(S)-3-(3-Bromophenyl)-4-((R)-3-(2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)butanoic Acid

ID: ALA4242175

PubChem CID: 145985939

Max Phase: Preclinical

Molecular Formula: C24H30BrN3O2

Molecular Weight: 472.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C[C@H](CN1CC[C@@H](CCc2ccc3c(n2)NCCC3)C1)c1cccc(Br)c1

Standard InChI:  InChI=1S/C24H30BrN3O2/c25-21-5-1-3-19(13-21)20(14-23(29)30)16-28-12-10-17(15-28)6-8-22-9-7-18-4-2-11-26-24(18)27-22/h1,3,5,7,9,13,17,20H,2,4,6,8,10-12,14-16H2,(H,26,27)(H,29,30)/t17-,20-/m1/s1

Standard InChI Key:  QZTBJCSOVXRYCX-YLJYHZDGSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    6.0728   -3.2492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8579   -3.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3180   -2.8007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8150   -2.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0483   -2.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2148   -2.4377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9245   -2.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9217   -1.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2130   -0.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5068   -2.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5109   -1.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8071   -0.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0947   -1.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0906   -2.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7989   -2.4373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6328   -2.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -2.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1348   -2.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5653   -3.4696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3821   -3.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1791   -4.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8127   -4.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6295   -4.1130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4264   -4.8588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3618   -4.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9757   -4.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4063   -5.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2272   -5.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6097   -4.8805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6602   -6.2933    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
 10  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 11  1  0
 10 11  2  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  7 16  1  0
 16 17  1  0
  5 17  1  1
  3 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  1
 20 22  1  0
 22 23  1  0
 22 24  2  0
 21 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 21  1  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4242175

   ---

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: 472.43

Molecular Weight (Monoisotopic): 471.1521

AlogP: 4.72

#Rotatable Bonds: 8

Polar Surface Area: 65.46

Molecular Species: ZWITTERION

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.45

CX Basic pKa: 9.13

CX LogP: 1.66

CX LogD: 1.49

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.58

Np Likeness Score: -0.34

References

1. Procopiou PA, Anderson NA, Barrett J, Barrett TN, Crawford MHJ, Fallon BJ, Hancock AP, Le J, Lemma S, Marshall RP, Morrell J, Pritchard JM, Rowedder JE, Saklatvala P, Slack RJ, Sollis SL, Suckling CJ, Thorp LR, Vitulli G, Macdonald SJF..  (2018)  Discovery of ( S)-3-(3-(3,5-Dimethyl-1 H-pyrazol-1-yl)phenyl)-4-(( R)-3-(2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)butanoic Acid, a Nonpeptidic αvβ6 Integrin Inhibitor for the Inhaled Treatment of Idiopathic Pulmonary Fibrosis.,  61  (18): [PMID:30215258] [10.1021/acs.jmedchem.8b00959]

2. Lippa RA,Barrett J,Pal S,Rowedder JE,Murphy JA,Barrett TN.  (2020)  Discovery of the first potent and selective αβ integrin inhibitor based on an amide-containing core.,  208  [PMID:32865176] [10.1016/j.ejmech.2020.112719]

Source

Source(1):

• Scientific Literature