(S)-3-((4-(4-Cyano-2-methylphenyl)piperazin-1-yl)sulfonyl)-N-hydroxythiazolidine-4-carboxamide

ID: ALA3770935

PubChem CID: 117094707

Max Phase: Preclinical

Molecular Formula: C16H21N5O4S2

Molecular Weight: 411.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C#N)ccc1N1CCN(S(=O)(=O)N2CSC[C@@H]2C(=O)NO)CC1

Standard InChI:  InChI=1S/C16H21N5O4S2/c1-12-8-13(9-17)2-3-14(12)19-4-6-20(7-5-19)27(24,25)21-11-26-10-15(21)16(22)18-23/h2-3,8,15,23H,4-7,10-11H2,1H3,(H,18,22)/t15-/m1/s1

Standard InChI Key:  UGVOWFLXYXPRQV-OAHLLOKOSA-N

Molfile:  

     RDKit          2D

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    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 N   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 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.0008    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2993   -3.7521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0394   -3.6005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0391   -2.4007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3002    3.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3026    5.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0048    6.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2954    5.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2978    3.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0072    7.5017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0091    8.7017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3380    3.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4361   -5.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9031   -5.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6540   -4.2472    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6510   -3.1318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3124   -6.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5499   -7.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1104   -5.7460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0105   -6.5396    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
  5  6  1  0
  6  1  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  7 10  2  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
  3 11  1  0
 17 18  3  0
 14 17  1  0
 16 19  1  0
  8 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23  8  1  0
 20 24  1  1
 24 25  2  0
 24 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3770935

   (4s)-3-{[4-(4-Cyano-2-Methylphenyl)piperazin-1-Yl]sulfonyl}-N-Hydroxy-1,3-Thiazolidine-4-Carboxamide

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: 411.51

Molecular Weight (Monoisotopic): 411.1035

AlogP: 0.11

#Rotatable Bonds: 4

Polar Surface Area: 116.98

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.70

CX Basic pKa: 0.00

CX LogP: 0.16

CX LogD: 0.14

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.53

Np Likeness Score: -1.79

References

1. Camodeca C, Nuti E, Tepshi L, Boero S, Tuccinardi T, Stura EA, Poggi A, Zocchi MR, Rossello A..  (2016)  Discovery of a new selective inhibitor of A Disintegrin And Metalloprotease 10 (ADAM-10) able to reduce the shedding of NKG2D ligands in Hodgkin's lymphoma cell models.,  111  [PMID:26871660] [10.1016/j.ejmech.2016.01.053]

Source

Source(1):

• Scientific Literature