Ethyl 2-((2-chlorobenzyl)amino)-4-hydroxypyrimidine-5-carboxylate

ID: ALA4552197

PubChem CID: 89880314

Max Phase: Preclinical

Molecular Formula: C14H14ClN3O3

Molecular Weight: 307.74

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cnc(NCc2ccccc2Cl)nc1O

Standard InChI:  InChI=1S/C14H14ClN3O3/c1-2-21-13(20)10-8-17-14(18-12(10)19)16-7-9-5-3-4-6-11(9)15/h3-6,8H,2,7H2,1H3,(H2,16,17,18,19)

Standard InChI Key:  KMFRKDADVDLIIB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    6.4371   -7.5610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4359   -8.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1440   -8.7895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8536   -8.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8508   -7.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1422   -7.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1397   -6.3350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5570   -7.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2662   -7.5521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5539   -6.3290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7279   -8.7886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0205   -8.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3192   -8.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6173   -8.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9165   -8.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9194   -9.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6289  -10.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3268   -9.5942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0381   -9.9966    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.9724   -7.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6816   -7.5468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  8 10  2  0
  2 11  1  0
 11 12  1  0
 13 12  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
 18 19  1  0
  9 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4552197

   ethyl 2-[(2-chlorophenyl)methylamino]-6-oxo-1H-pyrimidine-5-carboxylate

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: 307.74

Molecular Weight (Monoisotopic): 307.0724

AlogP: 2.62

#Rotatable Bonds: 5

Polar Surface Area: 84.34

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.53

CX Basic pKa: 1.74

CX LogP: 3.83

CX LogD: 3.83

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.83

Np Likeness Score: -1.68

References

1. Watkins SM, Ghose D, Blain JM, Grote DL, Luan CH, Clare M, Meganathan R, Horn JR, Hagen TJ..  (2019)  Antibacterial activity of 2-amino-4-hydroxypyrimidine-5-carboxylates and binding to Burkholderia pseudomallei 2-C-methyl-d-erythritol-2,4-cyclodiphosphate synthase.,  29  (20): [PMID:31521478] [10.1016/j.bmcl.2019.126660]

Source

Source(1):

• Scientific Literature