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-fluorobenzoate

ID: ALA4846335

PubChem CID: 164609428

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(Cc2ccc(F)c(C(=O)OC)c2)c1=O

Standard InChI:  InChI=1S/C22H25FN4O4/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:  SJNPCVKXNHSFLS-MRXNPFEDSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   11.2824   -3.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2813   -3.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9893   -4.2413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6990   -3.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6962   -3.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9875   -2.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4023   -2.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1116   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1121   -3.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8172   -4.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5258   -3.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5247   -3.0028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8150   -2.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2335   -4.2295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2303   -5.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9339   -5.4571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6441   -5.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6460   -4.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9379   -3.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8129   -1.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4048   -4.2321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2323   -2.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2320   -1.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2317   -0.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2314   -0.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3551   -3.8277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5746   -2.6044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5744   -1.7872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8670   -3.0132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1592   -2.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5732   -4.2404    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
  2 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4846335

   ---

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: -1.06

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