Methyl 4-{[5-(2-{[(4-Fluoro-3-methoxyphenyl)methyl]-carbamoyl}eth-1-yn-1-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl]methyl}benzoate

ID: ALA4101280

PubChem CID: 137658673

Max Phase: Preclinical

Molecular Formula: C24H20FN3O6

Molecular Weight: 465.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(Cn2cc(C#CC(=O)NCc3ccc(F)c(OC)c3)c(=O)[nH]c2=O)cc1

Standard InChI:  InChI=1S/C24H20FN3O6/c1-33-20-11-16(5-9-19(20)25)12-26-21(29)10-8-18-14-28(24(32)27-22(18)30)13-15-3-6-17(7-4-15)23(31)34-2/h3-7,9,11,14H,12-13H2,1-2H3,(H,26,29)(H,27,30,32)

Standard InChI Key:  BJBJSCJDKGVTKQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
   34.7564   -8.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7564   -9.7723    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.4685  -10.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1703   -9.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1703   -8.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4685   -8.5342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.8810  -10.1804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5915  -10.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0430   -8.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.8837   -8.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.3055  -11.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3020  -11.8251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.0147  -10.5983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.7288  -11.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4421  -10.6044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1475  -11.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   41.8633   -9.7926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1490   -9.3779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4408   -9.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1512   -8.5608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.0527  -10.1817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3415   -9.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3427   -8.9611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6369   -8.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9275   -8.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9307   -9.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6415  -10.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2191   -8.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2175   -7.7385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.8600   -8.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5733   -9.3880    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.5121   -8.9656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8036   -8.5584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  4  7  1  0
  7  8  3  0
  1  9  2  0
  5 10  2  0
  8 11  1  0
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 11 13  1  0
 13 14  1  0
 14 15  1  0
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 17 18  2  0
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 19 20  2  0
 20 15  1  0
 19 21  1  0
  2 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26 29  1  0
 29 30  2  0
 21 31  1  0
 18 32  1  0
 29 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4101280

   ---

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: 465.44

Molecular Weight (Monoisotopic): 465.1336

AlogP: 1.19

#Rotatable Bonds: 6

Polar Surface Area: 119.49

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.49

CX Basic pKa: ┄

CX LogP: 2.28

CX LogD: 2.28

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.42

Np Likeness Score: -0.95

References

1. Senn N, Ott M, Lanz J, Riedl R..  (2017)  Targeted Polypharmacology: Discovery of a Highly Potent Non-Hydroxamate Dual Matrix Metalloproteinase (MMP)-10/-13 Inhibitor.,  60  (23): [PMID:28953404] [10.1021/acs.jmedchem.7b01001]

Source

Source(1):

• Scientific Literature