methyl(R)-3-((4-(3-aminopiperidin-1-yl)-3-(but-2-yn-1-yl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)methyl)-4-bromobenzoate

ID: ALA4851477

PubChem CID: 164617857

Max Phase: Preclinical

Molecular Formula: C22H25BrN4O4

Molecular Weight: 489.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC#CCn1c(N2CCC[C@@H](N)C2)cc(=O)n(Cc2ccc(Br)c(C(=O)OC)c2)c1=O

Standard InChI:  InChI=1S/C22H25BrN4O4/c1-3-4-10-26-19(25-9-5-6-16(24)14-25)12-20(28)27(22(26)30)13-15-7-8-18(23)17(11-15)21(29)31-2/h7-8,11-12,16H,5-6,9-10,13-14,24H2,1-2H3/t16-/m1/s1

Standard InChI Key:  YQEQJFRNJAHUTF-MRXNPFEDSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   11.8313   -9.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8302   -9.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5382  -10.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2479   -9.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2451   -9.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5365   -8.7370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9512   -8.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6605   -9.1370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6610   -9.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3662  -10.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0747   -9.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0736   -9.1358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3639   -8.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7824  -10.3626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7792  -11.1817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4829  -11.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1930  -11.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1950  -10.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4868   -9.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3618   -7.9083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9537  -10.3652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7812   -8.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7809   -7.9098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7806   -7.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7803   -6.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9041   -9.9608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1235   -8.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1233   -7.9203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4159   -9.1462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7081   -8.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1222  -10.3735    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  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 13  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 13 20  2  0
  9 21  2  0
 12 22  1  0
 22 23  1  0
 23 24  3  0
 24 25  1  0
 18 26  1  6
  1 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
  2 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4851477

   ---

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: 489.37

Molecular Weight (Monoisotopic): 488.1059

AlogP: 1.56

#Rotatable Bonds: 5

Polar Surface Area: 99.56

Molecular Species: BASE

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.47

CX LogP: 3.14

CX LogD: 1.11

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.51

Np Likeness Score: -0.83

References

1. Li Q, Deng X, Jiang N, Meng L, Xing J, Jiang W, Xu Y..  (2021)  Identification and structure-activity relationship exploration of uracil-based benzoic acid and ester derivatives as novel dipeptidyl Peptidase-4 inhibitors for the treatment of type 2 diabetes mellitus.,  225  [PMID:34399391] [10.1016/j.ejmech.2021.113765]

Source

Source(1):

• Scientific Literature