3-(4-Morpholinophenyl)-4-((pyridin-2-ylmethyl)amino)cyclobut-3-ene-1,2-dione

ID: ALA4101131

PubChem CID: 132277783

Max Phase: Preclinical

Molecular Formula: C20H19N3O3

Molecular Weight: 349.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1c(NCc2ccccn2)c(-c2ccc(N3CCOCC3)cc2)c1=O

Standard InChI:  InChI=1S/C20H19N3O3/c24-19-17(18(20(19)25)22-13-15-3-1-2-8-21-15)14-4-6-16(7-5-14)23-9-11-26-12-10-23/h1-8,22H,9-13H2

Standard InChI Key:  PPDXHFIWMLVDEJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    7.8937  -15.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0741  -15.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0850  -15.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9006  -15.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4638  -16.4804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4879  -16.4585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4868  -14.5085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2748  -14.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8570  -14.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6550  -13.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2412  -12.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0292  -13.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2312  -13.8086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6450  -14.3798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5149  -14.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7230  -14.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1519  -14.1014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3726  -13.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1644  -13.1114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7356  -13.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601  -11.5589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4520  -11.3570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0231  -11.9431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8024  -12.7312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0106  -12.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4394  -12.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  1  4  1  0
  1  5  2  0
  2  6  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  9 14  2  0
  8  9  1  0
  7  8  1  0
  4  7  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 21 26  1  0
 18 24  1  0
  3 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4101131

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 349.39

Molecular Weight (Monoisotopic): 349.1426

AlogP: 1.79

#Rotatable Bonds: 5

Polar Surface Area: 71.53

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.15

CX LogP: 2.22

CX LogD: 2.22

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.71

Np Likeness Score: -1.49

References

1. Tantry SJ, Markad SD, Shinde V, Bhat J, Balakrishnan G, Gupta AK, Ambady A, Raichurkar A, Kedari C, Sharma S, Mudugal NV, Narayan A, Naveen Kumar CN, Nanduri R, Bharath S, Reddy J, Panduga V, Prabhakar KR, Kandaswamy K, Saralaya R, Kaur P, Dinesh N, Guptha S, Rich K, Murray D, Plant H, Preston M, Ashton H, Plant D, Walsh J, Alcock P, Naylor K, Collier M, Whiteaker J, McLaughlin RE, Mallya M, Panda M, Rudrapatna S, Ramachandran V, Shandil R, Sambandamurthy VK, Mdluli K, Cooper CB, Rubin H, Yano T, Iyer P, Narayanan S, Kavanagh S, Mukherjee K, Balasubramanian V, Hosagrahara VP, Solapure S, Ravishankar S, Hameed P S..  (2017)  Discovery of Imidazo[1,2-a]pyridine Ethers and Squaramides as Selective and Potent Inhibitors of Mycobacterial Adenosine Triphosphate (ATP) Synthesis.,  60  (4): [PMID:28075132] [10.1021/acs.jmedchem.6b01358]

2. Li P,Wang B,Li G,Fu L,Zhang D,Lin Z,Huang H,Lu Y.  (2020)  Design, synthesis and biological evaluation of diamino substituted cyclobut-3-ene-1,2-dione derivatives for the treatment of drug-resistant tuberculosis.,  206  [PMID:32927218] [10.1016/j.ejmech.2020.112538]

3. Kumar G, Kapoor S..  (2023)  Targeting mycobacterial membranes and membrane proteins: Progress and limitations.,  81  [PMID:36804747] [10.1016/j.bmc.2023.117212]

Source

Source(1):

• Scientific Literature