5-Methyl-1-(4-nitrobenzyl)-4-(n-octylamino)pyrimidin-2(1H)-one

ID: ALA4460648

PubChem CID: 149278385

Max Phase: Preclinical

Molecular Formula: C20H28N4O3

Molecular Weight: 372.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCCCNc1nc(=O)n(Cc2ccc([N+](=O)[O-])cc2)cc1C

Standard InChI:  InChI=1S/C20H28N4O3/c1-3-4-5-6-7-8-13-21-19-16(2)14-23(20(25)22-19)15-17-9-11-18(12-10-17)24(26)27/h9-12,14H,3-8,13,15H2,1-2H3,(H,21,22,25)

Standard InChI Key:  XSLWLUSAZUSEMO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   14.4769  -12.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4758  -13.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1838  -13.7587    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8935  -13.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8906  -12.5266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1820  -12.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7691  -12.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6018  -13.7568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1836  -14.5759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1796  -11.3042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8912  -14.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8869  -15.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5937  -16.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3024  -15.8003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3000  -14.9789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5927  -14.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8861  -10.8935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5950  -11.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3015  -10.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0104  -11.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7169  -10.8850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4258  -11.2915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1323  -10.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8412  -11.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0142  -16.2067    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7215  -15.7973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0151  -17.0239    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
  4  8  2  0
  3  9  1  0
  6 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 25 26  2  0
 25 27  1  0
 14 25  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4460648

   ---

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: 372.47

Molecular Weight (Monoisotopic): 372.2161

AlogP: 4.28

#Rotatable Bonds: 11

Polar Surface Area: 90.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.43

CX LogD: 4.43

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.36

Np Likeness Score: -1.03

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