(R)-4-Dimethylsulfamoyl-1-[4-(4-fluoro-phenyl)-3,6-dihydro-2H-pyridine-1-sulfonyl]-piperazine-2-carboxylic acid hydroxyamide

ID: ALA339766

PubChem CID: 18727211

Max Phase: Preclinical

Molecular Formula: C18H26FN5O6S2

Molecular Weight: 491.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)S(=O)(=O)N1CCN(S(=O)(=O)N2CC=C(c3ccc(F)cc3)CC2)[C@@H](C(=O)NO)C1

Standard InChI:  InChI=1S/C18H26FN5O6S2/c1-21(2)31(27,28)23-11-12-24(17(13-23)18(25)20-26)32(29,30)22-9-7-15(8-10-22)14-3-5-16(19)6-4-14/h3-7,17,26H,8-13H2,1-2H3,(H,20,25)/t17-/m1/s1

Standard InChI Key:  HNYFEXVRCNMJLW-QGZVFWFLSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  1  0  0  0  0  0999 V2000
    5.4917    1.3833    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5250    0.5458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -1.9417    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8250    0.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5875   -1.1042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292    1.4083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917    0.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2542    0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2792   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9792    1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417   -2.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292    2.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4625    2.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542    1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -1.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4500   -1.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7125    2.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667    0.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667    1.3208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5917    0.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917    0.0583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1917    2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2417    0.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4542    1.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0625    0.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0167    2.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2917    1.5833    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625    0.4500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9417   -3.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3750   -3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  5  1  0
  4  2  1  0
  5 10  1  0
  4  6  1  0
  7  1  1  0
  4  8  1  6
  9  2  1  0
 10  9  1  0
 11 22  1  0
 12  3  1  0
 13 18  1  0
 14  1  2  0
 15  1  2  0
 16  3  2  0
 17  3  2  0
 18  7  1  0
 19 11  1  0
 20  7  1  0
 21  8  2  0
 22 20  1  0
 23  8  1  0
 24 19  2  0
 25 19  1  0
 26 27  1  0
 27 25  2  0
 28 24  1  0
 29 26  1  0
 30 23  1  0
 31 12  1  0
 32 12  1  0
 13 11  2  0
  5  6  1  0
 28 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA339766

   (2R)-4-(dimethylsulfamoyl)-1-[[4-(4-fluorophenyl)-3,6-dihydro-2H-pyridin-1-yl]sulfonyl]-N-hydroxypiperazine-2-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: 491.57

Molecular Weight (Monoisotopic): 491.1309

AlogP: -0.54

#Rotatable Bonds: 6

Polar Surface Area: 130.57

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.70

CX Basic pKa: 0.13

CX LogP: -1.35

CX LogD: -1.37

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.41

Np Likeness Score: -1.26

References

1. Chen JJ, Dewdney N, Lin X, Martin RL, Walker KA, Huang J, Chu F, Eugui E, Mirkovich A, Kim Y, Sarma K, Arzeno H, Van Wart HE..  (2003)  Design and synthesis of orally active inhibitors of TNF synthesis as anti-rheumatoid arthritis drugs.,  13  (22): [PMID:14592482] [10.1016/j.bmcl.2003.08.076]

Source

Source(1):

• Scientific Literature