1-(((3S,4S)-3-(3-fluorophenyl)-4-((4-(2-((4-fluorophenyl)sulfonyl)ethyl)piperidin-1-yl)methyl)pyrrolidin-1-yl)methyl)cyclopentanecarboxylic acid

ID: ALA5280882

Max Phase: Preclinical

Molecular Formula: C31H40F2N2O4S

Molecular Weight: 574.73

Names and Identifiers

Canonical SMILES:  O=C(O)C1(CN2C[C@H](CN3CCC(CCS(=O)(=O)c4ccc(F)cc4)CC3)[C@@H](c3cccc(F)c3)C2)CCCC1

Standard InChI:  InChI=1S/C31H40F2N2O4S/c32-26-6-8-28(9-7-26)40(38,39)17-12-23-10-15-34(16-11-23)19-25-20-35(22-31(30(36)37)13-1-2-14-31)21-29(25)24-4-3-5-27(33)18-24/h3-9,18,23,25,29H,1-2,10-17,19-22H2,(H,36,37)/t25-,29+/m0/s1

Standard InChI Key:  JLKKIAYYHXNZIY-ABYGYWHVSA-N

Molfile:  

 
     RDKit          2D

 40 44  0  0  0  0  0  0  0  0999 V2000
   -2.7385   -0.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4060   -0.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1511    0.6195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3259    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0711   -0.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2740   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6904    0.2046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9040    1.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3205    1.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4765    1.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6901    0.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1066   -0.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5636    1.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3888    1.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8015    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6267    0.6195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3888   -0.0951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2091    1.4203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4223    2.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6664    2.6395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0534    2.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7385   -1.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0239   -1.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0247   -2.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7396   -3.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4515   -2.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4562   -1.8897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3100   -3.1235    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.0600    1.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8571    1.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4406    2.3251    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2377    2.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8215    2.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6159    2.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8296    1.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2500    1.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4522    1.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6267    1.4702    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6546    3.1236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8575    2.9101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  5  6  1  6
  6  7  1  0
  8  7  1  0
  9  8  1  0
 10  9  1  0
 11 10  1  0
 12 11  1  0
  7 12  1  0
  3 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 14 21  1  0
  1 22  1  1
 23 22  2  0
 24 23  1  0
 25 24  2  0
 26 25  1  0
 22 27  1  0
 27 26  2  0
 24 28  1  0
 10 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 33 32  2  0
 34 33  1  0
 35 34  2  0
 36 35  1  0
 37 36  2  0
 32 37  1  0
 35 38  1  0
 31 39  2  0
 31 40  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5280882

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 574.73

Molecular Weight (Monoisotopic): 574.2677

AlogP: 5.20

#Rotatable Bonds: 10

Polar Surface Area: 77.92

Molecular Species: ZWITTERION

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.51

CX Basic pKa: 10.25

CX LogP: 2.18

CX LogD: 2.16

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.39

Np Likeness Score: -0.80

References

1. Gathiaka S, Palte RL, So SS, Chai X, Richard Miller J, Kuvelkar R, Wen X, Cifelli S, Kreamer A, Liaw A, McLaren DG, Fischer C..  (2023)  Discovery of non-boronic acid Arginase 1 inhibitors through virtual screening and biophysical methods.,  84  [PMID:36822300] [10.1016/j.bmcl.2023.129193]

Source

Source(1):

• Scientific Literature