4-Oxo-N-((3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)methyl)-5-(4-(trifluoromethyl)phenyl)-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide

ID: ALA4069479

PubChem CID: 137632187

Max Phase: Preclinical

Molecular Formula: C23H15F3N4O4S

Molecular Weight: 500.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1COc2ccc(CNC(=O)c3nc4scc(-c5ccc(C(F)(F)F)cc5)c4c(=O)[nH]3)cc2N1

Standard InChI:  InChI=1S/C23H15F3N4O4S/c24-23(25,26)13-4-2-12(3-5-13)14-10-35-22-18(14)20(32)29-19(30-22)21(33)27-8-11-1-6-16-15(7-11)28-17(31)9-34-16/h1-7,10H,8-9H2,(H,27,33)(H,28,31)(H,29,30,32)

Standard InChI Key:  GUEZUXNRTRXDAO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   14.0008   -5.0488    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.8044   -5.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5484   -4.4371    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.7842   -9.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4933   -9.8604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   14.4598   -9.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9755   -9.7065    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.0793   -9.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0793  -10.6776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8330   -8.2260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8330   -7.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5380   -7.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2471   -7.4088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2471   -8.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5380   -8.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9520   -8.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9520   -9.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2471   -9.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5380   -9.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5380   -6.1830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4933   -7.4088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5948   -5.0020    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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  4 13  1  0
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 23 28  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 28 32  2  0
 27 29  2  0
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 22 30  1  0
 15 22  1  0
  8 34  2  0
 19  2  1  0
  2 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4069479

   ---

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: 500.46

Molecular Weight (Monoisotopic): 500.0766

AlogP: 3.93

#Rotatable Bonds: 4

Polar Surface Area: 113.18

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.36

CX Basic pKa: ┄

CX LogP: 3.13

CX LogD: 2.86

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.39

Np Likeness Score: -1.58

References

1. Mahasenan KV, Bastian M, Gao M, Frost E, Ding D, Zorina-Lichtenwalter K, Jacobs J, Suckow MA, Schroeder VA, Wolter WR, Chang M, Mobashery S..  (2017)  Exploitation of Conformational Dynamics in Imparting Selective Inhibition for Related Matrix Metalloproteinases.,  8  (6): [PMID:28626528] [10.1021/acsmedchemlett.7b00130]

Source

Source(1):

• Scientific Literature