ethyl 2-(3-(5-((8-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)methylthio)-1,3,4-thiadiazol-2-yl)ureido)benzoate

ID: ALA4558108

PubChem CID: 50802229

Max Phase: Preclinical

Molecular Formula: C22H20N6O4S2

Molecular Weight: 496.57

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1ccccc1NC(=O)Nc1nnc(SCc2cc(=O)n3ccc(C)cc3n2)s1

Standard InChI:  InChI=1S/C22H20N6O4S2/c1-3-32-19(30)15-6-4-5-7-16(15)24-20(31)25-21-26-27-22(34-21)33-12-14-11-18(29)28-9-8-13(2)10-17(28)23-14/h4-11H,3,12H2,1-2H3,(H2,24,25,26,31)

Standard InChI Key:  CEYSWICROJSAGN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   14.6656   -7.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3737   -7.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0833   -7.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0805   -6.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3719   -6.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7917   -7.6526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   17.4975   -6.4257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9141   -7.2407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6586   -7.5689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2045   -6.9608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7948   -6.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9957   -6.4249    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   22.4142   -3.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7887   -4.0194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1162   -3.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9302   -3.1865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2607   -2.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7783   -1.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9616   -1.8693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6348   -2.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2266   -3.7560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4771   -1.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3735   -8.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6656   -8.8802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0811   -8.8805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9580   -8.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2502   -8.8798    0.0000 C   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
  4  7  1  0
  7  8  1  0
  8  9  1  0
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  9 11  1  0
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 20 23  1  0
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 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 20 28  2  0
 26 29  1  0
  3 30  1  0
 30 31  1  0
 30 32  2  0
 31 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4558108

   Ethyl 2-[({5-[({8-methyl-4-oxo-4H-pyrido[1,2-A]pyrimidin-2-YL}methyl)sulfanyl]-1,3,4-thiadiazol-2-YL}carbamoyl)amino]benzoate

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: 496.57

Molecular Weight (Monoisotopic): 496.0987

AlogP: 3.97

#Rotatable Bonds: 7

Polar Surface Area: 127.58

Molecular Species: ACID

HBA: 10

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.37

CX Basic pKa: 0.91

CX LogP: 4.10

CX LogD: 3.21

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.22

Np Likeness Score: -2.54

References

1. Subramanian G, Zhu Y, Bowen SJ, Roush N, White JA, Huczek D, Zachary T, Javens C, Williams T, Janssen A, Gonzales A..  (2019)  Lead identification and characterization of hTrkA type 2 inhibitors.,  29  (22): [PMID:31610943] [10.1016/j.bmcl.2019.126680]

Source

Source(1):

• Scientific Literature