4-(6-(benzofuran-5-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-N-(2,2,2-trifluoroethyl)thiophene-2-carboxamide

ID: ALA4526375

PubChem CID: 155544039

Max Phase: Preclinical

Molecular Formula: C21H13F3N4O2S

Molecular Weight: 442.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NCC(F)(F)F)c1cc(-c2cnn3cc(-c4ccc5ccoc5c4)cnc23)cs1

Standard InChI:  InChI=1S/C21H13F3N4O2S/c22-21(23,24)11-26-20(29)18-6-14(10-31-18)16-8-27-28-9-15(7-25-19(16)28)13-2-1-12-3-4-30-17(12)5-13/h1-10H,11H2,(H,26,29)

Standard InChI Key:  FQTQQQOXDGYLJS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   17.4087   -4.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1139   -5.0022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1139   -3.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8192   -3.7805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8192   -4.5987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5973   -4.8517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0784   -4.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5974   -3.5278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8515   -5.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3711   -6.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8514   -6.9553    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   20.6286   -5.8856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2898   -7.1831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2043   -7.9958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0363   -6.8507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6974   -7.3311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4440   -6.9987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1051   -7.4790    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.5294   -6.1860    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   24.1484   -6.5829    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.7021   -3.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7011   -2.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9930   -2.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9992   -3.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2906   -3.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2866   -2.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5067   -2.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0286   -2.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5131   -3.6402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1 23  1  0
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 30 31  1  0
 31 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4526375

   ---

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: 442.42

Molecular Weight (Monoisotopic): 442.0711

AlogP: 5.16

#Rotatable Bonds: 4

Polar Surface Area: 72.43

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.90

CX Basic pKa: 0.98

CX LogP: 4.05

CX LogD: 4.05

Aromatic Rings: 5

Heavy Atoms: 31

QED Weighted: 0.42

Np Likeness Score: -1.41

References

1. Sloman DL, Noucti N, Altman MD, Chen D, Mislak AC, Szewczak A, Hayashi M, Warren L, Dellovade T, Wu Z, Marcus J, Walker D, Su HP, Edavettal SC, Munshi S, Hutton M, Nuthall H, Stanton MG..  (2016)  Optimization of microtubule affinity regulating kinase (MARK) inhibitors with improved physical properties.,  26  (17): [PMID:27491711] [10.1016/j.bmcl.2016.02.003]

Source

Source(1):

• Scientific Literature