6-(4-hydroxy-3-methoxybenzylidene)-5-imino-2-(trifluoromethyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7(6H)-one

ID: ALA4787157

PubChem CID: 16411419

Max Phase: Preclinical

Molecular Formula: C14H9F3N4O3S

Molecular Weight: 370.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C2/C(=N)N3N=C(C(F)(F)F)SC3=NC2=O)ccc1O

Standard InChI:  InChI=1S/C14H9F3N4O3S/c1-24-9-5-6(2-3-8(9)22)4-7-10(18)21-13(19-11(7)23)25-12(20-21)14(15,16)17/h2-5,18,22H,1H3/b7-4-,18-10?

Standard InChI Key:  CQYCTLSWCZSZBJ-HMUYFDHHSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    7.3067   -8.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3056   -9.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0204  -10.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7368   -9.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7340   -8.9962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0186   -8.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5922   -8.5874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5920   -7.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5909  -10.2390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4468   -8.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1629   -8.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1634   -9.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8752  -10.2227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8730   -8.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5895   -8.9851    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5937   -9.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3770  -10.0574    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.8569   -9.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3701   -8.7270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8690   -7.7458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4494  -10.2261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6819   -9.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0981  -10.0978    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.0907   -8.6689    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.5039   -9.3831    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  7  8  1  0
  2  9  1  0
  5 10  1  0
 10 11  2  0
 11 12  1  0
 11 14  1  0
 12 13  1  0
 13 16  2  0
 15 14  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 15  1  0
 14 20  2  0
 12 21  2  0
 18 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4787157

   Srpin803

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: 370.31

Molecular Weight (Monoisotopic): 370.0347

AlogP: 2.58

#Rotatable Bonds: 2

Polar Surface Area: 98.34

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.37

CX Basic pKa: ┄

CX LogP: 2.64

CX LogD: 2.64

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.78

Np Likeness Score: -1.08

References

1. Dalle Vedove A,Zonta F,Zanforlin E,Demitri N,Ribaudo G,Cazzanelli G,Ongaro A,Sarno S,Zagotto G,Battistutta R,Ruzzene M,Lolli G.  (2020)  A novel class of selective CK2 inhibitors targeting its open hinge conformation.,  195  [PMID:32283296] [10.1016/j.ejmech.2020.112267]

2. Tang J, Xie Y, Huang J, Zhang L, Jiang W, Li Z, Bian J..  (2022)  A critical update on the strategies towards small molecule inhibitors targeting Serine/arginine-rich (SR) proteins and Serine/arginine-rich proteins related kinases in alternative splicing.,  70  [PMID:35863237] [10.1016/j.bmc.2022.116921]

Source

Source(1):

• Scientific Literature