ID: ALA1643291

Max Phase: Preclinical

Molecular Formula: C13H12BrN3O3S

Molecular Weight: 370.23

Molecule Type: Small molecule

Representations

Synonyms (1): 4-({[(4'-Bromophenyl)Amino]Carbonyl}Amino)Benzenesulfonamide
Synonyms from Alternative Forms(1):

Canonical SMILES:  NS(=O)(=O)c1ccc(NC(=O)Nc2ccc(Br)cc2)cc1

Standard InChI:  InChI=1S/C13H12BrN3O3S/c14-9-1-3-10(4-2-9)16-13(18)17-11-5-7-12(8-6-11)21(15,19)20/h1-8H,(H2,15,19,20)(H2,16,17,18)

Standard InChI Key:  DXQKMYKLTXOZRT-UHFFFAOYSA-N

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

Properties

Molecular Weight: 370.23

Molecular Weight (Monoisotopic): 368.9783

AlogP: 2.74

#Rotatable Bonds: 3

Polar Surface Area: 101.29

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.19

CX Basic pKa:

CX LogP: 2.49

CX LogD: 2.49

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.77

Np Likeness Score: -1.58

References

1. Pacchiano F, Carta F, Vullo D, Scozzafava A, Supuran CT..  (2011)  Inhibition of β-carbonic anhydrases with ureido-substituted benzenesulfonamides.,  21  (1): [PMID:21145236] [10.1016/j.bmcl.2010.11.064]

2. Pacchiano F, Carta F, McDonald PC, Lou Y, Vullo D, Scozzafava A, Dedhar S, Supuran CT..  (2011)  Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis.,  54  (6): [PMID:21361354] [10.1021/jm101541x]

3. Vullo D, Leewattanapasuk W, Mühlschlegel FA, Mastrolorenzo A, Capasso C, Supuran CT..  (2013)  Carbonic anhydrase inhibitors: inhibition of the β-class enzyme from the pathogenic yeast Candida glabrata with sulfonamides, sulfamates and sulfamides.,  23  (9): [PMID:23511020] [10.1016/j.bmcl.2013.02.092]

Source

Source(1):

• Scientific Literature