4-Ethoxy-5-methyl-1-(4-nitrobenzyl)pyrimidin-2(1H)-one

ID: ALA4451518

PubChem CID: 151054513

Max Phase: Preclinical

Molecular Formula: C14H15N3O4

Molecular Weight: 289.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOc1nc(=O)n(Cc2ccc([N+](=O)[O-])cc2)cc1C

Standard InChI:  InChI=1S/C14H15N3O4/c1-3-21-13-10(2)8-16(14(18)15-13)9-11-4-6-12(7-5-11)17(19)20/h4-8H,3,9H2,1-2H3

Standard InChI Key:  MEVBYVJDWUPJRT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    8.5750  -25.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5738  -26.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2819  -26.4169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9915  -26.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9887  -25.1848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2801  -24.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8672  -24.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2776  -23.9624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9841  -23.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9817  -22.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6999  -26.4150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2817  -27.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9893  -27.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9849  -28.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6917  -28.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4005  -28.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3981  -27.6371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6907  -27.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1123  -28.8649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8195  -28.4555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1131  -29.6821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  4 11  2  0
  3 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 19 20  2  0
 19 21  1  0
 16 19  1  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4451518

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 289.29

Molecular Weight (Monoisotopic): 289.1063

AlogP: 1.91

#Rotatable Bonds: 5

Polar Surface Area: 87.26

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.27

CX LogD: 2.27

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.62

Np Likeness Score: -1.42

References

1. Trifonov L, Nudelman V, Zhenin M, Matsree E, Afri M, Schmerling B, Cohen G, Jozwiak K, Weitman M, Korshin E, Senderowitz H, Shainberg A, Hochhauser E, Gruzman A..  (2018)  Structurally Simple, Readily Available Peptidomimetic 1-Benzyl-5-methyl-4-( n-octylamino)pyrimidin-2(1 H)-one Exhibited Efficient Cardioprotection in a Myocardial Ischemia (MI) Mouse Model.,  61  (24): [PMID:30507195] [10.1021/acs.jmedchem.8b01471]

Source

Source(1):

• Scientific Literature