N,N'-(5,5'-((1R,3R)-cyclopentane-1,3-diyl)bis(1,3,4-thiadiazole-5,2-diyl))bis(2-(pyridin-2-yl)acetamide)

ID: ALA4556025

PubChem CID: 90163218

Max Phase: Preclinical

Molecular Formula: C23H22N8O2S2

Molecular Weight: 506.62

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Cc1ccccn1)Nc1nnc([C@@H]2CC[C@@H](c3nnc(NC(=O)Cc4ccccn4)s3)C2)s1

Standard InChI:  InChI=1S/C23H22N8O2S2/c32-18(12-16-5-1-3-9-24-16)26-22-30-28-20(34-22)14-7-8-15(11-14)21-29-31-23(35-21)27-19(33)13-17-6-2-4-10-25-17/h1-6,9-10,14-15H,7-8,11-13H2,(H,26,30,32)(H,27,31,33)/t14-,15-/m1/s1

Standard InChI Key:  AGGLFYIKNHWBEV-HUUCEWRRSA-N

Molfile:  

 
     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
   24.5177  -16.3444    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.1807  -15.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9263  -15.0857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1091  -15.0857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8547  -15.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1439  -16.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8860  -16.2743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5939  -15.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3014  -16.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5944  -15.0489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0094  -15.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7143  -16.2799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4218  -15.8724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4227  -15.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7103  -14.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0057  -15.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8222  -16.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1133  -15.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4526  -16.3485    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.8612  -15.0898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0440  -15.0898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7897  -15.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0783  -16.2743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3736  -15.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6629  -16.2637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3798  -15.0432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9583  -15.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9685  -15.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2647  -14.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5530  -15.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5495  -15.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2539  -16.2532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0724  -17.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8896  -17.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4810  -15.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  2  0
  2  3  2  0
  1  2  1  0
  3  4  1  0
  5  1  1  0
  6  5  1  6
  2  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 17 18  1  1
 21 22  2  0
 18 20  2  0
 19 18  1  0
 20 21  1  0
 22 19  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 33 34  1  0
 34  6  1  0
  6 35  1  0
 35 17  1  0
 17 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4556025

   2-pyridin-2-yl-N-[5-[(1R,3R)-3-[5-[(2-pyridin-2-ylacetyl)amino]-1,3,4-thiadiazol-2-yl]cyclopentyl]-1,3,4-thiadiazol-2-yl]acetamide

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: 506.62

Molecular Weight (Monoisotopic): 506.1307

AlogP: 3.59

#Rotatable Bonds: 8

Polar Surface Area: 135.54

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.63

CX Basic pKa: 4.63

CX LogP: 2.71

CX LogD: 1.63

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.37

Np Likeness Score: -1.28

References

1. Zimmermann SC, Duvall B, Tsukamoto T..  (2018)  Recent Progress in the Discovery of Allosteric Inhibitors of Kidney-Type Glutaminase.,  62  (1): [PMID:29969024] [10.1021/acs.jmedchem.8b00327]

Source

Source(1):

• Scientific Literature