Ethyl 2-((3-chlorobenzyl)amino)-4-hydroxypyrimidine-5-carboxylate

ID: ALA4585815

PubChem CID: 89880315

Max Phase: Preclinical

Molecular Formula: C14H14ClN3O3

Molecular Weight: 307.74

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cnc(NCc2cccc(Cl)c2)nc1O

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

Standard InChI Key:  FAFBONAZPNVWBP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   36.1779  -17.8874    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.1767  -18.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8848  -19.1159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.5944  -18.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5916  -17.8838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8830  -17.4785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8805  -16.6613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.2978  -17.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0070  -17.8784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.2947  -16.6553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.4687  -19.1149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.7613  -18.7058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0600  -19.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3581  -18.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6573  -19.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6602  -19.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3698  -20.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0676  -19.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3760  -21.1480    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   39.7132  -17.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4224  -17.8731    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
 17 19  1  0
  9 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4585815

   ethyl 2-[(3-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: 12.54

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