(2R,3S)4-[4-(5-fluoro-2-methylbenzyloxy)-benzenesulfonyl]-3-methyl-4-carboxylicacidmethylamidepiperazine-2-carboxylicacid hydroxyamide

ID: ALA3981624

PubChem CID: 58619818

Max Phase: Preclinical

Molecular Formula: C22H27FN4O6S

Molecular Weight: 494.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)N1CCN(S(=O)(=O)c2ccc(OCc3cc(F)ccc3C)cc2)[C@@H](C(=O)NO)[C@@H]1C

Standard InChI:  InChI=1S/C22H27FN4O6S/c1-14-4-5-17(23)12-16(14)13-33-18-6-8-19(9-7-18)34(31,32)27-11-10-26(22(29)24-3)15(2)20(27)21(28)25-30/h4-9,12,15,20,30H,10-11,13H2,1-3H3,(H,24,29)(H,25,28)/t15-,20+/m0/s1

Standard InChI Key:  AKDAOGVCHLXHKE-MGPUTAFESA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3981624

   (2S,3R)-4-[4-[(5-fluoro-2-methylphenyl)methoxy]phenyl]sulfonyl-3-N-hydroxy-1-N,2-dimethylpiperazine-1,3-dicarboxamide

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: 494.55

Molecular Weight (Monoisotopic): 494.1635

AlogP: 1.62

#Rotatable Bonds: 6

Polar Surface Area: 128.28

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.70

CX Basic pKa: ┄

CX LogP: 1.51

CX LogD: 1.49

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.41

Np Likeness Score: -1.15

References

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

Source

Source(1):

• Patent Bioactivity Data