N-[(4-Fluoro-3-methoxyphenyl)methyl]-3-(1-{[4-(1,3-oxazol-5-yl)phenyl]methyl}-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)prop-2-ynamide

ID: ALA4071820

PubChem CID: 137638970

Max Phase: Preclinical

Molecular Formula: C25H19FN4O5

Molecular Weight: 474.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(CNC(=O)C#Cc2cn(Cc3ccc(-c4cnco4)cc3)c(=O)[nH]c2=O)ccc1F

Standard InChI:  InChI=1S/C25H19FN4O5/c1-34-21-10-17(4-8-20(21)26)11-28-23(31)9-7-19-14-30(25(33)29-24(19)32)13-16-2-5-18(6-3-16)22-12-27-15-35-22/h2-6,8,10,12,14-15H,11,13H2,1H3,(H,28,31)(H,29,32,33)

Standard InChI Key:  XHWPSFKZEOYPJH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
   22.1436   -3.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1436   -4.1511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8557   -4.5554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5575   -4.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5575   -3.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8557   -2.9130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2682   -4.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9787   -4.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4302   -2.9182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2709   -2.9182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6927   -5.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6892   -6.2038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4019   -4.9771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.1160   -5.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8293   -4.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5347   -5.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2432   -4.9909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2505   -4.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5362   -3.7566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8280   -4.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5384   -2.9395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8300   -2.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9584   -3.7650    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.4399   -4.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7287   -4.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7299   -3.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0241   -2.9322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3147   -3.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3179   -4.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0287   -4.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6064   -2.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5194   -2.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7197   -1.9543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3125   -2.6628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8605   -3.2690    0.0000 O   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
 21 22  1  0
 18 23  1  0
  2 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 31  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4071820

   ---

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: 474.45

Molecular Weight (Monoisotopic): 474.1339

AlogP: 2.06

#Rotatable Bonds: 6

Polar Surface Area: 119.22

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: 0.78

CX LogP: 1.79

CX LogD: 1.79

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.41

Np Likeness Score: -1.09

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