN(CCNc5ccnc6ccccc56)CC4)ccc23)cc1

Standard InChI:  InChI=1S/C33H37N7O/c1-2-6-26(7-3-1)34-16-17-37-33-29-11-10-27(22-32(29)38-24-39-33)41-23-25-13-19-40(20-14-25)21-18-36-31-12-15-35-30-9-5-4-8-28(30)31/h1-12,15,22,24-25,34H,13-14,16-21,23H2,(H,35,36)(H,37,38,39)

Standard InChI Key:  IOFQDXBHAKWMAD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 41 46  0  0  0  0  0  0  0  0999 V2000
   37.6277  -20.2385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.3415  -19.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3386  -19.0064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.6259  -18.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9196  -19.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9219  -19.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2160  -18.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5073  -19.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5090  -19.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2155  -20.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6224  -17.7839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.9129  -17.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2070  -17.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8022  -20.2414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.0935  -19.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3868  -20.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6799  -19.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9752  -20.2413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9729  -21.0588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6815  -21.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3923  -21.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2647  -21.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5575  -21.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8492  -21.4644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1421  -21.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7261  -20.2366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.7276  -21.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4386  -21.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4379  -19.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1446  -20.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8523  -19.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8546  -19.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1432  -18.6063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4384  -19.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4975  -17.3844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.7916  -17.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0852  -17.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3797  -17.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3828  -18.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0972  -19.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7997  -18.6113    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
 11 12  1  0
 12 13  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 30  2  0
 29 26  2  0
 26 27  1  0
 27 28  2  0
 28 25  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
 13 35  1  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100095

   N-phenyl-N'-[7-[[1-[2-(quinolin-4-ylamino)ethyl]piperidin-4-yl]methoxy]quinazolin-4-yl]ethane-1,2-diamine

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: 547.71

Molecular Weight (Monoisotopic): 547.3060

AlogP: 5.90

#Rotatable Bonds: 12

Polar Surface Area: 87.23

Molecular Species: BASE

HBA: 8

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 9.00

CX LogP: 4.53

CX LogD: 2.48

Aromatic Rings: 5

Heavy Atoms: 41

QED Weighted: 0.17

Np Likeness Score: -1.31

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