1-(4-(4-(2-Aminopyridin-4-yl)butoxy)-3-methoxyphenyl)-3-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea

ID: ALA4097599

Cas Number: 2092921-50-9

PubChem CID: 92045043

Max Phase: Preclinical

Molecular Formula: C24H32N6O2S

Molecular Weight: 468.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(NC(=S)NCCCn2cncc2C)ccc1OCCCCc1ccnc(N)c1

Standard InChI:  InChI=1S/C24H32N6O2S/c1-18-16-26-17-30(18)12-5-10-28-24(33)29-20-7-8-21(22(15-20)31-2)32-13-4-3-6-19-9-11-27-23(25)14-19/h7-9,11,14-17H,3-6,10,12-13H2,1-2H3,(H2,25,27)(H2,28,29,33)

Standard InChI Key:  MXAZSKBTKUGBLI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    0.0982   -4.0849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6530   -3.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1990   -4.3645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7904   -5.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0134   -4.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311   -5.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8053   -3.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5136   -4.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2207   -3.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9291   -4.0803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6361   -3.6706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3445   -4.0781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6348   -2.8534    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0515   -3.6684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7572   -4.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4638   -3.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4629   -2.8520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7496   -2.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0460   -2.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1695   -2.4413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1671   -1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8736   -1.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8712   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1720   -4.0778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1729   -4.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5777    0.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5753    0.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2817    1.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2797    2.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5703    2.4721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8614    2.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8670    1.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1511    2.4584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  1  5  1  0
  5  6  1  0
  1  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 16 24  1  0
 24 25  1  0
 23 26  1  0
 26 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
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4097599

   Glutaminyl Cyclase Inhibitor 3

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: 468.63

Molecular Weight (Monoisotopic): 468.2307

AlogP: 3.96

#Rotatable Bonds: 12

Polar Surface Area: 99.25

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.48

CX Basic pKa: 7.72

CX LogP: 3.29

CX LogD: 2.78

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.27

Np Likeness Score: -1.02

References

1. Hoang VH, Tran PT, Cui M, Ngo VT, Ann J, Park J, Lee J, Choi K, Cho H, Kim H, Ha HJ, Hong HS, Choi S, Kim YH, Lee J..  (2017)  Discovery of Potent Human Glutaminyl Cyclase Inhibitors as Anti-Alzheimer's Agents Based on Rational Design.,  60  (6): [PMID:28234463] [10.1021/acs.jmedchem.7b00098]

2. Hoang VH, Ngo VTH, Cui M, Manh NV, Tran PT, Ann J, Ha HJ, Kim H, Choi K, Kim YH, Chang H, Macalino SJY, Lee J, Choi S, Lee J..  (2019)  Discovery of Conformationally Restricted Human Glutaminyl Cyclase Inhibitors as Potent Anti-Alzheimer's Agents by Structure-Based Design.,  62  (17): [PMID:31411468] [10.1021/acs.jmedchem.9b00751]

3. Van Manh N, Hoang VH, Ngo VTH, Ann J, Jang TH, Ha JH, Song JY, Ha HJ, Kim H, Kim YH, Lee J, Lee J..  (2021)  Discovery of highly potent human glutaminyl cyclase (QC) inhibitors as anti-Alzheimer's agents by the combination of pharmacophore-based and structure-based design.,  226  [PMID:34536669] [10.1016/j.ejmech.2021.113819]

Source

Source(1):

• Scientific Literature