4'-(2-(5-butyl-1H-imidazol-2-yl)-5-hydroxypentyl)biphenyl-2-carboxylic acid

ID: ALA1079517

PubChem CID: 46882011

Max Phase: Preclinical

Molecular Formula: C25H30N2O3

Molecular Weight: 406.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCc1cnc(C(CCCO)Cc2ccc(-c3ccccc3C(=O)O)cc2)[nH]1

Standard InChI:  InChI=1S/C25H30N2O3/c1-2-3-8-21-17-26-24(27-21)20(7-6-15-28)16-18-11-13-19(14-12-18)22-9-4-5-10-23(22)25(29)30/h4-5,9-14,17,20,28H,2-3,6-8,15-16H2,1H3,(H,26,27)(H,29,30)

Standard InChI Key:  IZKNYADXWAWXCN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   -5.7764   -0.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7776   -0.9273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0628   -1.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3463   -0.9269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3492   -0.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0646    0.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6393    0.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9230   -0.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2106    0.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2133    1.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9343    1.5560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6438    1.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6301   -1.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6288   -2.1633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9163   -0.9246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5009    1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7843    1.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0720    1.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7801    0.3287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0636   -0.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0594   -0.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6572   -1.3140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6789    1.2363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2278    1.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8114    2.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0056    2.3888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2202    3.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0452    3.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4540    4.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2790    4.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 15  2  0
  4 13  1  0
  7  8  2  0
 10 16  1  0
 16 17  1  0
  8  9  1  0
 17 18  1  0
  4  5  1  0
 17 19  1  0
  9 10  2  0
 19 20  1  0
  2  3  1  0
 20 21  1  0
 10 11  1  0
 21 22  1  0
 18 23  2  0
  5  6  2  0
 11 12  2  0
 12  7  1  0
  5  7  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 18  1  0
  6  1  1  0
 25 27  1  0
  1  2  2  0
 27 28  1  0
  3  4  2  0
 28 29  1  0
 13 14  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1079517

   2-[4-[2-(5-butyl-1H-imidazol-2-yl)-5-hydroxypentyl]phenyl]benzoic acid

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: 406.53

Molecular Weight (Monoisotopic): 406.2256

AlogP: 5.22

#Rotatable Bonds: 11

Polar Surface Area: 86.21

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.68

CX Basic pKa: 7.58

CX LogP: 3.86

CX LogD: 3.65

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.41

Np Likeness Score: 0.11

References

1. He S, Dobbelaar PH, Liu J, Jian T, Sebhat IK, Lin LS, Goodman A, Guo C, Guzzo PR, Hadden M, Henderson AJ, Ruenz M, Sargent BJ, Yet L, Kelly TM, Palyha O, Kan Y, Pan J, Chen H, Marsh DJ, Shearman LP, Strack AM, Metzger JM, Feighner SD, Tan C, Howard AD, Tamvakopoulos C, Peng Q, Guan XM, Reitman ML, Patchett AA, Wyvratt MJ, Nargund RP..  (2010)  Discovery of substituted biphenyl imidazoles as potent, bioavailable bombesin receptor subtype-3 agonists.,  20  (6): [PMID:20167483] [10.1016/j.bmcl.2010.01.154]

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