N-(2-naphthylsulfonyl)-glycyl-glycine-nitrile

ID: ALA200338

PubChem CID: 11652399

Max Phase: Preclinical

Molecular Formula: C14H13N3O3S

Molecular Weight: 303.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CCNC(=O)CNS(=O)(=O)c1ccc2ccccc2c1

Standard InChI:  InChI=1S/C14H13N3O3S/c15-7-8-16-14(18)10-17-21(19,20)13-6-5-11-3-1-2-4-12(11)9-13/h1-6,9,17H,8,10H2,(H,16,18)

Standard InChI Key:  LVYWXNHSBUSHNC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   11.9882  -11.0841    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7026  -10.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4172  -11.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1318  -10.6716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4172  -11.9092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8463  -11.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5608  -10.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2788  -10.2624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2736  -10.6716    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.6853   -9.9565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8651  -11.3884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5591  -10.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5619   -9.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1354  -10.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8496  -10.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1327   -9.4331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8474   -9.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8469   -8.1978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1324   -7.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4169   -8.2029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4209   -9.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  2  0
  4  6  1  0
  9 12  1  0
  1  2  1  0
 12 13  2  0
 13 17  1  0
  6  7  1  0
 16 14  1  0
  3  4  1  0
 14 15  2  0
 15 12  1  0
  7  8  3  0
 16 17  1  0
  1  9  1  0
 17 18  2  0
  3  5  2  0
 18 19  1  0
  9 10  2  0
 19 20  2  0
  2  3  1  0
 20 21  1  0
 21 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA200338

   N-(cyanomethyl)-2-(naphthalene-2-sulfonamido)acetamide

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: 303.34

Molecular Weight (Monoisotopic): 303.0678

AlogP: 0.76

#Rotatable Bonds: 5

Polar Surface Area: 99.06

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.03

CX Basic pKa: ┄

CX LogP: 0.22

CX LogD: 0.22

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.80

Np Likeness Score: -1.95

References

1. Löser R, Schilling K, Dimmig E, Gütschow M..  (2005)  Interaction of papain-like cysteine proteases with dipeptide-derived nitriles.,  48  (24): [PMID:16302809] [10.1021/jm050686b]

Source

Source(1):

• Scientific Literature