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

ID: ALA3827869

PubChem CID: 59910497

Max Phase: Preclinical

Molecular Formula: C17H18N2O5S

Molecular Weight: 362.41

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H18N2O5S/c18-16(20)11-10-15(17(21)22)19-25(23,24)14-8-6-13(7-9-14)12-4-2-1-3-5-12/h1-9,15,19H,10-11H2,(H2,18,20)(H,21,22)/t15-/m0/s1

Standard InChI Key:  BTMLCSYAKDMZTR-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   -5.1952    3.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1988    1.5012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990    0.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7988    1.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0990    0.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1550    3.6002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2332    3.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1382    1.3524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7508    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
   -9.0994   -0.4476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6377    2.1009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5984    2.7004    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
  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  1
  5 23  1  0
 10 24  2  0
 10 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3827869

   (2S)-5-amino-5-oxo-2-[(4-phenylphenyl)sulfonylamino]pentanoic acid

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: 362.41

Molecular Weight (Monoisotopic): 362.0936

AlogP: 1.35

#Rotatable Bonds: 8

Polar Surface Area: 126.56

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.22

CX Basic pKa: ┄

CX LogP: 1.34

CX LogD: -2.10

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.65

Np Likeness Score: -0.67

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