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

ID: ALA4237919

PubChem CID: 131985494

Max Phase: Preclinical

Molecular Formula: C27H34N6O2

Molecular Weight: 474.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nncn1-c1cccc([C@H](CC(=O)O)CN2CC[C@@H](CCc3ccc4c(n3)NCCC4)C2)c1

Standard InChI:  InChI=1S/C27H34N6O2/c1-19-31-29-18-33(19)25-6-2-4-22(14-25)23(15-26(34)35)17-32-13-11-20(16-32)7-9-24-10-8-21-5-3-12-28-27(21)30-24/h2,4,6,8,10,14,18,20,23H,3,5,7,9,11-13,15-17H2,1H3,(H,28,30)(H,34,35)/t20-,23-/m1/s1

Standard InChI Key:  DRMIWPCMCBXOEN-NFBKMPQASA-N

Molfile:  

     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
   16.1680  -25.6023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9531  -25.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4132  -25.1537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9102  -24.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1435  -24.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3100  -24.7908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0197  -24.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.6061  -23.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9023  -23.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1899  -23.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1858  -24.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8941  -24.7903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7280  -24.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.4773  -25.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2743  -26.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9079  -26.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7247  -26.4661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5216  -27.2118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4570  -26.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0709  -27.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5015  -27.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3224  -27.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7049  -27.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7594  -28.6464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4533  -29.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0793  -29.9293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7724  -29.4963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5746  -28.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6604  -29.6017    0.0000 C   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
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 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
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 30  1  0
 28 30  1  0
 31 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4237919

   ---

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: 474.61

Molecular Weight (Monoisotopic): 474.2743

AlogP: 3.84

#Rotatable Bonds: 9

Polar Surface Area: 96.17

Molecular Species: ZWITTERION

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.95

CX Basic pKa: 10.28

CX LogP: -0.14

CX LogD: -0.36

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.49

Np Likeness Score: -0.71

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]

Source

Source(1):

• Scientific Literature