N2-Cyclohexyl-6,7-dimethoxy-N4-(1-methylpiperidin-4-yl)quinazoline-2,4-diamine

ID: ALA4083783

PubChem CID: 137648196

Max Phase: Preclinical

Molecular Formula: C22H33N5O2

Molecular Weight: 399.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2nc(NC3CCCCC3)nc(NC3CCN(C)CC3)c2cc1OC

Standard InChI:  InChI=1S/C22H33N5O2/c1-27-11-9-16(10-12-27)23-21-17-13-19(28-2)20(29-3)14-18(17)25-22(26-21)24-15-7-5-4-6-8-15/h13-16H,4-12H2,1-3H3,(H2,23,24,25,26)

Standard InChI Key:  FNDUCTFWOZQGTB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    5.8923  -12.9099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8911  -13.7295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5992  -14.1384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5974  -12.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3060  -12.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3068  -13.7253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0153  -14.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7236  -13.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7188  -12.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0097  -12.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5949  -11.6839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4240  -12.4866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1342  -12.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4328  -14.1274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1390  -13.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8860  -11.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8862  -10.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1813  -10.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4724  -10.4576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4729  -11.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1823  -11.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7650  -10.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1831  -14.1375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4757  -13.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4757  -12.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7724  -12.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0620  -12.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0594  -13.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7672  -14.1387    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 10  2  0
 10  5  1  0
  4 11  1  0
  9 12  1  0
 12 13  1  0
  8 14  1  0
 14 15  1  0
 11 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
  2 23  1  0
 23 24  1  0
 24 25  1  0
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4083783

   ---

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: 399.54

Molecular Weight (Monoisotopic): 399.2634

AlogP: 3.90

#Rotatable Bonds: 6

Polar Surface Area: 71.54

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.77

CX LogP: 3.15

CX LogD: 1.57

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.76

Np Likeness Score: -0.81

References

1. Xiong Y, Li F, Babault N, Wu H, Dong A, Zeng H, Chen X, Arrowsmith CH, Brown PJ, Liu J, Vedadi M, Jin J..  (2017)  Structure-activity relationship studies of G9a-like protein (GLP) inhibitors.,  25  (16): [PMID:28662962] [10.1016/j.bmc.2017.06.021]

Source

Source(1):

• Scientific Literature