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}-N,N-dimethylbenzamide

ID: ALA4097812

PubChem CID: 137659945

Max Phase: Preclinical

Molecular Formula: C25H23FN4O5

Molecular Weight: 478.48

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H23FN4O5/c1-29(2)24(33)18-7-4-16(5-8-18)14-30-15-19(23(32)28-25(30)34)9-11-22(31)27-13-17-6-10-20(26)21(12-17)35-3/h4-8,10,12,15H,13-14H2,1-3H3,(H,27,31)(H,28,32,34)

Standard InChI Key:  UEGUSCZBRJCYEP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
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   20.4391   -9.4009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1512   -9.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8529   -9.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8529   -8.5776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1512   -8.1628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5637   -9.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2741  -10.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7256   -8.1680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5664   -8.1680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9881  -10.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9847  -11.4536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6974  -10.2269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.4114  -10.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1248  -10.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8302  -10.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5387  -10.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   26.8339   -8.1894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7354   -9.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0242   -9.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0253   -8.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3195   -8.1821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6102   -8.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6134   -9.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3242   -9.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9017   -8.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9001   -7.3671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5427   -7.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2560   -9.0165    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.1948   -8.5942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1963   -9.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4863   -8.1869    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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 14 15  1  0
 15 16  2  0
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 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
 33 34  1  0
 33 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4097812

   ---

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: 478.48

Molecular Weight (Monoisotopic): 478.1652

AlogP: 1.10

#Rotatable Bonds: 6

Polar Surface Area: 113.50

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.49

CX Basic pKa: ┄

CX LogP: 1.58

CX LogD: 1.57

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.52

Np Likeness Score: -1.26

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