(S)-3-(3-Cyanophenyl)-4-oxo-4-((R)-3-(2-(5,6,7,8-tetrahydro1,8-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)butanoic acid

ID: ALA4756062

PubChem CID: 162655518

Max Phase: Preclinical

Molecular Formula: C25H28N4O3

Molecular Weight: 432.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1cccc([C@H](CC(=O)O)C(=O)N2CC[C@@H](CCc3ccc4c(n3)NCCC4)C2)c1

Standard InChI:  InChI=1S/C25H28N4O3/c26-15-18-3-1-4-20(13-18)22(14-23(30)31)25(32)29-12-10-17(16-29)6-8-21-9-7-19-5-2-11-27-24(19)28-21/h1,3-4,7,9,13,17,22H,2,5-6,8,10-12,14,16H2,(H,27,28)(H,30,31)/t17-,22+/m1/s1

Standard InChI Key:  LKLFMSIRSSIJBV-VGSWGCGISA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   13.2484   -1.1804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2484   -1.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9537   -2.4020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9537   -0.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6590   -1.1804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6555   -1.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3576   -2.4069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0676   -2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0710   -1.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3645   -0.7725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7730   -2.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4830   -2.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1884   -2.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2658   -3.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0642   -3.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4768   -2.7023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9333   -2.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2900   -2.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7666   -3.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6265   -1.8767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4301   -4.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5798   -3.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6173   -4.1077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2808   -4.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7576   -5.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5747   -5.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9075   -4.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0565   -3.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8696   -3.7872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7199   -4.6128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0556   -6.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5346   -6.7542    0.0000 N   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
 31 32  3  0
 26 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4756062

   ---

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: 432.52

Molecular Weight (Monoisotopic): 432.2161

AlogP: 3.35

#Rotatable Bonds: 7

Polar Surface Area: 106.32

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.08

CX Basic pKa: 7.52

CX LogP: 0.60

CX LogD: 0.36

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.69

Np Likeness Score: -0.70

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