3-(2,4-diaminopyrimidin-5-yl)-1-(4-(4-methylbenzyloxy)phenyl)prop-2-en-1-one

ID: ALA1096524

PubChem CID: 46888230

Max Phase: Preclinical

Molecular Formula: C21H20N4O2

Molecular Weight: 360.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(COc2ccc(C(=O)/C=C/c3cnc(N)nc3N)cc2)cc1

Standard InChI:  InChI=1S/C21H20N4O2/c1-14-2-4-15(5-3-14)13-27-18-9-6-16(7-10-18)19(26)11-8-17-12-24-21(23)25-20(17)22/h2-12H,13H2,1H3,(H4,22,23,24,25)/b11-8+

Standard InChI Key:  UPIRPTAUDCZLPJ-DHZHZOJOSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    1.1319   -4.9291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1307   -5.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8455   -6.1693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5620   -5.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5591   -4.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8437   -4.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4159   -6.1684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8413   -3.6913    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2720   -4.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9880   -4.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7010   -4.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4170   -4.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6978   -3.6799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4170   -5.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1321   -6.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8460   -5.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8403   -4.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1245   -4.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5623   -6.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2747   -5.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9913   -6.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9931   -6.9594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7088   -7.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4221   -6.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4152   -6.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6990   -5.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1393   -7.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  2  0
  2  7  1  0
 14 15  1  0
  3  4  2  0
 15 16  2  0
  6  8  1  0
 16 17  1  0
 17 18  2  0
 18 12  1  0
  5  9  1  0
  4  5  1  0
 19 20  1  0
 16 19  1  0
  9 10  2  0
 20 21  1  0
  2  3  1  0
 21 22  2  0
 10 11  1  0
 22 23  1  0
  5  6  2  0
 23 24  2  0
 11 12  1  0
 24 25  1  0
  6  1  1  0
 25 26  2  0
 26 21  1  0
 11 13  2  0
  1  2  2  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1096524

   3-(2,4-Diaminophenyl)-1-(3-(4-methylbenzyloxy)phenyl)prop-2-en-1-one

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: 360.42

Molecular Weight (Monoisotopic): 360.1586

AlogP: 3.42

#Rotatable Bonds: 6

Polar Surface Area: 104.12

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.27

CX LogP: 3.66

CX LogD: 3.43

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: -0.56

References

1. Bag S, Tawari NR, Degani MS, Queener SF..  (2010)  Design, synthesis, biological evaluation and computational investigation of novel inhibitors of dihydrofolate reductase of opportunistic pathogens.,  18  (9): [PMID:20363634] [10.1016/j.bmc.2010.03.031]

Source

Source(1):

• Scientific Literature