i(2R,3R)-1-[4-(2-Chloro-benzyloxy)-benzenesulfonyl]-3-hydroxy-3-methyl-piperidine-2-carboxylic acid hydroxyamide

ID: ALA183474

PubChem CID: 44394916

Max Phase: Preclinical

Molecular Formula: C20H23ClN2O6S

Molecular Weight: 454.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]1(O)CCCN(S(=O)(=O)c2ccc(OCc3ccccc3Cl)cc2)[C@H]1C(=O)NO

Standard InChI:  InChI=1S/C20H23ClN2O6S/c1-20(25)11-4-12-23(18(20)19(24)22-26)30(27,28)16-9-7-15(8-10-16)29-13-14-5-2-3-6-17(14)21/h2-3,5-10,18,25-26H,4,11-13H2,1H3,(H,22,24)/t18-,20+/m0/s1

Standard InChI Key:  NIBQFPHLKYOWJP-AZUAARDMSA-N

Molfile:  

     RDKit          2D

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   -0.1208   -0.1875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208    0.6375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5917    1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3042    0.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1250   -1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5917    1.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -0.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9458   -0.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2750   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7125   -0.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167    1.0500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -3.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8458   -1.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792   -1.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1500   -3.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5875    2.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -4.7167    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8583   -2.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5750   -2.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292    0.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208    2.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333    1.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3875    2.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7000   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7000   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  3  4  1  6
  5  1  1  0
  6  3  1  0
  7  1  2  0
  8  1  2  0
  9 13  1  0
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 18 22  1  0
  6 19  1  1
 20 12  1  0
 21 15  1  0
 22 16  2  0
 23 11  1  0
 24 25  1  0
 25 14  1  0
  6 26  1  6
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 29 27  2  0
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 18 21  2  0
 24  6  1  0
 30 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA183474

   i(2R,3R)-1-[4-(2-Chloro-benzyloxy)-benzenesulfonyl]-3-hydroxy-3-methyl-piperidine-2-carboxylic acid hydroxyamide

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: 454.93

Molecular Weight (Monoisotopic): 454.0965

AlogP: 2.33

#Rotatable Bonds: 6

Polar Surface Area: 116.17

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.68

CX Basic pKa: ┄

CX LogP: 2.13

CX LogD: 2.11

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.46

Np Likeness Score: -0.95

References

1. Noe MC, Natarajan V, Snow SL, Wolf-Gouveia LA, Mitchell PG, Lopresti-Morrow L, Reeves LM, Yocum SA, Otterness I, Bliven MA, Carty TJ, Barberia JT, Sweeney FJ, Liras JL, Vaughn M..  (2005)  Discovery of 3-OH-3-methylpipecolic hydroxamates: potent orally active inhibitors of aggrecanase and MMP-13.,  15  (14): [PMID:15953722] [10.1016/j.bmcl.2005.05.037]

2.  (2001)  Selective inhibitors of aggrecanase in osteoarthritis treatment, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data