(2R,3R)1-[4-(2-fluoro-4-chlorobenzyloxy)-benzenesulfonyl]-3-hydroxy-3-methyl-piperidine-2-carboxylicacid hydroxyamide

ID: ALA3979213

PubChem CID: 134151538

Max Phase: Preclinical

Molecular Formula: C21H25ClN2O6S

Molecular Weight: 468.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(Cl)ccc1COc1ccc(S(=O)(=O)N2CCC[C@@](C)(O)[C@@H]2C(=O)NO)cc1

Standard InChI:  InChI=1S/C21H25ClN2O6S/c1-14-12-16(22)5-4-15(14)13-30-17-6-8-18(9-7-17)31(28,29)24-11-3-10-21(2,26)19(24)20(25)23-27/h4-9,12,19,26-27H,3,10-11,13H2,1-2H3,(H,23,25)/t19-,21+/m0/s1

Standard InChI Key:  YZTJOVZZAVKUOK-PZJWPPBQSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    7.0411   -5.1136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7509   -5.5222    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7498   -4.7032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3682   -6.2430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5515   -6.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1675   -6.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6001   -7.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4168   -7.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8009   -6.9362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1189   -5.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5029   -4.8564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3022   -5.6058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8695   -4.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5238   -6.4889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5693   -5.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9779   -4.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.2037   -5.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7951   -6.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9779   -6.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0209   -5.5232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4295   -6.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2466   -6.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6552   -5.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4724   -5.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8810   -6.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4724   -6.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6552   -6.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6982   -6.2309    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.2466   -4.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
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  8  9  1  0
  4  9  1  0
 10 11  2  0
 12 13  1  0
 10 12  1  0
  5 10  1  6
  6 14  1  0
  6 15  1  1
 16 17  1  0
 17 18  2  0
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 19 20  2  0
 20 21  1  0
 16 21  2  0
  2 16  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 24 29  2  0
 22 23  1  0
 27 30  1  0
 25 31  1  0
 19 22  1  0
  4  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3979213

   ---

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: 468.96

Molecular Weight (Monoisotopic): 468.1122

AlogP: 2.64

#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: 2.65

CX LogD: 2.62

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.44

Np Likeness Score: -0.91

References

1.  (2001)  Selective inhibitors of aggrecanase in osteoarthritis treatment, 

Source

Source(1):

• Patent Bioactivity Data