2-(2-sec-butyl-3-oxo-2,3-dihydroimidazo[1,2-c]quinazolin-5-ylthio)-N-o-tolylbutanamide

ID: ALA4212457

Cas Number: 1052659-30-9

PubChem CID: 20965633

Max Phase: Preclinical

Molecular Formula: C25H28N4O2S

Molecular Weight: 448.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(SC1=Nc2ccccc2C2=NC(C(C)CC)C(=O)N12)C(=O)Nc1ccccc1C

Standard InChI:  InChI=1S/C25H28N4O2S/c1-5-15(3)21-24(31)29-22(28-21)17-12-8-10-14-19(17)27-25(29)32-20(6-2)23(30)26-18-13-9-7-11-16(18)4/h7-15,20-21H,5-6H2,1-4H3,(H,26,30)

Standard InChI Key:  HTFJGDBBWXQQCN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.8055  -12.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5155  -13.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5155  -11.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2256  -12.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6457  -12.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9356  -11.6288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3516  -11.6288    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.3516  -10.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6457  -10.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9356  -10.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0617  -10.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0617   -9.5786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6457  -12.8557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9356  -13.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1051  -14.0688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9199  -14.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2514  -13.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0529  -13.2357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3275  -14.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9199  -15.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1467  -14.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5584  -14.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7697  -10.8058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7694   -9.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4727   -9.5815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1799   -9.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1803   -8.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4676   -7.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7633   -8.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4701  -10.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  8  1  0
  6 16  1  0
 15  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
 19 20  2  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 13 25  2  0
 14 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 27 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4212457

   2-((2-(sec-butyl)-3-oxo-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)thio)-N-(o-tolyl)butanamide

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: 448.59

Molecular Weight (Monoisotopic): 448.1933

AlogP: 5.15

#Rotatable Bonds: 6

Polar Surface Area: 74.13

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.13

CX Basic pKa: 1.98

CX LogP: 6.31

CX LogD: 6.31

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.66

Np Likeness Score: -0.96

References

1. Yang SM, Martinez NJ, Yasgar A, Danchik C, Johansson C, Wang Y, Baljinnyam B, Wang AQ, Xu X, Shah P, Cheff D, Wang XS, Roth J, Lal-Nag M, Dunford JE, Oppermann U, Vasiliou V, Simeonov A, Jadhav A, Maloney DJ..  (2018)  Discovery of Orally Bioavailable, Quinoline-Based Aldehyde Dehydrogenase 1A1 (ALDH1A1) Inhibitors with Potent Cellular Activity.,  61  (11): [PMID:29767973] [10.1021/acs.jmedchem.8b00270]

2. Li B, Yang K, Liang D, Jiang C, Ma Z..  (2021)  Discovery and development of selective aldehyde dehydrogenase 1A1 (ALDH1A1) inhibitors.,  209  [PMID:33328099] [10.1016/j.ejmech.2020.112940]

Source

Source(1):

• Scientific Literature