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

ID: ALA4468875

PubChem CID: 155533172

Max Phase: Preclinical

Molecular Formula: C23H24ClN5O3

Molecular Weight: 453.93

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)CC(Nc1ncc(OCCc2ccc3c(n2)NCCC3)cn1)c1ccc(Cl)cc1

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

Standard InChI Key:  KAMSHMVKMNHYHX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   30.2817  -26.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9981  -26.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9953  -25.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2799  -24.7944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5669  -26.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5665  -25.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8537  -24.7961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1368  -25.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1372  -26.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8545  -26.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7081  -24.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4242  -25.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1370  -24.7830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8530  -25.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8530  -26.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5682  -26.4263    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.2820  -26.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2762  -25.1818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5605  -24.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9985  -26.4199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.7108  -26.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4274  -26.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1397  -25.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8563  -26.4054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.1355  -25.1715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.7066  -25.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4206  -24.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4168  -23.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6996  -23.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9850  -23.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9924  -24.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6944  -22.7061    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:

   

   ALA4468875

   ---

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: 3.62

CX Basic pKa: 7.18

CX LogP: 1.36

CX LogD: 0.96

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.44

Np Likeness Score: -0.59

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