Rac-3-(4-Chlorophenyl)-3-((5-(2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy)pyrazin-2-yl)amino)propanoic Acid

ID: ALA4483501

PubChem CID: 155540544

Max Phase: Preclinical

Molecular Formula: C23H24ClN5O3

Molecular Weight: 453.93

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)CC(Nc1cnc(OCCc2ccc3c(n2)NCCC3)cn1)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C23H24ClN5O3/c24-17-6-3-15(4-7-17)19(12-22(30)31)29-20-13-27-21(14-26-20)32-11-9-18-8-5-16-2-1-10-25-23(16)28-18/h3-8,13-14,19H,1-2,9-12H2,(H,25,28)(H,26,29)(H,30,31)

Standard InChI Key:  GLKYDNKLZWQQCW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   17.0614   -4.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7779   -4.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7751   -3.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0596   -3.0871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3467   -4.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3463   -3.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6335   -3.0887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9165   -3.5005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9169   -4.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6343   -4.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4879   -3.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2039   -3.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9167   -3.0756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6328   -3.4854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6328   -4.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3479   -4.7190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0617   -4.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0560   -3.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3402   -3.0685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7783   -4.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4906   -4.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2072   -4.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9195   -4.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6360   -4.6980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9152   -3.4642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4864   -3.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2004   -3.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1966   -2.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4794   -1.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7648   -2.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7721   -3.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4741   -0.9988    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 21 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483501

   ---

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: 453.93

Molecular Weight (Monoisotopic): 453.1568

AlogP: 4.13

#Rotatable Bonds: 9

Polar Surface Area: 109.26

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.55

CX Basic pKa: 7.18

CX LogP: 1.36

CX LogD: 0.95

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.44

Np Likeness Score: -0.70

References

1. Anderson NA, Campos S, Butler S, Copley RCB, Duncan I, Harrison S, Le J, Maghames R, Pastor-Garcia A, Pritchard JM, Rowedder JE, Smith CE, Thomas J, Vitulli G, Macdonald SJF..  (2019)  Discovery of an Orally Bioavailable Pan αv Integrin Inhibitor for Idiopathic Pulmonary Fibrosis.,  62  (19): [PMID:31497959] [10.1021/acs.jmedchem.9b00962]

Source

Source(1):

• Scientific Literature