4-[4-(2-Adamantylcarbamoyl)-5-tert-butyl-pyrazol-1-yl]-benzoic Acid

ID: ALA2177609

Cas Number: 1048668-70-7

PubChem CID: 25006684

Product Number: A650446, Order Now?

Max Phase: Preclinical

Molecular Formula: C25H31N3O3

Molecular Weight: 421.54

Molecule Type: Small molecule

Names and Identifiers

Synonyms: AZD-8329 | AZD8329|1048668-70-7|AZD 8329|AZD-8329|UNII-5B38CV1212|4-[4-(2-Adamantylcarbamoyl)-5-Tert-Butyl-Pyrazol-1-Yl]benzoic Acid|5B38CV1212|CHEMBL2177609|4-(4-(Adamant-2-ylcarbamoyl)-5-tert-butylpyrazol-1-yl)benzoic acid|Benzoic acid, 4-(5-(1,1-dimethylethyl)-4-((tricyclo(3.3.1.13,7)dec-2-ylamino)carbonyl)-1H-pyrazol-1-yl)-|4-[4-(2-adamantylcarbamoyl)-5-tert-butylpyrazol-1-yl]benzoic acid|4-(4-((1r,3r,5r,7r)-adamantan-2-ylcarbamoyl)-5-(tert-butyl)-1H-pyrazol-1-yl)benzoic acid|XWBXJBSVYVJAMZ-Show More⌵

Canonical SMILES:  CC(C)(C)c1c(C(=O)NC2C3CC4CC(C3)CC2C4)cnn1-c1ccc(C(=O)O)cc1

Standard InChI:  InChI=1S/C25H31N3O3/c1-25(2,3)22-20(13-26-28(22)19-6-4-16(5-7-19)24(30)31)23(29)27-21-17-9-14-8-15(11-17)12-18(21)10-14/h4-7,13-15,17-18,21H,8-12H2,1-3H3,(H,27,29)(H,30,31)

Standard InChI Key:  XWBXJBSVYVJAMZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   14.1358  -12.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0730  -11.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7081  -10.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8698  -11.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4128  -11.0883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6154  -11.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1535  -10.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8671  -10.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4184   -9.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7037  -10.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1593  -10.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8398  -12.2373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6570  -12.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9113  -11.4606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2484  -10.9784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5896  -11.4606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3586  -12.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6889  -11.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2954  -11.7568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8599  -10.4100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5456  -12.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0645  -13.4665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3959  -14.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2130  -14.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6904  -13.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9156  -14.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1029  -14.7922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2480  -15.6241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8027  -13.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9486  -12.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5402  -13.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  1  0
  3  5  1  0
  4  6  1  0
  5  7  1  0
  6  7  1  0
  8  9  1  0
  4  8  1  0
  3 10  1  0
  7 11  1  0
 11  9  1  0
  9 10  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 12  1  0
 12 17  1  0
 14 18  1  0
 18 19  1  0
 18 20  2  0
  2 19  1  0
 17 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 17  1  0
 26 27  1  0
 26 28  2  0
 23 26  1  0
 13  1  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2177609

   AZD8329

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: 421.54

Molecular Weight (Monoisotopic): 421.2365

AlogP: 4.42

#Rotatable Bonds: 4

Polar Surface Area: 84.22

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.53

CX Basic pKa: 1.02

CX LogP: 4.43

CX LogD: 1.65

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.77

Np Likeness Score: -1.06

References

1. Scott JS, deSchoolmeester J, Kilgour E, Mayers RM, Packer MJ, Hargreaves D, Gerhardt S, Ogg DJ, Rees A, Selmi N, Stocker A, Swales JG, Whittamore PR..  (2012)  Novel acidic 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitor with reduced acyl glucuronide liability: the discovery of 4-[4-(2-adamantylcarbamoyl)-5-tert-butyl-pyrazol-1-yl]benzoic acid (AZD8329).,  55  (22): [PMID:23088558] [10.1021/jm301252n]

Source

Source(1):

• Scientific Literature