(S)-3-(3,5-Dimethylphenyl)-4-oxo-4-((R)-3-(2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)butanoic acid

ID: ALA4776531

PubChem CID: 162643453

Max Phase: Preclinical

Molecular Formula: C26H33N3O3

Molecular Weight: 435.57

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(C)cc([C@H](CC(=O)O)C(=O)N2CC[C@@H](CCc3ccc4c(n3)NCCC4)C2)c1

Standard InChI:  InChI=1S/C26H33N3O3/c1-17-12-18(2)14-21(13-17)23(15-24(30)31)26(32)29-11-9-19(16-29)5-7-22-8-6-20-4-3-10-27-25(20)28-22/h6,8,12-14,19,23H,3-5,7,9-11,15-16H2,1-2H3,(H,27,28)(H,30,31)/t19-,23+/m1/s1

Standard InChI Key:  AXIJMLLLPVCDAY-XXBNENTESA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   26.5422  -23.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5422  -24.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2475  -25.1513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2475  -23.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.9493  -24.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6514  -25.1562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3614  -24.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3649  -23.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6583  -23.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0668  -25.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7768  -24.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4822  -25.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5596  -25.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3580  -26.1571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7706  -25.4516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.2272  -24.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   34.0604  -26.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9203  -24.6260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.7239  -26.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8736  -25.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9111  -26.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5746  -27.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0514  -28.2655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8685  -28.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2013  -27.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3503  -26.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1634  -26.5364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0138  -27.3620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7613  -27.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3475  -28.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  5 10  1  0
  6  7  1  0
  7  8  2  0
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  8 11  1  0
 11 12  1  0
 13 12  1  1
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
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 16 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  1
 19 22  1  0
 21 23  2  0
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 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 21  1  0
 22 28  1  0
 28 29  1  0
 28 30  2  0
 24 31  1  0
 26 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4776531

   ---

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: 435.57

Molecular Weight (Monoisotopic): 435.2522

AlogP: 4.10

#Rotatable Bonds: 7

Polar Surface Area: 82.53

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.63

CX Basic pKa: 7.52

CX LogP: 1.83

CX LogD: 1.61

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.68

Np Likeness Score: -0.31

References

1. Lippa RA,Barrett J,Pal S,Rowedder JE,Murphy JA,Barrett TN.  (2020)  Discovery of the first potent and selective αβ integrin inhibitor based on an amide-containing core.,  208  [PMID:32865176] [10.1016/j.ejmech.2020.112719]

Source

Source(1):

• Scientific Literature