(2R,5R)-1-[4-(2-Bromo-benzyloxy)-benzenesulfonyl]-5-hydroxy-3,3-dimethyl-piperidine-2-carboxylic acid hydroxyamide

ID: ALA372261

PubChem CID: 44399731

Max Phase: Preclinical

Molecular Formula: C21H25BrN2O6S

Molecular Weight: 513.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)C[C@@H](O)CN(S(=O)(=O)c2ccc(OCc3ccccc3Br)cc2)[C@H]1C(=O)NO

Standard InChI:  InChI=1S/C21H25BrN2O6S/c1-21(2)11-15(25)12-24(19(21)20(26)23-27)31(28,29)17-9-7-16(8-10-17)30-13-14-5-3-4-6-18(14)22/h3-10,15,19,25,27H,11-13H2,1-2H3,(H,23,26)/t15-,19+/m1/s1

Standard InChI Key:  MRBPTYYVXXZQBB-BEFAXECRSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  1  0  0  0  0  0999 V2000
    3.6125   -2.3875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125   -3.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917   -3.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917   -4.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -3.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -3.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4375   -2.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7875   -2.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -4.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667    0.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -2.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -4.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667   -3.6250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7792    1.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542    1.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -1.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375    0.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6292    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7875    2.1458    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.0667   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -5.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9125   -0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -0.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -3.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -4.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542    0.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917    0.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7667   -0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4875    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
  3  5  1  6
  6  2  1  0
  7  1  1  0
  8  1  2  0
  9  1  2  0
 10 13  1  0
 11 16  1  0
 12  5  2  0
 13  6  1  0
 14  5  1  0
 15 11  1  0
 16 19  1  0
 17  7  1  0
 18  7  2  0
 19 20  1  0
 20 24  2  0
 21 15  1  0
 22  4  1  0
 23  4  1  0
 24 18  1  0
 25 17  2  0
 26 14  1  0
 13 27  1  6
 28 11  2  0
 29 15  2  0
 30 28  1  0
 31 30  2  0
 20 25  1  0
 10  4  1  0
 31 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA372261

   (2R,5R)-1-[4-(2-Bromo-benzyloxy)-benzenesulfonyl]-5-hydroxy-3,3-dimethyl-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: 513.41

Molecular Weight (Monoisotopic): 512.0617

AlogP: 2.68

#Rotatable Bonds: 6

Polar Surface Area: 116.17

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.71

CX Basic pKa: ┄

CX LogP: 2.76

CX LogD: 2.74

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.40

Np Likeness Score: -0.61

References

1. Noe MC, Natarajan V, Snow SL, Mitchell PG, Lopresti-Morrow L, Reeves LM, Yocum SA, Carty TJ, Barberia JA, Sweeney FJ, Liras JL, Vaughn M, Hardink JR, Hawkins JM, Tokar C..  (2005)  Discovery of 3,3-dimethyl-5-hydroxypipecolic hydroxamate-based inhibitors of aggrecanase and MMP-13.,  15  (11): [PMID:15911259] [10.1016/j.bmcl.2005.03.105]

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

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data