(S)-4-((R)-3-(2-(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)-ethyl)pyrrolidin-1-yl)-3-(3-(((R)-tetrahydrofuran-3-yl)oxy)-phenyl)butanoic Acid

ID: ALA4239085

Chembl Id: CHEMBL4239085

PubChem CID: 130454091

Max Phase: Preclinical

Molecular Formula: C28H37N3O4

Molecular Weight: 479.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C[C@H](CN1CC[C@@H](CCc2ccc3c(n2)NCCC3)C1)c1cccc(O[C@@H]2CCOC2)c1

Standard InChI:  InChI=1S/C28H37N3O4/c32-27(33)16-23(22-3-1-5-25(15-22)35-26-11-14-34-19-26)18-31-13-10-20(17-31)6-8-24-9-7-21-4-2-12-29-28(21)30-24/h1,3,5,7,9,15,20,23,26H,2,4,6,8,10-14,16-19H2,(H,29,30)(H,32,33)/t20-,23-,26-/m1/s1

Standard InChI Key:  RZAGOFCCJINLJO-ROSOWXQZSA-N

Alternative Forms

1. Parent:

   

   ALA4239085

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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: 479.62

Molecular Weight (Monoisotopic): 479.2784

AlogP: 4.12

#Rotatable Bonds: 10

Polar Surface Area: 83.92

Molecular Species: ZWITTERION

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.88

CX Basic pKa: 9.98

CX LogP: 0.67

CX LogD: 0.46

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.53

Np Likeness Score: -0.11

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]

2. Barrett TN, Taylor JA, Barker D, Procopiou PA, Thompson JDF, Barrett J, Le J, Lynn SM, Pogany P, Pratley C, Pritchard JM, Roper JA, Rowedder JE, Slack RJ, Vitulli G, Macdonald SJF, Kerr WJ..  (2019)  Profile of a Highly Selective Quaternized Pyrrolidine Betaine α_vβ₆ Integrin Inhibitor-(3S)-3-(3-(3,5-Dimethyl-1H-pyrazol-1-yl)phenyl)-4-((1S and 1R,3R)-1-methyl-3-(2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl)pyrrolidin-1-ium-1-yl)butanoate Synthesized by Stereoselective Methylation.,  62  (16): [PMID:31381331] [10.1021/acs.jmedchem.9b00819]

Source

Source(1):

• Scientific Literature