3-(4-((3-(3,5-dichlorophenyl)-5-(4-(trifluoromethoxy)phenyl)-1H-pyrazol-1-yl)methyl)benzamido)propanoic acid

ID: ALA1644183

PubChem CID: 9985625

Max Phase: Preclinical

Molecular Formula: C27H20Cl2F3N3O4

Molecular Weight: 578.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCNC(=O)c1ccc(Cn2nc(-c3cc(Cl)cc(Cl)c3)cc2-c2ccc(OC(F)(F)F)cc2)cc1

Standard InChI:  InChI=1S/C27H20Cl2F3N3O4/c28-20-11-19(12-21(29)13-20)23-14-24(17-5-7-22(8-6-17)39-27(30,31)32)35(34-23)15-16-1-3-18(4-2-16)26(38)33-10-9-25(36)37/h1-8,11-14H,9-10,15H2,(H,33,38)(H,36,37)

Standard InChI Key:  IGCXZPHCSPIQHB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 39 42  0  0  0  0  0  0  0  0999 V2000
   -0.3331   -7.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7498   -8.5778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3431   -9.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4803   -9.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8952   -8.5815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4861   -7.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7202   -8.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1314   -9.2982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1340   -7.8693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9564   -9.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5748   -8.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9918   -9.2844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8133   -9.3620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9900  -10.1679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781  -10.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6616  -10.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7426  -10.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4070  -10.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1622  -10.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2542  -11.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5849  -11.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8323  -11.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8597  -10.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6102  -11.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1949  -11.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7514  -10.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4971   -9.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3074   -9.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5576  -10.7424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8091  -11.5281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6153  -11.7032    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.2544  -12.1388    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.0208  -12.3208    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3676  -10.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8264   -9.8489    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.6734  -12.4689    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.1926  -10.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6065  -10.7331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6091   -9.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
 19 20  2  0
  8 10  1  0
 20 21  1  0
  2  3  1  0
 21 22  2  0
 22 17  1  0
 14 17  1  0
  2 11  1  0
  5  6  2  0
 23 24  2  0
 11 12  1  0
 24 25  1  0
 12 13  1  0
 25 26  2  0
  6  1  1  0
 26 27  1  0
  1  2  2  0
 27 28  2  0
 28 23  1  0
 16 23  1  0
  5  7  1  0
 26 29  1  0
  3  4  2  0
 29 30  1  0
 13 14  2  0
 30 31  1  0
 14 15  1  0
 30 32  1  0
 15 16  2  0
 30 33  1  0
 16 12  1  0
 10 34  1  0
  7  8  1  0
 19 35  1  0
 21 36  1  0
 17 18  2  0
 34 37  1  0
  7  9  2  0
 18 19  1  0
 37 38  1  0
 37 39  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1644183

   3-(4-((3-(3,5-dichlorophenyl)-5-(4-(trifluoromethoxy)phenyl)-1H-pyrazol-1-yl)methyl)benzamido)propanoic 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: 578.37

Molecular Weight (Monoisotopic): 577.0783

AlogP: 6.68

#Rotatable Bonds: 9

Polar Surface Area: 93.45

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.94

CX Basic pKa: 1.90

CX LogP: 7.15

CX LogD: 3.96

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.23

Np Likeness Score: -1.36

References

1. Shen DM, Brady EJ, Candelore MR, Dallas-Yang Q, Ding VD, Feeney WP, Jiang G, McCann ME, Mock S, Qureshi SA, Saperstein R, Shen X, Tong X, Tota LM, Wright MJ, Yang X, Zheng S, Chapman KT, Zhang BB, Tata JR, Parmee ER..  (2011)  Discovery of novel, potent, selective, and orally active human glucagon receptor antagonists containing a pyrazole core.,  21  (1): [PMID:21147532] [10.1016/j.bmcl.2010.11.074]

2. Xiong Y, Guo J, Candelore MR, Liang R, Miller C, Dallas-Yang Q, Jiang G, McCann PE, Qureshi SA, Tong X, Xu SS, Shang J, Vincent SH, Tota LM, Wright MJ, Yang X, Zhang BB, Tata JR, Parmee ER..  (2012)  Discovery of a novel glucagon receptor antagonist N-[(4-{(1S)-1-[3-(3, 5-dichlorophenyl)-5-(6-methoxynaphthalen-2-yl)-1H-pyrazol-1-yl]ethyl}phenyl)carbonyl]-β-alanine (MK-0893) for the treatment of type II diabetes.,  55  (13): [PMID:22708876] [10.1021/jm300579z]

Source

Source(1):

• Scientific Literature