2-(4-(2-Methoxyphenyl)piperazin-1-yl)-3,5,7,8-tetrahydro-4H-thiopyrano[4,3-d]pyrimidin-4-one 6-oxide

ID: ALA4556137

PubChem CID: 155556919

Max Phase: Preclinical

Molecular Formula: C18H22N4O3S

Molecular Weight: 374.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccccc1N1CCN(c2nc3c(c(=O)[nH]2)C[S+]([O-])CC3)CC1

Standard InChI:  InChI=1S/C18H22N4O3S/c1-25-16-5-3-2-4-15(16)21-7-9-22(10-8-21)18-19-14-6-11-26(24)12-13(14)17(23)20-18/h2-5H,6-12H2,1H3,(H,19,20,23)

Standard InChI Key:  FNWSNPIZSCHHJZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   10.1533   -7.5158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7364   -7.5158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9863   -9.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4443   -6.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9904   -7.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5737   -6.6931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1070  -10.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8600   -5.4584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4076   -9.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8256   -9.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8622   -6.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5748   -7.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6992   -8.7498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1563   -6.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2801   -8.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1215   -7.9344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7013   -7.9279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7364   -6.6949    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.2822   -7.9244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4443   -7.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8643   -7.9210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8380   -7.5254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8307   -9.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4023   -9.9837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1174   -8.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0270   -6.2893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 25 16  1  0
 14  1  2  0
  6 11  1  0
 24  7  1  0
 12 19  1  0
  9 25  1  0
 17  5  1  0
 20  1  1  0
 21 12  2  0
  1 21  1  0
 12  6  1  0
 15  3  1  0
 11  8  2  0
 18  4  1  0
  2 20  1  0
 18  2  1  0
 10 23  1  0
 19 15  1  0
 13  9  1  0
  9 24  2  0
 13 17  1  0
 16 22  1  0
 14 11  1  0
 19  5  1  0
  3 13  1  0
 23 25  2  0
  7 10  2  0
 14  4  1  0
 18 26  1  0
M  CHG  2  18   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4556137

   ---

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: 374.47

Molecular Weight (Monoisotopic): 374.1413

AlogP: 0.91

#Rotatable Bonds: 3

Polar Surface Area: 84.52

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.99

CX Basic pKa: 2.24

CX LogP: -0.40

CX LogD: -0.49

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.80

Np Likeness Score: -1.12

References

1. Shirai F, Tsumura T, Yashiroda Y, Yuki H, Niwa H, Sato S, Chikada T, Koda Y, Washizuka K, Yoshimoto N, Abe M, Onuki T, Mazaki Y, Hirama C, Fukami T, Watanabe H, Honma T, Umehara T, Shirouzu M, Okue M, Kano Y, Watanabe T, Kitamura K, Shitara E, Muramatsu Y, Yoshida H, Mizutani A, Seimiya H, Yoshida M, Koyama H..  (2019)  Discovery of Novel Spiroindoline Derivatives as Selective Tankyrase Inhibitors.,  62  (7): [PMID:30883102] [10.1021/acs.jmedchem.8b01888]

Source

Source(1):

• Scientific Literature