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

ID: ALA4875769

PubChem CID: 164625947

Max Phase: Preclinical

Molecular Formula: C21H23BrN4O4

Molecular Weight: 475.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC#CCn1c(N2CCC[C@@H](N)C2)cc(=O)n(Cc2cccc(C(=O)O)c2Br)c1=O

Standard InChI:  InChI=1S/C21H23BrN4O4/c1-2-3-10-25-17(24-9-5-7-15(23)13-24)11-18(27)26(21(25)30)12-14-6-4-8-16(19(14)22)20(28)29/h4,6,8,11,15H,5,7,9-10,12-13,23H2,1H3,(H,28,29)/t15-/m1/s1

Standard InChI Key:  ZVBHZDPQGFCOJI-OAHLLOKOSA-N

Molfile:  

 
     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   11.5796  -20.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5784  -20.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2865  -21.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9961  -20.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9933  -20.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2847  -19.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6995  -19.6063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4087  -20.0122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4092  -20.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1144  -21.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8230  -20.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8219  -20.0111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1122  -19.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5307  -21.2378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5275  -22.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2311  -22.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9412  -22.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9432  -21.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2350  -20.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1101  -18.7835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7019  -21.2404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5294  -19.6022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5291  -18.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5288  -17.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5285  -17.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6523  -20.8360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8718  -19.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8716  -18.7955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1642  -20.0215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2823  -18.7951    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
  6 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4875769

   ---

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: 475.34

Molecular Weight (Monoisotopic): 474.0903

AlogP: 1.47

#Rotatable Bonds: 5

Polar Surface Area: 110.56

Molecular Species: ZWITTERION

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.20

CX Basic pKa: 9.47

CX LogP: 0.53

CX LogD: 0.52

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.63

Np Likeness Score: -0.62

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