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

ID: ALA3910163

PubChem CID: 58619808

Max Phase: Preclinical

Molecular Formula: C20H22F2N2O6S

Molecular Weight: 456.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]1(O)CCCN(S(=O)(=O)c2ccc(OCc3ccc(F)cc3F)cc2)[C@H]1C(=O)NO

Standard InChI:  InChI=1S/C20H22F2N2O6S/c1-20(26)9-2-10-24(18(20)19(25)23-27)31(28,29)16-7-5-15(6-8-16)30-12-13-3-4-14(21)11-17(13)22/h3-8,11,18,26-27H,2,9-10,12H2,1H3,(H,23,25)/t18-,20+/m0/s1

Standard InChI Key:  QHWBKCVJTHLALQ-AZUAARDMSA-N

Molfile:  

     RDKit          2D

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   12.2838   -6.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6924   -5.7790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5096   -5.7790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9182   -6.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5096   -7.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6924   -7.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2838   -5.0713    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.7354   -6.4868    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA3910163

   (2R,3R)-1-[4-[(2,4-difluorophenyl)methoxy]phenyl]sulfonyl-N,3-dihydroxy-3-methylpiperidine-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: 456.47

Molecular Weight (Monoisotopic): 456.1167

AlogP: 1.95

#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: 1.81

CX LogD: 1.79

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.45

Np Likeness Score: -1.07

References

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

Source

Source(1):

• Patent Bioactivity Data