(S)-2-(1-acryloylpiperidin-2-yl)-1-amino-4-(4-((4-bromopyridin-2-yl)carbamoyl)phenyl)-1H-imidazole-5-carboxamide

ID: ALA4878421

PubChem CID: 155307528

Max Phase: Preclinical

Molecular Formula: C24H24BrN7O3

Molecular Weight: 538.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC(=O)N1CCCC[C@H]1c1nc(-c2ccc(C(=O)Nc3cc(Br)ccn3)cc2)c(C(N)=O)n1N

Standard InChI:  InChI=1S/C24H24BrN7O3/c1-2-19(33)31-12-4-3-5-17(31)23-30-20(21(22(26)34)32(23)27)14-6-8-15(9-7-14)24(35)29-18-13-16(25)10-11-28-18/h2,6-11,13,17H,1,3-5,12,27H2,(H2,26,34)(H,28,29,35)/t17-/m0/s1

Standard InChI Key:  FNNWNXFWBPLQIV-KRWDZBQOSA-N

Molfile:  

 
     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
   21.6454  -11.9103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4665  -11.8243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6379  -11.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9193  -10.6028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3066  -11.1600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3910  -10.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0605  -11.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8153  -10.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9019  -10.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2277   -9.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4758   -9.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6544   -9.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7826   -8.8708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2912  -10.1999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.0603   -9.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7022  -10.4312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4719  -10.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5978   -9.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9521   -8.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1887   -9.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5005  -10.9876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8324   -9.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4995   -9.2981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0797   -9.4465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4711  -13.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8803  -14.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7062  -14.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8812  -12.6251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6476  -13.3397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2316  -12.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4091  -12.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9962  -13.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4079  -14.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2367  -14.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0747   -7.9859    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3  6  1  0
  9 12  1  0
 12 13  2  0
 12 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 15  1  0
  5 21  1  0
  4 22  1  0
 22 23  1  0
 22 24  2  0
 30  1  1  1
 29 25  1  0
 25 26  1  0
 26 27  2  0
 25 28  2  0
 29 30  1  0
 29 34  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 19 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4878421

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 538.41

Molecular Weight (Monoisotopic): 537.1124

AlogP: 3.01

#Rotatable Bonds: 6

Polar Surface Area: 149.23

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 2.62

CX LogP: 2.64

CX LogD: 2.64

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.32

Np Likeness Score: -1.01

References

1. Ma C, Li Q, Zhao M, Fan G, Zhao J, Zhang D, Yang S, Zhang S, Gao D, Mao L, Zhu L, Li W, Xu G, Jiang Y, Ding Q..  (2021)  Discovery of 1-Amino-1H-imidazole-5-carboxamide Derivatives as Highly Selective, Covalent Bruton's Tyrosine Kinase (BTK) Inhibitors.,  64  (21.0): [PMID:34672559] [10.1021/acs.jmedchem.1c01559]

Source

Source(1):

• Scientific Literature