(3S)-3-(3-(3,5-Dimethyl-1H-pyrazol-1-yl)phenyl)-4-((1S,3R)-1-methyl-3-(2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl)pyrrolidin-1-ium-1-yl)butanoate

ID: ALA4468357

PubChem CID: 139030528

Product Number: S609430, Order Now?

Max Phase: Preclinical

Molecular Formula: C30H39N5O2

Molecular Weight: 501.68

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(C)n(-c2cccc([C@H](CC(=O)[O-])C[N@@+]3(C)CC[C@@H](CCc4ccc5c(n4)NCCC5)C3)c2)n1

Standard InChI:  InChI=1S/C30H39N5O2/c1-21-16-22(2)34(33-21)28-8-4-6-25(17-28)26(18-29(36)37)20-35(3)15-13-23(19-35)9-11-27-12-10-24-7-5-14-31-30(24)32-27/h4,6,8,10,12,16-17,23,26H,5,7,9,11,13-15,18-20H2,1-3H3,(H-,31,32,36,37)/t23-,26-,35+/m1/s1

Standard InChI Key:  BXOSGYRJKCYDLH-YAYCEGLDSA-N

Molfile:  

 
     RDKit          2D

 37 41  0  0  0  0  0  0  0  0999 V2000
   22.5718   -2.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8661   -2.7033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5764   -3.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7386   -2.4377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4482   -2.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4454   -1.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7368   -0.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0305   -2.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0346   -1.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3308   -0.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6184   -1.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6143   -2.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3226   -2.4373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1566   -2.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8636   -2.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5720   -2.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6613   -3.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4609   -3.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3206   -2.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5809   -3.9254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2909   -4.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2954   -5.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0054   -5.5518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5900   -5.5597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8755   -4.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1667   -3.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4617   -4.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4658   -5.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1808   -5.5637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8828   -5.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1912   -6.3789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5345   -6.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7940   -7.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6113   -7.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8566   -6.8533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7550   -6.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0976   -8.2894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  8  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  9  1  0
  8  9  2  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  5 14  1  0
 14 15  1  0
 16 15  1  1
 16 17  1  0
 17 18  1  0
 18  2  1  0
  2 19  1  0
 19 16  1  0
  3 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 20 25  1  1
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 31  1  0
 29 31  1  0
 32 36  1  0
 34 37  1  0
M  CHG  2   2   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4468357

   (3S)-3-(3-(3,5-Dimethyl-1H-pyrazol-1-yl)phenyl)-4-((1S,3R)-1-methyl-3-(2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl)pyrrolidin-1-ium-1-yl)butanoate

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: 501.68

Molecular Weight (Monoisotopic): 501.3104

AlogP: 3.57

#Rotatable Bonds: 9

Polar Surface Area: 82.87

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.27

CX Basic pKa: 7.51

CX LogP: -0.68

CX LogD: 0.36

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.45

Np Likeness Score: -0.72

References

1. 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