2-(1-Acetylpiperidin-2-yl)-N-(5-((R)-3-((5-(2-phenylacetamido)-1,3,4-thiadiazol-2-yl)amino)pyrrolidin-1-yl)-1,3,4-thiadiazol-2-yl)acetamide

ID: ALA4444363

PubChem CID: 155516989

Max Phase: Preclinical

Molecular Formula: C25H31N9O3S2

Molecular Weight: 569.72

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)N1CCCCC1CC(=O)Nc1nnc(N2CC[C@@H](Nc3nnc(NC(=O)Cc4ccccc4)s3)C2)s1

Standard InChI:  InChI=1S/C25H31N9O3S2/c1-16(35)34-11-6-5-9-19(34)14-21(37)28-24-31-32-25(39-24)33-12-10-18(15-33)26-22-29-30-23(38-22)27-20(36)13-17-7-3-2-4-8-17/h2-4,7-8,18-19H,5-6,9-15H2,1H3,(H,26,29)(H,27,30,36)(H,28,31,37)/t18-,19?/m1/s1

Standard InChI Key:  KMTPUYZKVPSMRS-MRTLOADZSA-N

Molfile:  

 
     RDKit          2D

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   30.1884  -27.1036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4762  -26.6873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.4127  -28.6299    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2384  -28.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6462  -29.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6602  -27.9265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4719  -29.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8716  -30.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   32.8833  -28.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   25.1596  -25.7561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   23.3589  -26.9510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1265  -26.9551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6465  -26.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9278  -26.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6526  -25.7092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2152  -26.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2124  -27.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.5136  -25.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7946  -25.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7885  -26.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5014  -26.9375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4981  -27.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.2108  -28.1779    0.0000 O   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
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  8 10  1  0
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 20 21  1  0
 22 18  1  0
 22 23  1  0
 19 24  1  0
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 25 26  1  0
 25 27  2  0
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 24 29  1  0
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 30 16  1  0
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 28 32  1  0
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 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 37 39  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4444363

   ---

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: 569.72

Molecular Weight (Monoisotopic): 569.1991

AlogP: 2.99

#Rotatable Bonds: 9

Polar Surface Area: 145.34

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 6.79

CX Basic pKa: ┄

CX LogP: 2.17

CX LogD: 1.29

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.35

Np Likeness Score: -1.62

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