2-[4-[2-(Oxazolo[4,5-b]pyridin-2-ylthio)ethyl]piperazin-1-yl]-N-(2,4-bis(methylthio)-6-methyl-3-pyridyl)acetamide

ID: ALA4291768

Cas Number: 217094-22-9

PubChem CID: 22272658

Max Phase: Preclinical

Molecular Formula: C22H28N6O2S3

Molecular Weight: 504.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1cc(C)nc(SC)c1NC(=O)CN1CCN(CCSc2nc3ncccc3o2)CC1

Standard InChI:  InChI=1S/C22H28N6O2S3/c1-15-13-17(31-2)19(21(24-15)32-3)25-18(29)14-28-9-7-27(8-10-28)11-12-33-22-26-20-16(30-22)5-4-6-23-20/h4-6,13H,7-12,14H2,1-3H3,(H,25,29)

Standard InChI Key:  XYHAZQCTATWYDN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   30.3585   -3.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3573   -4.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0654   -4.4890    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.0636   -2.8516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7722   -3.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7770   -4.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5614   -4.3299    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.0414   -3.6610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5536   -2.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8586   -3.6562    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   34.2714   -4.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0885   -4.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5013   -5.0619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.0929   -5.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5022   -6.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3197   -6.4710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.7263   -5.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3154   -5.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7298   -7.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5470   -7.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9571   -7.8829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.9541   -6.4675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.5500   -8.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7345   -8.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3275   -9.2977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.7376  -10.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5591  -10.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9624   -9.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3315  -10.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3260   -7.8822    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   35.5088   -7.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7795   -9.2872    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   39.1930   -9.9920    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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26 29  1  0
 24 30  1  0
 30 31  1  0
 28 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4291768

   1-Piperazineacetamide, N-(6-methyl-2,4-bis(methylthio)-3-pyridinyl)-4-(2-(oxazolo(4,5-b)pyridin-2-ylthio)ethyl)-

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: 504.71

Molecular Weight (Monoisotopic): 504.1436

AlogP: 3.72

#Rotatable Bonds: 9

Polar Surface Area: 87.39

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.10

CX Basic pKa: 6.55

CX LogP: 3.02

CX LogD: 2.97

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.44

Np Likeness Score: -1.98

References

1. Shibuya K, Kawamine K, Ozaki C, Ohgiya T, Edano T, Yoshinaka Y, Tsunenari Y..  (2018)  Discovery of Clinical Candidate 2-(4-(2-((1 H-Benzo[ d]imidazol-2-yl)thio)ethyl)piperazin-1-yl)- N-(6-methyl-2,4-bis(methylthio)pyridin-3-yl)acetamide Hydrochloride [K-604], an Aqueous-Soluble Acyl-CoA:Cholesterol O-Acyltransferase-1 Inhibitor.,  61  (23): [PMID:30433781] [10.1021/acs.jmedchem.8b01256]

Source

Source(1):

• Scientific Literature