N-[2-(4-Amino-phenyldisulfanyl)-ethyl]-3-(3-bromo-phenyl)-2-[(E)-hydroxyimino]-propionamide

ID: ALA194868

PubChem CID: 11112984

Max Phase: Preclinical

Molecular Formula: C17H18BrN3O2S2

Molecular Weight: 440.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(SSCCNC(=O)/C(Cc2cccc(Br)c2)=N/O)cc1

Standard InChI:  InChI=1S/C17H18BrN3O2S2/c18-13-3-1-2-12(10-13)11-16(21-23)17(22)20-8-9-24-25-15-6-4-14(19)5-7-15/h1-7,10,23H,8-9,11,19H2,(H,20,22)/b21-16+

Standard InChI Key:  LQAPVRIUQJMQLD-LTGZKZEYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    0.8917   -7.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042   -6.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792   -7.9667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792   -6.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6125   -5.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875   -5.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -7.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -6.7542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -6.7542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5333   -5.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8750   -7.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0375   -8.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1667   -8.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5333   -4.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6167   -9.0792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417   -7.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2458   -4.2542    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -8.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2500   -7.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -7.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2375   -8.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9000   -4.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0375   -6.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9000   -5.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792   -4.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  1  1  0
  5  2  2  0
  6  4  1  0
  7  2  1  0
  8 16  1  0
  9  8  1  0
 10  6  1  0
 11  9  1  0
 12 19  1  0
 13  3  1  0
 14 10  2  0
 15 12  1  0
 16 23  1  0
 17 14  1  0
 18 11  2  0
 19 20  2  0
 20 11  1  0
 21 18  1  0
 22 24  1  0
 23  7  1  0
 24  6  2  0
 25 22  2  0
 14 25  1  0
 21 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA194868

   (2E)-N-[2-[(4-aminophenyl)disulfanyl]ethyl]-3-(3-bromophenyl)-2-hydroxyimino-propanamide

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: 440.39

Molecular Weight (Monoisotopic): 439.0024

AlogP: 3.96

#Rotatable Bonds: 8

Polar Surface Area: 87.71

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.65

CX Basic pKa: 4.07

CX LogP: 3.80

CX LogD: 3.78

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.14

Np Likeness Score: -0.10

References

1. Nicolaou KC..  (2005)  Joys of molecules. 2. Endeavors in chemical biology and medicinal chemistry.,  48  (18): [PMID:16134928] [10.1021/jm050524f]

2. Nicolaou KC..  (2005)  Joys of molecules. 2. Endeavors in chemical biology and medicinal chemistry.,  48  (18): [PMID:16134928] [10.1021/jm050524f]

Source

Source(1):

• Scientific Literature