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

ID: ALA4207309

PubChem CID: 68378958

Max Phase: Preclinical

Molecular Formula: C24H29N5O

Molecular Weight: 403.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1nn2c(C)cc(C)nc2c1Cc1ccc(/C=C/CN2CCNCC2=O)cc1

Standard InChI:  InChI=1S/C24H29N5O/c1-4-22-21(24-26-17(2)14-18(3)29(24)27-22)15-20-9-7-19(8-10-20)6-5-12-28-13-11-25-16-23(28)30/h5-10,14,25H,4,11-13,15-16H2,1-3H3/b6-5+

Standard InChI Key:  KSZKHAJWBULFPL-AATRIKPKSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    3.5069   -8.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9522   -9.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7785   -9.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1574   -8.6647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8880   -8.0123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7072   -7.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9192   -7.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2310   -6.7300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5938   -7.2466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875   -5.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792   -5.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6828   -8.7843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2247  -10.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3520   -7.1733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3509   -8.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0657   -8.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7821   -8.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7793   -7.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0639   -6.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6375   -6.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4973   -8.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2111   -7.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9262   -8.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6400   -7.9957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3518   -8.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0635   -8.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0651   -7.1764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3515   -6.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6335   -7.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3493   -9.2365    0.0000 O   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  1  0
 24 25  1  0
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 25 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4207309

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

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: 403.53

Molecular Weight (Monoisotopic): 403.2372

AlogP: 2.94

#Rotatable Bonds: 6

Polar Surface Area: 62.53

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.05

CX LogP: 3.02

CX LogD: 2.86

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.69

Np Likeness Score: -0.93

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