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

ID: ALA4588580

PubChem CID: 155567527

Max Phase: Preclinical

Molecular Formula: C24H25ClN4O3

Molecular Weight: 452.94

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)CC(Nc1ccc(OCCc2ccc3c(n2)NCCC3)cn1)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C24H25ClN4O3/c25-18-6-3-16(4-7-18)21(14-23(30)31)29-22-10-9-20(15-27-22)32-13-11-19-8-5-17-2-1-12-26-24(17)28-19/h3-10,15,21H,1-2,11-14H2,(H,26,28)(H,27,29)(H,30,31)

Standard InChI Key:  CLZGDNHRVKJUHQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    4.4703  -26.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1868  -26.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1839  -25.2993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4686  -24.8903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7556  -26.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7552  -25.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0424  -24.8919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3255  -25.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3259  -26.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0433  -26.5467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8968  -24.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6128  -25.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3256  -24.8788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0417  -25.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0417  -26.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7568  -26.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4706  -26.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4649  -25.2776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7491  -24.8717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1872  -26.5157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8995  -26.0996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6160  -26.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3283  -26.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0449  -26.5012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3242  -25.2673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8953  -25.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6093  -24.8608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6054  -24.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8883  -23.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1736  -24.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1810  -24.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8830  -22.8020    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:

   

   ALA4588580

   ---

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: 452.94

Molecular Weight (Monoisotopic): 452.1615

AlogP: 4.74

#Rotatable Bonds: 9

Polar Surface Area: 96.37

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.76

CX Basic pKa: 7.35

CX LogP: 1.91

CX LogD: 1.83

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.43

Np Likeness Score: -0.71

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