N-[2-(3,4-dihydroxyphenyl)ethyl]-4-sulfamoylbenzamide

ID: ALA3613775

PubChem CID: 122189300

Max Phase: Preclinical

Molecular Formula: C15H16N2O5S

Molecular Weight: 336.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)c1ccc(C(=O)NCCc2ccc(O)c(O)c2)cc1

Standard InChI:  InChI=1S/C15H16N2O5S/c16-23(21,22)12-4-2-11(3-5-12)15(20)17-8-7-10-1-6-13(18)14(19)9-10/h1-6,9,18-19H,7-8H2,(H,17,20)(H2,16,21,22)

Standard InChI Key:  UMFITWUAMUVHJD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    3.6499  -12.6011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6110  -12.0005    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5716  -12.6002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031   -3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039   -3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070   -5.2502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6078   -5.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6109   -7.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6460   -5.3970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9100   -8.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9100   -9.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6110  -10.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3119   -9.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3119   -8.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6105  -13.2005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 14  1  0
 18  2  1  0
  2 21  1  0
  7 22  1  0
  6 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3613775

   ---

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: 336.37

Molecular Weight (Monoisotopic): 336.0780

AlogP: 0.72

#Rotatable Bonds: 5

Polar Surface Area: 129.72

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.20

CX Basic pKa: ┄

CX LogP: 1.06

CX LogD: 1.05

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.60

Np Likeness Score: -0.68

References

1. Buemi MR, De Luca L, Ferro S, Bruno E, Ceruso M, Supuran CT, Pospíšilová K, Brynda J, Řezáčová P, Gitto R..  (2015)  Carbonic anhydrase inhibitors: Design, synthesis and structural characterization of new heteroaryl-N-carbonylbenzenesulfonamides targeting druggable human carbonic anhydrase isoforms.,  102  [PMID:26276436] [10.1016/j.ejmech.2015.07.049]

2. Ferro S, Gitto R, Buemi MR, Karamanou S, Stevaert A, Naesens L, De Luca L..  (2018)  Identification of influenza PA-Nter endonuclease inhibitors using pharmacophore- and docking-based virtual screening.,  26  (15): [PMID:30082105] [10.1016/j.bmc.2018.07.046]

Source

Source(1):

• Scientific Literature