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

ID: ALA4871141

PubChem CID: 164618992

Max Phase: Preclinical

Molecular Formula: C22H25FN4O4

Molecular Weight: 428.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC#CCn1c(N2CCC[C@@H](N)C2)cc(=O)n(Cc2cccc(C(=O)OC)c2F)c1=O

Standard InChI:  InChI=1S/C22H25FN4O4/c1-3-4-11-26-18(25-10-6-8-16(24)14-25)12-19(28)27(22(26)30)13-15-7-5-9-17(20(15)23)21(29)31-2/h5,7,9,12,16H,6,8,10-11,13-14,24H2,1-2H3/t16-/m1/s1

Standard InChI Key:  UFFQXMBSLZWFQG-MRXNPFEDSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    2.4378   -3.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4366   -3.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1447   -4.3198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8543   -3.9103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8515   -3.0877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1429   -2.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5577   -2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2669   -3.0823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2674   -3.9013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9726   -4.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6812   -3.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6800   -3.0812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9703   -2.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3889   -4.3079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3857   -5.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0893   -5.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7994   -5.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8014   -4.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0932   -3.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9683   -1.8536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5601   -4.3105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3876   -2.6723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3873   -1.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3870   -1.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3867   -0.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5105   -3.9061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7300   -2.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7298   -1.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0224   -3.0916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3146   -2.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1404   -1.8652    0.0000 F   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
  6 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4871141

   ---

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: 428.46

Molecular Weight (Monoisotopic): 428.1860

AlogP: 0.93

#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: 2.51

CX LogD: 0.49

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.56

Np Likeness Score: -0.84

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