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

ID: ALA4543688

PubChem CID: 155552698

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)c1cccc(Cl)c1

Standard InChI:  InChI=1S/C23H24ClN5O3/c24-17-5-1-3-16(11-17)20(12-21(30)31)29-23-26-13-19(14-27-23)32-10-8-18-7-6-15-4-2-9-25-22(15)28-18/h1,3,5-7,11,13-14,20H,2,4,8-10,12H2,(H,25,28)(H,30,31)(H,26,27,29)

Standard InChI Key:  PJHLFOBDSFTTTO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   31.2853  -11.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0016  -11.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9988  -10.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2834  -10.0907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5704  -11.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5700  -10.5035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8573  -10.0924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1404  -10.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1408  -11.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8581  -11.7471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7117  -10.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4276  -10.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1405  -10.0793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8564  -10.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8564  -11.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5716  -11.7226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.2855  -11.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2796  -10.4781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.5640  -10.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0020  -11.7162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.7143  -11.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4307  -11.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1431  -11.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8596  -11.7016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.1389  -10.4678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.7101  -10.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4240  -10.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4201   -9.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7031   -8.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9884   -9.2480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9957  -10.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1326   -8.8213    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
 28 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4543688

   ---

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: -0.66

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