methyl (R)-3-((4-(3-aminopiperidin-1-yl)-3-(but-2-yn-1-yl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)methyl)-5-bromobenzoate

ID: ALA4863369

PubChem CID: 164622612

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(Cc2cc(Br)cc(C(=O)OC)c2)c1=O

Standard InChI:  InChI=1S/C22H25BrN4O4/c1-3-4-8-26-19(25-7-5-6-18(24)14-25)12-20(28)27(22(26)30)13-15-9-16(21(29)31-2)11-17(23)10-15/h9-12,18H,5-8,13-14,24H2,1-2H3/t18-/m1/s1

Standard InChI Key:  KIHKGIDJKYCFHB-GOSISDBHSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   21.0103   -9.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0092  -10.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7172  -11.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4269  -10.6418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4240   -9.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7154   -9.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1302   -9.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8394   -9.8138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8399  -10.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5451  -11.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2537  -10.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2526   -9.8127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5429   -9.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9614  -11.0394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9582  -11.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6618  -12.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3719  -11.8620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3739  -11.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6658  -10.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5408   -8.5851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1326  -11.0421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9601   -9.4038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9598   -8.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9596   -7.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9593   -6.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0830  -10.6377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3025   -9.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3023   -8.5971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5949   -9.8231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8871   -9.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7170  -11.8685    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
  3 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4863369

   ---

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: -0.77

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