US8748435, 40

ID: ALA3675746

Cas Number: 1197879-16-5

PubChem CID: 57970302

Max Phase: Preclinical

Molecular Formula: C27H37N5

Molecular Weight: 431.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1nc2c(C)cc(C)nc2n1Cc1ccc(/C=C/CN2CCN(C(C)C)CC2)cc1

Standard InChI:  InChI=1S/C27H37N5/c1-6-25-29-26-21(4)18-22(5)28-27(26)32(25)19-24-11-9-23(10-12-24)8-7-13-30-14-16-31(17-15-30)20(2)3/h7-12,18,20H,6,13-17,19H2,1-5H3/b8-7+

Standard InChI Key:  UAMIBPKKKLTAKG-BQYQJAHWSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    3.7551   -4.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5551   -4.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383    1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.9665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6890   -4.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2234   -5.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2234   -6.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7552   -8.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130   -8.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844   -9.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6539  -10.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1253  -11.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5948  -11.8188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0680  -13.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5373  -13.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5334  -12.4227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0603  -10.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5910  -10.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0042  -12.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7998  -11.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3847  -13.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7131   -7.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2449   -5.8157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12  5  1  0
 12 13  1  0
 13  3  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 22  1  0
 25 28  1  0
 28 29  1  0
 28 30  1  0
 18 31  1  0
 31 32  2  0
 32 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3675746

   GPR4 antagonist 1

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: 431.63

Molecular Weight (Monoisotopic): 431.3049

AlogP: 4.70

#Rotatable Bonds: 7

Polar Surface Area: 37.19

Molecular Species: BASE

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.51

CX LogP: 5.00

CX LogD: 3.86

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.54

Np Likeness Score: -1.50

References

1.  (2014)  Pyrazolo pyrimidine derivatives, 

2. Miltz W, Velcicky J, Dawson J, Littlewood-Evans A, Ludwig MG, Seuwen K, Feifel R, Oberhauser B, Meyer A, Gabriel D, Nash M, Loetscher P..  (2017)  Design and synthesis of potent and orally active GPR4 antagonists with modulatory effects on nociception, inflammation, and angiogenesis.,  25  (16): [PMID:28689977] [10.1016/j.bmc.2017.06.050]

3. 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(2):

• Scientific Literature
• BindingDB Database