1-Benzyl-4-[4-(4-chloro-phenoxy)-benzenesulfonyl]-piperidine-4-carboxylic acid hydroxyamide

ID: ALA79433

PubChem CID: 9957653

Max Phase: Preclinical

Molecular Formula: C25H25ClN2O5S

Molecular Weight: 501.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NO)C1(S(=O)(=O)c2ccc(Oc3ccc(Cl)cc3)cc2)CCN(Cc2ccccc2)CC1

Standard InChI:  InChI=1S/C25H25ClN2O5S/c26-20-6-8-21(9-7-20)33-22-10-12-23(13-11-22)34(31,32)25(24(29)27-30)14-16-28(17-15-25)18-19-4-2-1-3-5-19/h1-13,30H,14-18H2,(H,27,29)

Standard InChI Key:  IMKDKHQDFFLOKK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
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    0.4421  -11.3011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4374  -12.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1483  -12.5405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8719  -11.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444  -10.4824    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746  -10.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9837  -10.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2634  -11.7175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0250   -9.7623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1236  -10.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8396  -10.4964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5539  -10.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5477  -11.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8311  -12.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2712  -10.5035    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5901  -10.8903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8736   -9.6526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3047  -10.4766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1405  -13.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8518  -13.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8411  -14.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5515  -15.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2714  -14.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2764  -13.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653  -13.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0
 12 17  1  0
  2  3  1  0
 17 18  1  0
  6  9  1  0
 18 19  2  0
  3  4  1  0
 19 20  1  0
  9 10  2  0
 20 21  2  0
  4  8  1  0
 21 22  1  0
 10 11  1  0
 22 23  2  0
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  8  5  1  0
 21 24  1  0
 11 12  2  0
  7 25  1  0
  1  2  1  0
  7 26  2  0
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 25 27  1  0
  6  1  1  0
  4 28  1  0
 13 14  2  0
 28 29  1  0
 14  9  1  0
 29 30  2  0
 30 31  1  0
  6 15  2  0
 31 32  2  0
  1  7  1  0
 32 33  1  0
  6 16  2  0
 33 34  2  0
 34 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA79433

   1-benzyl-4-(4-(4-chlorophenoxy)phenylsulfonyl)-N-hydroxypiperidine-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: 501.00

Molecular Weight (Monoisotopic): 500.1173

AlogP: 4.45

#Rotatable Bonds: 7

Polar Surface Area: 95.94

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.66

CX Basic pKa: 6.38

CX LogP: 4.02

CX LogD: 3.96

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.37

Np Likeness Score: -0.96

References

1. Aranapakam V, Davis JM, Grosu GT, Baker J, Ellingboe J, Zask A, Levin JI, Sandanayaka VP, Du M, Skotnicki JS, DiJoseph JF, Sung A, Sharr MA, Killar LM, Walter T, Jin G, Cowling R, Tillett J, Zhao W, McDevitt J, Xu ZB..  (2003)  Synthesis and structure-activity relationship of N-substituted 4-arylsulfonylpiperidine-4-hydroxamic acids as novel, orally active matrix metalloproteinase inhibitors for the treatment of osteoarthritis.,  46  (12): [PMID:12773042] [10.1021/jm0205550]

2. Fernández M, Caballero J..  (2007)  QSAR modeling of matrix metalloproteinase inhibition by N-hydroxy-alpha-phenylsulfonylacetamide derivatives.,  15  (18): [PMID:17590339] [10.1016/j.bmc.2007.06.014]

3. Flipo M, Charton J, Hocine A, Dassonneville S, Deprez B, Deprez-Poulain R..  (2009)  Hydroxamates: relationships between structure and plasma stability.,  52  (21): [PMID:19821586] [10.1021/jm900648x]

4. Atobe M, Maekawara N, Ishiguro N, Sogame S, Suenaga Y, Kawanishi M, Suzuki H, Jinno N, Tanaka E, Miyoshi S..  (2013)  A series of thiazole derivatives bearing thiazolidin-4-one as non-competitive ADAMTS-5 (aggrecanase-2) inhibitors.,  23  (7): [PMID:23453070] [10.1016/j.bmcl.2013.01.121]

Source

Source(1):

• Scientific Literature