(5-((4-(4-Chlorophenyl)piperidin-1-yl)sulfonyl)picolinoyl)glycine

ID: ALA5278336

Max Phase: Preclinical

Molecular Formula: C19H20ClN3O5S

Molecular Weight: 437.91

Names and Identifiers

Canonical SMILES:  O=C(O)CNC(=O)c1ccc(S(=O)(=O)N2CCC(c3ccc(Cl)cc3)CC2)cn1

Standard InChI:  InChI=1S/C19H20ClN3O5S/c20-15-3-1-13(2-4-15)14-7-9-23(10-8-14)29(27,28)16-5-6-17(21-11-16)19(26)22-12-18(24)25/h1-6,11,14H,7-10,12H2,(H,22,26)(H,24,25)

Standard InChI Key:  HIWYRXWPCQHOSO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   17.2972  -17.4788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6439  -18.0360    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.9533  -17.4516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3524  -18.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3512  -19.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0593  -19.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7689  -19.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7661  -18.4409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0575  -18.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4773  -19.6711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4786  -20.4883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1843  -19.2614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8927  -19.6689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5998  -19.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3081  -19.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5985  -18.4420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9369  -18.4449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2314  -18.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5266  -18.4377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5230  -19.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2304  -19.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9414  -19.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8183  -19.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1116  -19.2480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4031  -19.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4002  -20.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1117  -20.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8172  -20.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6918  -20.8793    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  7 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
  4  2  1  0
  2 17  1  0
 17 18  1  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 20 23  1  0
 26 29  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA5278336

   ---

2. Parent:

   

   ALA5278336

   ---

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: 437.91

Molecular Weight (Monoisotopic): 437.0812

AlogP: 2.12

#Rotatable Bonds: 6

Polar Surface Area: 116.67

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.32

CX Basic pKa: ┄

CX LogP: 1.62

CX LogD: -1.89

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.71

Np Likeness Score: -1.55

References

1. Mann MK, Zepeda-Velázquez CA, González-Álvarez H, Dong A, Kiyota T, Aman AM, Loppnau P, Li Y, Wilson B, Arrowsmith CH, Al-Awar R, Harding RJ, Schapira M..  (2021)  Structure-Activity Relationship of USP5 Inhibitors.,  64  (20.0): [PMID:34648286] [10.1021/acs.jmedchem.1c00889]

Source

Source(1):

• Scientific Literature