4-((((5-(Aminomethyl)-6-isobutyl-2-methyl-4-(4-methylphenyl)pyridin-3-yl)carbonyl)oxy)methyl)benzoic acid dihydrochloride

ID: ALA4100667

PubChem CID: 69446993

Max Phase: Preclinical

Molecular Formula: C27H32Cl2N2O4

Molecular Weight: 446.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(-c2c(CN)c(CC(C)C)nc(C)c2C(=O)OCc2ccc(C(=O)O)cc2)cc1.Cl.Cl

Standard InChI:  InChI=1S/C27H30N2O4.2ClH/c1-16(2)13-23-22(14-28)25(20-9-5-17(3)6-10-20)24(18(4)29-23)27(32)33-15-19-7-11-21(12-8-19)26(30)31;;/h5-12,16H,13-15,28H2,1-4H3,(H,30,31);2*1H

Standard InChI Key:  QETFKWTUKGFJOU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 35  0  0  0  0  0  0  0  0999 V2000
   27.3663  -30.4708    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.9951  -27.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9939  -28.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7065  -28.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7047  -26.9970    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4219  -27.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4227  -28.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7092  -29.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9963  -29.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9980  -30.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7116  -31.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4294  -30.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4243  -29.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7146  -31.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2773  -28.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5613  -28.2362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2787  -26.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2785  -26.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5620  -25.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9947  -25.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1374  -26.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1364  -28.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1396  -29.4640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8471  -28.2279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5609  -28.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2715  -28.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9807  -28.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6892  -28.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6904  -27.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9768  -26.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2621  -27.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4026  -26.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1147  -27.3989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4026  -26.1653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6791  -30.8082    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  4  8  1  0
 11 14  1  0
  3 15  1  0
 15 16  1  0
  2 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
  6 21  1  0
  7 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 26 25  1  0
 26 27  2  0
 26 31  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 29 32  1  0
 32 33  2  0
 32 34  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 446.55

Molecular Weight (Monoisotopic): 446.2206

AlogP: 5.08

#Rotatable Bonds: 8

Polar Surface Area: 102.51

Molecular Species: ZWITTERION

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.20

CX Basic pKa: 9.12

CX LogP: 2.86

CX LogD: 2.85

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.47

Np Likeness Score: -0.35

References

1. Maezaki H, Tawada M, Yamashita T, Banno Y, Miyamoto Y, Yamamoto Y, Ikedo K, Kosaka T, Tsubotani S, Tani A, Asakawa T, Suzuki N, Oi S..  (2017)  Design of potent dipeptidyl peptidase IV (DPP-4) inhibitors by employing a strategy to form a salt bridge with Lys554.,  27  (15): [PMID:28579121] [10.1016/j.bmcl.2017.05.048]

Source

Source(1):

• Scientific Literature