(2S)-2-[(biphenyl-4-ylsulfonyl)amino]-5-(ethylamino)-5-oxopentanoic acid

ID: ALA3828315

PubChem CID: 127045131

Max Phase: Preclinical

Molecular Formula: C19H22N2O5S

Molecular Weight: 390.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNC(=O)CC[C@H](NS(=O)(=O)c1ccc(-c2ccccc2)cc1)C(=O)O

Standard InChI:  InChI=1S/C19H22N2O5S/c1-2-20-18(22)13-12-17(19(23)24)21-27(25,26)16-10-8-15(9-11-16)14-6-4-3-5-7-14/h3-11,17,21H,2,12-13H2,1H3,(H,20,22)(H,23,24)/t17-/m0/s1

Standard InChI Key:  NAPWKGYKWPYSDL-KRWDZBQOSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   -5.1975    2.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8995    3.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9005    5.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2002    6.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2012    7.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1954    1.7981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2380    3.5960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1621    8.1040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5998    3.0012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5988    1.5004    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8991   -0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1969   -1.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945   -3.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8943   -3.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5965   -3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5009    8.2541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6383    2.0999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6378    0.9001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5019    9.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5411   10.3549    0.0000 C   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
  1  6  2  0
  1  7  1  0
  5  8  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
 11 17  1  0
 10 14  1  0
  9 10  1  0
  2  9  1  6
  5 23  1  0
 10 24  2  0
 10 25  2  0
 23 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3828315

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 390.46

Molecular Weight (Monoisotopic): 390.1249

AlogP: 2.00

#Rotatable Bonds: 9

Polar Surface Area: 112.57

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.37

CX Basic pKa: ┄

CX LogP: 1.92

CX LogD: -1.49

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.61

Np Likeness Score: -0.86

References

1. Adhikari N, Halder AK, Mallick S, Saha A, Saha KD, Jha T..  (2016)  Robust design of some selective matrix metalloproteinase-2 inhibitors over matrix metalloproteinase-9 through in silico/fragment-based lead identification and de novo lead modification: Syntheses and biological assays.,  24  (18): [PMID:27452283] [10.1016/j.bmc.2016.07.023]

Source

Source(1):

• Scientific Literature