2-(phenylsulfonamido)-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid

ID: ALA380394

PubChem CID: 6102685

Max Phase: Preclinical

Molecular Formula: C17H17NO4S

Molecular Weight: 331.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1c(NS(=O)(=O)c2ccccc2)ccc2c1CCCC2

Standard InChI:  InChI=1S/C17H17NO4S/c19-17(20)16-14-9-5-4-6-12(14)10-11-15(16)18-23(21,22)13-7-2-1-3-8-13/h1-3,7-8,10-11,18H,4-6,9H2,(H,19,20)

Standard InChI Key:  RRXVUYHFDBLTEL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -3.0306   -0.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3161   -1.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6016   -0.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6016    0.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3161    0.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0306    0.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8871   -1.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1727   -0.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1727    0.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8871    0.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8871    1.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1727    1.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6016    1.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5418    0.5325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2563    0.1200    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9707   -0.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8438   -0.5944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6688    0.8345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6852    0.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3997   -0.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3997   -1.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6852   -1.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9707   -1.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  3  7  2  0
  4  5  1  0
 10  4  2  0
  5  6  1  0
  7  8  1  0
  8  9  2  0
 10  9  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 14 15  1  0
 16 15  1  0
 17 15  2  0
 18 15  2  0
 16 19  1  0
 16 23  2  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA380394

   2-[(Phenylsulfonyl)amino]-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid

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: 331.39

Molecular Weight (Monoisotopic): 331.0878

AlogP: 3.06

#Rotatable Bonds: 4

Polar Surface Area: 83.47

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.07

CX Basic pKa: ┄

CX LogP: 3.57

CX LogD: 0.39

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.90

Np Likeness Score: -0.89

References

1. Sheppard GS, Wang J, Kawai M, Fidanze SD, BaMaung NY, Erickson SA, Barnes DM, Tedrow JS, Kolaczkowski L, Vasudevan A, Park DC, Wang GT, Sanders WJ, Mantei RA, Palazzo F, Tucker-Garcia L, Lou P, Zhang Q, Park CH, Kim KH, Petros A, Olejniczak E, Nettesheim D, Hajduk P, Henkin J, Lesniewski R, Davidsen SK, Bell RL..  (2006)  Discovery and optimization of anthranilic acid sulfonamides as inhibitors of methionine aminopeptidase-2: a structural basis for the reduction of albumin binding.,  49  (13): [PMID:16789740] [10.1021/jm0601001]

2. Kawai M, BaMaung NY, Fidanze SD, Erickson SA, Tedrow JS, Sanders WJ, Vasudevan A, Park C, Hutchins C, Comess KM, Kalvin D, Wang J, Zhang Q, Lou P, Tucker-Garcia L, Bouska J, Bell RL, Lesniewski R, Henkin J, Sheppard GS..  (2006)  Development of sulfonamide compounds as potent methionine aminopeptidase type II inhibitors with antiproliferative properties.,  16  (13): [PMID:16632353] [10.1016/j.bmcl.2006.03.085]

3. Shahlaei M, Sabet R, Ziari MB, Moeinifard B, Fassihi A, Karbakhsh R..  (2010)  QSAR study of anthranilic acid sulfonamides as inhibitors of methionine aminopeptidase-2 using LS-SVM and GRNN based on principal components.,  45  (10): [PMID:20691509] [10.1016/j.ejmech.2010.07.010]

Source

Source(1):

• Scientific Literature