N,N'-(5,5'-(Ethane-1,2-diylbis(azanediyl))bis(1,3,4-thiadiazole-5,2-diyl))bis(2-phenylacetamide)

ID: ALA4461749

PubChem CID: 132002549

Max Phase: Preclinical

Molecular Formula: C22H22N8O2S2

Molecular Weight: 494.61

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Cc1ccccc1)Nc1nnc(NCCNc2nnc(NC(=O)Cc3ccccc3)s2)s1

Standard InChI:  InChI=1S/C22H22N8O2S2/c31-17(13-15-7-3-1-4-8-15)25-21-29-27-19(33-21)23-11-12-24-20-28-30-22(34-20)26-18(32)14-16-9-5-2-6-10-16/h1-10H,11-14H2,(H,23,27)(H,24,28)(H,25,29,31)(H,26,30,32)

Standard InChI Key:  BUYLTKNZNYDIFG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   27.3062  -11.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6396  -12.2004    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.4575  -12.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6339  -11.3182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9253  -10.9041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8570  -12.8364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6782  -12.8445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0840  -13.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0979  -12.1367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9053  -13.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3029  -14.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1234  -14.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5439  -13.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1337  -12.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3145  -12.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0911  -11.5131    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.7582  -11.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5038  -10.2502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6825  -10.2502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4240  -11.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7126  -11.4388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4654  -11.4429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1781  -11.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8891  -11.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0038  -11.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2890  -11.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0100  -10.2036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5802  -11.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5897  -10.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8818   -9.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1659  -10.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1624  -11.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8709  -11.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6017  -11.0384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0
  3  4  2  0
  2  3  1  0
  4  5  1  0
  1  2  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 19 20  2  0
 17 18  2  0
 16 17  1  0
 18 19  1  0
 20 16  1  0
 20 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 21 25  1  0
 25 26  1  0
 25 27  2  0
 26 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
 24 34  1  0
 34  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4461749

   ---

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: 494.61

Molecular Weight (Monoisotopic): 494.1307

AlogP: 3.28

#Rotatable Bonds: 11

Polar Surface Area: 133.82

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.78

CX Basic pKa: 0.08

CX LogP: 3.15

CX LogD: 2.26

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.23

Np Likeness Score: -1.14

References

1. Finlay MRV, Anderton M, Bailey A, Boyd S, Brookfield J, Cairnduff C, Charles M, Cheasty A, Critchlow SE, Culshaw J, Ekwuru T, Hollingsworth I, Jones N, Leroux F, Littleson M, McCarron H, McKelvie J, Mooney L, Nissink JWM, Perkins D, Powell S, Quesada MJ, Raubo P, Sabin V, Smith J, Smith PD, Stark A, Ting A, Wang P, Wilson Z, Winter-Holt JJ, Wood JM, Wrigley GL, Yu G, Zhang P..  (2019)  Discovery of a Thiadiazole-Pyridazine-Based Allosteric Glutaminase 1 Inhibitor Series That Demonstrates Oral Bioavailability and Activity in Tumor Xenograft Models.,  62  (14): [PMID:31199640] [10.1021/acs.jmedchem.9b00260]

Source

Source(1):

• Scientific Literature