3-{2,4-Dioxo-1-[(4-sulfamoylphenyl)methyl]-1,2,3,4-tetrahydropyrimidin-5-yl}-N-[(4-fluoro-3-methoxyphenyl)-methyl]prop-2-ynamide

ID: ALA4095780

PubChem CID: 137654086

Max Phase: Preclinical

Molecular Formula: C22H19FN4O6S

Molecular Weight: 486.48

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H19FN4O6S/c1-33-19-10-15(4-8-18(19)23)11-25-20(28)9-5-16-13-27(22(30)26-21(16)29)12-14-2-6-17(7-3-14)34(24,31)32/h2-4,6-8,10,13H,11-12H2,1H3,(H,25,28)(H2,24,31,32)(H,26,29,30)

Standard InChI Key:  FTDANXPNKJENKV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
   33.8928   -1.9357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3055   -2.6456    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   34.7139   -1.9332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.8436   -3.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8436   -3.8663    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.5557   -4.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2574   -3.8663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2574   -3.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5557   -2.6282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.9682   -4.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6787   -4.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1302   -2.6334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.9709   -2.6334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.3927   -5.0998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3892   -5.9190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.1019   -4.6923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.8159   -5.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5293   -4.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.2347   -5.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.9432   -4.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.9505   -3.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.2362   -3.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5279   -3.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.2384   -2.6548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.1399   -4.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4287   -3.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4298   -3.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7240   -2.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0147   -3.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0179   -3.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7287   -4.2823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.9472   -2.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.6605   -3.4819    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   33.5993   -3.0596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  4  9  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  3  0
  4 12  2  0
  8 13  2  0
 11 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 22 24  1  0
  5 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 24 32  1  0
 21 33  1  0
 29  2  1  0
  2 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4095780

   ---

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: 486.48

Molecular Weight (Monoisotopic): 486.1009

AlogP: 0.05

#Rotatable Bonds: 6

Polar Surface Area: 153.35

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.41

CX Basic pKa: ┄

CX LogP: 0.89

CX LogD: 0.88

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.42

Np Likeness Score: -1.28

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