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

ID: ALA1094564

PubChem CID: 46888229

Max Phase: Preclinical

Molecular Formula: C14H14N4O2

Molecular Weight: 270.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C(=O)/C=C/c2cnc(N)nc2N)cc1

Standard InChI:  InChI=1S/C14H14N4O2/c1-20-11-5-2-9(3-6-11)12(19)7-4-10-8-17-14(16)18-13(10)15/h2-8H,1H3,(H4,15,16,17,18)/b7-4+

Standard InChI Key:  HPQVWFWQLGFBDK-QPJJXVBHSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   13.1527   -6.2750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1516   -7.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8664   -7.5152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5828   -7.1019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5800   -6.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8646   -5.8622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4368   -7.5143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8621   -5.0372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2929   -5.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0089   -6.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7218   -5.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4378   -6.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7187   -5.0258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4378   -7.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1530   -7.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8669   -7.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8611   -6.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1454   -5.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5832   -7.4876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2956   -7.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  2  0
  2  3  1  0
 10 11  1  0
  5  6  2  0
 11 12  1  0
  6  1  1  0
 11 13  2  0
  1  2  2  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
M  END

Alternative Forms

1. Parent:

   

   ALA1094564

   3-(2,4-Diaminopyrimidin-5-yl)-1-(4-methoxyphenyl)-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: 270.29

Molecular Weight (Monoisotopic): 270.1117

AlogP: 1.55

#Rotatable Bonds: 4

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: 1.42

CX LogD: 1.20

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.64

Np Likeness Score: -0.32

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