2-(4-((2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenyl)-5-(piperazin-1-yl)-1,3,4-oxadiazole

ID: ALA4204864

PubChem CID: 145977076

Max Phase: Preclinical

Molecular Formula: C23H27N7O

Molecular Weight: 417.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1nn2c(C)cc(C)nc2c1Cc1ccc(-c2nnc(N3CCNCC3)o2)cc1

Standard InChI:  InChI=1S/C23H27N7O/c1-4-20-19(21-25-15(2)13-16(3)30(21)28-20)14-17-5-7-18(8-6-17)22-26-27-23(31-22)29-11-9-24-10-12-29/h5-8,13,24H,4,9-12,14H2,1-3H3

Standard InChI Key:  UHVOBMKJCCINOK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    7.4159  -11.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8570  -11.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6754  -11.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0508  -11.1597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7934  -10.5135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6048  -10.4706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8149   -9.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1331   -9.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5019   -9.7550    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0900   -8.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7752   -7.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5996  -11.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1174  -12.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2341   -9.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2330  -10.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9410  -10.9109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6507  -10.5015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6478   -9.6788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9392   -9.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5263   -9.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4142  -10.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6268  -11.5794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4430  -11.6212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7349  -10.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0991  -10.3445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5229  -10.6446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1008  -11.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8869  -11.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1015  -10.2251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5236   -9.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7311   -9.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  8 10  1  0
 10 11  1  0
  1 12  1  0
  3 13  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 14 20  1  0
 20  7  1  0
 17 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 21  1  0
 26 27  1  0
 26 31  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4204864

   ---

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: 417.52

Molecular Weight (Monoisotopic): 417.2277

AlogP: 2.96

#Rotatable Bonds: 5

Polar Surface Area: 84.38

Molecular Species: BASE

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.59

CX LogP: 3.17

CX LogD: 1.96

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.53

Np Likeness Score: -1.49

References

1. Velcicky J, Miltz W, Oberhauser B, Orain D, Vaupel A, Weigand K, Dawson King J, Littlewood-Evans A, Nash M, Feifel R, Loetscher P..  (2017)  Development of Selective, Orally Active GPR4 Antagonists with Modulatory Effects on Nociception, Inflammation, and Angiogenesis.,  60  (9): [PMID:28445047] [10.1021/acs.jmedchem.6b01703]

Source

Source(1):

• Scientific Literature