2-(4-(2-(4-(2,2-dimethylbutyl)-1H-imidazol-2-yl)ethyl)phenyl)-5-fluoropyridine

ID: ALA1093184

PubChem CID: 25025861

Max Phase: Preclinical

Molecular Formula: C22H26FN3

Molecular Weight: 351.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C)(C)Cc1c[nH]c(CCc2ccc(-c3ccc(F)cn3)cc2)n1

Standard InChI:  InChI=1S/C22H26FN3/c1-4-22(2,3)13-19-15-25-21(26-19)12-7-16-5-8-17(9-6-16)20-11-10-18(23)14-24-20/h5-6,8-11,14-15H,4,7,12-13H2,1-3H3,(H,25,26)

Standard InChI Key:  KYTBMJJCUATLFE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -1.7556  -13.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7568  -14.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0419  -14.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3255  -14.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3284  -13.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0437  -12.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4696  -14.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1841  -14.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8984  -14.5985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8995  -15.4244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1803  -15.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4689  -15.4237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3846  -12.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1006  -13.3534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8135  -12.9383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5659  -13.2740    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1156  -12.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7004  -11.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8941  -12.1205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9406  -12.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3493  -11.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1743  -11.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5830  -11.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5208  -11.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5583  -11.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6137  -15.8373    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0
  5 13  1  0
  1  2  2  0
 13 14  1  0
  3  4  2  0
 14 15  1  0
 15 16  2  0
  7  8  2  0
  8  9  1  0
  4  5  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 15  1  0
  9 10  2  0
 17 20  1  0
  2  3  1  0
 20 21  1  0
 10 11  1  0
 21 22  1  0
  5  6  2  0
 22 23  1  0
 11 12  2  0
 21 24  1  0
 12  7  1  0
 21 25  1  0
  2  7  1  0
 10 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1093184

   2-(4-(2-(4-(2,2-dimethylbutyl)-1H-imidazol-2-yl)ethyl)phenyl)-5-fluoropyridine

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: 351.47

Molecular Weight (Monoisotopic): 351.2111

AlogP: 5.37

#Rotatable Bonds: 7

Polar Surface Area: 41.57

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.14

CX LogP: 5.52

CX LogD: 5.34

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.62

Np Likeness Score: -0.97

References

1. Liu J, He S, Jian T, Dobbelaar PH, Sebhat IK, Lin LS, Goodman A, Guo C, Guzzo PR, Hadden M, Henderson AJ, Pattamana K, Ruenz M, Sargent BJ, Swenson B, Yet L, Tamvakopoulos C, Peng Q, Pan J, Kan Y, Palyha O, Kelly TM, Guan XM, Howard AD, Marsh DJ, Metzger JM, Reitman ML, Wyvratt MJ, Nargund RP..  (2010)  Synthesis and SAR of derivatives based on 2-biarylethylimidazole as bombesin receptor subtype-3 (BRS-3) agonists for the treatment of obesity.,  20  (7): [PMID:20219372] [10.1016/j.bmcl.2010.02.076]

2. Sebhat IK, Franklin C, Lo MM, Chen D, Jewell JP, Miller R, Pang J, Palyha O, Kan Y, Kelly TM, Guan XM, Marsh DJ, Kosinski JA, Metzger JM, Lyons K, Dragovic J, Guzzo PR, Henderson AJ, Reitman ML, Nargund RP, Wyvratt MJ, Lin LS..  (2011)  Discovery of MK-5046, a Potent, Selective Bombesin Receptor Subtype-3 Agonist for the Treatment of Obesity.,  2  (1): [PMID:24900253] [10.1021/ml100196d]

Source

Source(1):

• Scientific Literature