2-(3-Bromo-4,5-dimethoxyphenyl)-7-ethoxycarbonyl)-5,6,7,8-tetrahydropyridylthieno[2,3-djpyrimidin-4(3H)-one

ID: ALA4759455

PubChem CID: 162657772

Max Phase: Preclinical

Molecular Formula: C20H20BrN3O5S

Molecular Weight: 494.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)N1CCc2c(sc3nc(-c4cc(Br)c(OC)c(OC)c4)[nH]c(=O)c23)C1

Standard InChI:  InChI=1S/C20H20BrN3O5S/c1-4-29-20(26)24-6-5-11-14(9-24)30-19-15(11)18(25)22-17(23-19)10-7-12(21)16(28-3)13(8-10)27-2/h7-8H,4-6,9H2,1-3H3,(H,22,23,25)

Standard InChI Key:  DTDPRYPGXLQTLC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    5.5181  -28.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5181  -29.4148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2275  -29.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2275  -28.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9369  -28.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9414  -29.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7207  -29.6626    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7135  -28.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1905  -28.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9952  -28.9105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3291  -28.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8480  -27.5094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0370  -27.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1436  -28.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6238  -28.7459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4399  -28.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7768  -27.9091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2875  -27.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4731  -27.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5546  -26.9303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5935  -27.8223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0750  -28.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9191  -29.3225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5855  -30.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6157  -26.4979    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.8106  -29.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1027  -29.4155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3952  -29.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6873  -29.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8110  -30.6409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  6  7  1  0
  7  9  1  0
  8  5  1  0
  8  9  2  0
  8 13  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 11 14  1  0
 13 20  2  0
 17 21  1  0
 21 22  1  0
 16 23  1  0
 23 24  1  0
 18 25  1  0
  2 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 26 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4759455

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 494.37

Molecular Weight (Monoisotopic): 493.0307

AlogP: 3.95

#Rotatable Bonds: 4

Polar Surface Area: 93.75

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.03

CX Basic pKa: 0.47

CX LogP: 3.34

CX LogD: 3.26

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.59

Np Likeness Score: -1.41

References

1. Gold M,Köhler L,Lanzloth C,Andronache I,Anant S,Dandawate P,Biersack B,Schobert R.  (2020)  Synthesis and bioevaluation of new vascular-targeting and anti-angiogenic thieno[2,3-d]pyrimidin-4(3H)-ones.,  189  [PMID:31958738] [10.1016/j.ejmech.2020.112060]

Source

Source(1):

• Scientific Literature