(2R,5R)1-[4-(2-fluoro-5-chlorobenzyloxy)-benzenesulfonyl]-5-hydroxy-3,3-dimethylpiperidine-2-carboxylicacid hydroxyamide

ID: ALA3909799

PubChem CID: 58619815

Max Phase: Preclinical

Molecular Formula: C21H24ClFN2O6S

Molecular Weight: 486.95

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)C[C@@H](O)CN(S(=O)(=O)c2ccc(OCc3cc(Cl)ccc3F)cc2)[C@H]1C(=O)NO

Standard InChI:  InChI=1S/C21H24ClFN2O6S/c1-21(2)10-15(26)11-25(19(21)20(27)24-28)32(29,30)17-6-4-16(5-7-17)31-12-13-9-14(22)3-8-18(13)23/h3-9,15,19,26,28H,10-12H2,1-2H3,(H,24,27)/t15-,19+/m1/s1

Standard InChI Key:  XOODFFUDKRERSH-BEFAXECRSA-N

Molfile:  

     RDKit          2D

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    6.2982   -6.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5929   -6.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1731   -5.1219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5003   -6.2512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6836   -6.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7322   -7.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1100   -6.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1529   -5.5314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5615   -6.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3787   -6.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7873   -5.5314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6045   -5.5314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0131   -6.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6045   -6.9468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7873   -6.9468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3787   -4.8237    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.0131   -7.6545    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.9815   -8.3591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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  5  4  2  0
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  9 10  1  0
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  7 11  1  0
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 12 14  1  0
  8 12  1  6
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 17 18  2  0
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  5 16  1  0
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 24 25  1  0
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  7  5  1  0
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 28 31  1  0
 10 32  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3909799

   (2R,5R)-1-[4-[(5-chloro-2-fluorophenyl)methoxy]phenyl]sulfonyl-N,5-dihydroxy-3,3-dimethylpiperidine-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: 486.95

Molecular Weight (Monoisotopic): 486.1028

AlogP: 2.71

#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: 8.71

CX Basic pKa: ┄

CX LogP: 2.74

CX LogD: 2.72

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.43

Np Likeness Score: -0.99

References

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

Source

Source(1):

• Patent Bioactivity Data