1-(3,4-Dimethoxyphenyl)-1-(3-fluorobenzyl)-3-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea

ID: ALA4539841

PubChem CID: 155549874

Max Phase: Preclinical

Molecular Formula: C23H27FN4O2S

Molecular Weight: 442.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(N(Cc2cccc(F)c2)C(=S)NCCCn2cncc2C)cc1OC

Standard InChI:  InChI=1S/C23H27FN4O2S/c1-17-14-25-16-27(17)11-5-10-26-23(31)28(15-18-6-4-7-19(24)12-18)20-8-9-21(29-2)22(13-20)30-3/h4,6-9,12-14,16H,5,10-11,15H2,1-3H3,(H,26,31)

Standard InChI Key:  MKJUKNYEJIRNNS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   22.2836   -9.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2825  -10.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9905  -10.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7002  -10.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6974   -9.5133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9887   -9.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4035   -9.1020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4085  -10.7434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5745  -10.7445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8671  -10.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1590  -10.7433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4517  -10.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7436  -10.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0362  -10.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3282  -10.7411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5808  -10.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0335  -11.0175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4416  -11.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2410  -11.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8476  -12.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8677   -9.5181    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.1128   -9.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1156  -10.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5738  -11.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2812  -11.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2754  -12.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9819  -13.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6909  -12.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6890  -11.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9818  -11.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9809  -14.0135    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  4  8  1  0
  2  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 15  1  0
 19 20  1  0
 10 21  2  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 27 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4539841

   ---

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: 442.56

Molecular Weight (Monoisotopic): 442.1839

AlogP: 4.32

#Rotatable Bonds: 9

Polar Surface Area: 51.55

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.25

CX Basic pKa: 7.33

CX LogP: 3.57

CX LogD: 3.39

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.39

Np Likeness Score: -1.88

References

1. 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]

Source

Source(1):

• Scientific Literature