(S)-N-(3-amino-1-cyano-3-oxopropyl)-3-((3'-fluoro-[1,1'-biphenyl]-4-yl)sulphonyl)-2,2-dimethylpropanamide

ID: ALA4549828

PubChem CID: 155550740

Max Phase: Preclinical

Molecular Formula: C21H22FN3O4S

Molecular Weight: 431.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(CS(=O)(=O)c1ccc(-c2cccc(F)c2)cc1)C(=O)N[C@H](C#N)CC(N)=O

Standard InChI:  InChI=1S/C21H22FN3O4S/c1-21(2,20(27)25-17(12-23)11-19(24)26)13-30(28,29)18-8-6-14(7-9-18)15-4-3-5-16(22)10-15/h3-10,17H,11,13H2,1-2H3,(H2,24,26)(H,25,27)/t17-/m0/s1

Standard InChI Key:  HVCVCOKHVNDIKN-KRWDZBQOSA-N

Molfile:  

 
     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
   19.9964   -1.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1681   -1.0153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5808   -1.7252    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.9892   -1.0128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3490   -3.3760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3478   -4.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0559   -4.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7655   -4.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7627   -3.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0541   -2.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4658   -2.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1754   -3.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8810   -2.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8784   -2.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1642   -1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4614   -2.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2938   -2.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7092   -2.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7114   -2.9476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4158   -1.7199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1246   -2.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9922   -0.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7022   -1.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8312   -1.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5327   -1.3044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1269   -2.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8357   -3.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8379   -4.1676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5423   -2.9398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6411   -2.9676    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  4  3  2  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  9 11  1  0
 14  3  1  0
  3 17  1  0
 17  1  1  0
  1 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
  1 22  1  0
  1 23  1  0
 21 24  1  0
 24 25  3  0
 21 26  1  6
 26 27  1  0
 27 28  1  0
 27 29  2  0
  5 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4549828

   ---

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: 431.49

Molecular Weight (Monoisotopic): 431.1315

AlogP: 2.18

#Rotatable Bonds: 8

Polar Surface Area: 130.12

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.33

CX Basic pKa: ┄

CX LogP: 1.64

CX LogD: 1.64

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.66

Np Likeness Score: -1.15

References

1. Eddie SL, Gregson A, Graham E, Burton S, Harrison T, Burden R, Scott CJ, Mullan PB, Williams R..  (2019)  Identification and SAR exploration of a novel series of Legumain inhibitors.,  29  (12): [PMID:31005445] [10.1016/j.bmcl.2019.03.019]

Source

Source(1):

• Scientific Literature