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

ID: ALA4239588

PubChem CID: 132561360

Max Phase: Preclinical

Molecular Formula: C29H37N5O2

Molecular Weight: 487.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C)n(-c2cccc([C@@H](CC(=O)O)CN3CC[C@@H](CCc4ccc5c(n4)NCCC5)C3)c2)n1

Standard InChI:  InChI=1S/C29H37N5O2/c1-20-15-21(2)34(32-20)27-7-3-5-24(16-27)25(17-28(35)36)19-33-14-12-22(18-33)8-10-26-11-9-23-6-4-13-30-29(23)31-26/h3,5,7,9,11,15-16,22,25H,4,6,8,10,12-14,17-19H2,1-2H3,(H,30,31)(H,35,36)/t22-,25+/m1/s1

Standard InChI Key:  ZMXBIIQMSGOIRZ-RDGATRHJSA-N

Molfile:  

     RDKit          2D

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    8.0036  -16.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.6151  -19.1679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5505  -18.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1643  -19.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5949  -19.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.5467  -21.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.8658  -21.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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  7 16  1  0
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  5 17  1  1
  3 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  6
 20 22  1  0
 22 23  1  0
 22 24  2  0
 21 25  2  0
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 29 21  1  0
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 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 30  1  0
 33 35  1  0
 31 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4239588

   ---

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: 487.65

Molecular Weight (Monoisotopic): 487.2947

AlogP: 4.76

#Rotatable Bonds: 9

Polar Surface Area: 83.28

Molecular Species: ZWITTERION

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.02

CX Basic pKa: 10.26

CX LogP: 1.35

CX LogD: 1.13

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.45

Np Likeness Score: -1.00

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