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

ID: ALA4104422

PubChem CID: 137657100

Max Phase: Preclinical

Molecular Formula: C24H20N4O4S

Molecular Weight: 460.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1COc2ccc(CNC(=O)c3nc4scc(CCc5ccccc5)c4c(=O)[nH]3)cc2N1

Standard InChI:  InChI=1S/C24H20N4O4S/c29-19-12-32-18-9-7-15(10-17(18)26-19)11-25-23(31)21-27-22(30)20-16(13-33-24(20)28-21)8-6-14-4-2-1-3-5-14/h1-5,7,9-10,13H,6,8,11-12H2,(H,25,31)(H,26,29)(H,27,28,30)

Standard InChI Key:  CSGNSDMLNGXHMQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   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
   13.2024   -9.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2024   -8.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4933   -8.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7842   -8.6346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9753   -8.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   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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    9.6611   -9.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
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    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
   14.2252   -7.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0240   -7.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2739   -6.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0717   -6.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3217   -5.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7726   -5.0972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9703   -5.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7240   -6.0502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
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  5  6  1  0
  1  6  1  0
  7  8  2  0
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  3  9  1  0
  4  7  1  0
 10 11  2  0
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  1 10  1  0
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 14 19  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 19 23  2  0
 18 20  2  0
 16 24  2  0
 13 21  1  0
 12 13  1  0
  5 25  2  0
  7 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4104422

   ---

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: 460.52

Molecular Weight (Monoisotopic): 460.1205

AlogP: 3.03

#Rotatable Bonds: 6

Polar Surface Area: 113.18

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.43

CX Basic pKa: ┄

CX LogP: 3.14

CX LogD: 2.90

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.41

Np Likeness Score: -1.20

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