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

ID: ALA4776138

PubChem CID: 162643332

Max Phase: Preclinical

Molecular Formula: C24H27Br2N3O3

Molecular Weight: 565.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)C[C@H](C(=O)N1CC[C@@H](CCc2ccc3c(n2)NCCC3)C1)c1cc(Br)cc(Br)c1

Standard InChI:  InChI=1S/C24H27Br2N3O3/c25-18-10-17(11-19(26)12-18)21(13-22(30)31)24(32)29-9-7-15(14-29)3-5-20-6-4-16-2-1-8-27-23(16)28-20/h4,6,10-12,15,21H,1-3,5,7-9,13-14H2,(H,27,28)(H,30,31)/t15-,21+/m1/s1

Standard InChI Key:  NSLLXYFCBUUZFG-VFNWGFHPSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   12.6788  -23.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6788  -24.3754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3841  -24.7799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3841  -23.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0894  -23.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0859  -24.3754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7880  -24.7847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4980  -24.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5015  -23.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7949  -23.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2034  -24.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9134  -24.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6188  -24.8019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6963  -25.6112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4946  -25.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9072  -25.0802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3638  -24.4699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7204  -24.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1971  -25.6630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0569  -24.2546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8606  -26.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0103  -25.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0477  -26.4855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7112  -27.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1880  -27.8941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0051  -27.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3379  -27.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4869  -26.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3001  -26.1650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1504  -26.9906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4833  -28.4690    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   17.8976  -27.3052    0.0000 Br  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
  8  9  1  0
  9 10  2  0
  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
 17 13  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  1
 19 22  1  0
 21 23  2  0
 23 24  1  0
 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
 26 31  1  0
 24 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4776138

   ---

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: 565.31

Molecular Weight (Monoisotopic): 563.0419

AlogP: 5.00

#Rotatable Bonds: 7

Polar Surface Area: 82.53

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.13

CX Basic pKa: 7.52

CX LogP: 2.28

CX LogD: 2.04

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.49

Np Likeness Score: -0.32

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