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}benzamide

ID: ALA4091076

PubChem CID: 137642170

Max Phase: Preclinical

Molecular Formula: C23H19FN4O5

Molecular Weight: 450.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(CNC(=O)C#Cc2cn(Cc3ccc(C(N)=O)cc3)c(=O)[nH]c2=O)ccc1F

Standard InChI:  InChI=1S/C23H19FN4O5/c1-33-19-10-15(4-8-18(19)24)11-26-20(29)9-7-17-13-28(23(32)27-22(17)31)12-14-2-5-16(6-3-14)21(25)30/h2-6,8,10,13H,11-12H2,1H3,(H2,25,30)(H,26,29)(H,27,31,32)

Standard InChI Key:  DEHOOGQJQMRJJL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   36.9769   -2.9522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9769   -3.7755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.6890   -4.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3907   -3.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3907   -2.9522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6890   -2.5374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.1015   -4.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8119   -4.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2634   -2.5426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.1042   -2.5426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.5260   -5.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5225   -5.8282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.2352   -4.6015    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.9492   -5.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6626   -4.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3680   -5.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0765   -4.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0838   -3.7957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3695   -3.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6612   -3.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3717   -2.5640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2732   -4.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5620   -3.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5631   -2.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8573   -2.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1480   -2.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1512   -3.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8620   -4.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4395   -2.5588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4380   -1.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.0805   -2.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.7938   -3.3911    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.7326   -2.9688    0.0000 N   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
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 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
M  END

Alternative Forms

1. Parent:

   

   ALA4091076

   ---

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: 450.43

Molecular Weight (Monoisotopic): 450.1339

AlogP: 0.50

#Rotatable Bonds: 6

Polar Surface Area: 136.28

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.49

CX Basic pKa: ┄

CX LogP: 1.13

CX LogD: 1.13

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.47

Np Likeness Score: -1.11

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