2-(3-Bromo-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydropyridylthieno[2,3-d]pyrimidin-4(3H)-one trifluoroacetic acid

ID: ALA4763475

PubChem CID: 162659164

Max Phase: Preclinical

Molecular Formula: C19H17BrF3N3O5S

Molecular Weight: 422.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(-c2nc3sc4c(c3c(=O)[nH]2)CCNC4)cc(Br)c1OC.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C17H16BrN3O3S.C2HF3O2/c1-23-11-6-8(5-10(18)14(11)24-2)15-20-16(22)13-9-3-4-19-7-12(9)25-17(13)21-15;3-2(4,5)1(6)7/h5-6,19H,3-4,7H2,1-2H3,(H,20,21,22);(H,6,7)

Standard InChI Key:  JARMNLONTWZJHI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   20.7193  -14.6492    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.1323  -15.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5410  -14.6467    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.4261  -15.7727    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.8426  -15.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5508  -15.3638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8426  -16.5905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8636  -15.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8636  -16.0205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5788  -16.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5788  -14.7764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2940  -15.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2985  -16.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0843  -16.2704    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.0770  -14.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5580  -15.5985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3693  -15.5122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7059  -14.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2209  -14.0996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4033  -14.1849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5271  -14.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0113  -15.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8341  -15.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1738  -14.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6804  -13.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8594  -13.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9169  -13.5156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9972  -14.4151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4826  -15.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3172  -15.9275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9809  -16.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0113  -13.0798    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  2  1  0
  2  5  1  0
  5  6  1  0
  5  7  2  0
  8  9  1  0
  8 11  1  0
  9 10  1  0
 10 13  1  0
 12 11  1  0
 12 13  2  0
 13 14  1  0
 14 16  1  0
 15 12  1  0
 15 16  2  0
 15 20  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 18 21  1  0
 20 27  2  0
 24 28  1  0
 28 29  1  0
 23 30  1  0
 30 31  1  0
 25 32  1  0
M  END

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: 422.30

Molecular Weight (Monoisotopic): 421.0096

AlogP: 3.08

#Rotatable Bonds: 3

Polar Surface Area: 76.24

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.83

CX Basic pKa: 8.47

CX LogP: 2.11

CX LogD: 1.81

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.68

Np Likeness Score: -1.01

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