(S)-1-(2-(Benzo[d][1,3]dioxol-5-yl)ethylsulfonyl)-N-hydroxypyrrolidine-2-carboxamide

ID: ALA2385489

PubChem CID: 73354941

Max Phase: Preclinical

Molecular Formula: C14H18N2O6S

Molecular Weight: 342.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NO)[C@@H]1CCCN1S(=O)(=O)CCc1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C14H18N2O6S/c17-14(15-18)11-2-1-6-16(11)23(19,20)7-5-10-3-4-12-13(8-10)22-9-21-12/h3-4,8,11,18H,1-2,5-7,9H2,(H,15,17)/t11-/m0/s1

Standard InChI Key:  XYXRFODFDUOQKS-NSHDSACASA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    3.0057  -14.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6641  -14.7731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3426  -14.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1071  -13.5143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2798  -13.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136  -14.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160  -13.9400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0227  -15.3140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8239  -14.1762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6393  -15.6006    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3658  -15.9933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0699  -15.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7963  -15.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8155  -15.6019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2293  -16.3172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8178  -16.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2219  -15.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4958  -15.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2478  -16.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5476  -17.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7421  -17.9676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5627  -18.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8752  -17.2684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  1  6  1  6
  6  7  1  0
  6  8  2  0
  7  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 10 14  2  0
 15 10  2  0
 13 16  2  0
 16 20  1  0
 19 17  1  0
 17 18  2  0
 18 13  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2385489

   (2S)-1-[2-(1,3-benzodioxol-5-yl)ethylsulfonyl]-N-hydroxypyrrolidine-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: 342.37

Molecular Weight (Monoisotopic): 342.0886

AlogP: 0.26

#Rotatable Bonds: 5

Polar Surface Area: 105.17

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.71

CX Basic pKa: ┄

CX LogP: -0.01

CX LogD: -0.03

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.59

Np Likeness Score: -0.94

References

1. Mori M, Massaro A, Calderone V, Fragai M, Luchinat C, Mordini A..  (2013)  Discovery of a New Class of Potent MMP Inhibitors by Structure-Based Optimization of the Arylsulfonamide Scaffold.,  4  (6): [PMID:24900710] [10.1021/ml300446a]

Source

Source(1):

• Scientific Literature