(R)-5-((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: ALA4873862

PubChem CID: 164619888

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(Cc2cc(C(=O)O)ccc2Br)c1=O

Standard InChI:  InChI=1S/C21H23BrN4O4/c1-2-3-9-25-18(24-8-4-5-16(23)13-24)11-19(27)26(21(25)30)12-15-10-14(20(28)29)6-7-17(15)22/h6-7,10-11,16H,4-5,8-9,12-13,23H2,1H3,(H,28,29)/t16-/m1/s1

Standard InChI Key:  RUFVCBKABZGJLK-MRXNPFEDSA-N

Molfile:  

 
     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    4.1753  -20.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1742  -21.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8822  -21.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5919  -21.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5891  -20.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8804  -20.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7368  -19.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4461  -20.3837    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4466  -21.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1518  -21.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8603  -21.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8592  -20.3825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1495  -19.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5680  -21.6093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5648  -22.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2685  -22.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9786  -22.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9806  -21.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2724  -21.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1474  -19.1550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7393  -21.6119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5668  -19.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5665  -19.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5662  -18.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5659  -17.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6897  -21.2075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3002  -21.8627    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.4648  -20.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4646  -19.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7572  -20.6379    0.0000 O   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
  4 27  1  0
 28 29  1  0
 28 30  2  0
  1 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4873862

   ---

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: 4.00

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: -0.67

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