ID: ALA1643289

Max Phase: Preclinical

Molecular Formula: C14H15N3O3S

Molecular Weight: 305.36

Molecule Type: Small molecule

Representations

Synonyms (2): 4-(3-Benzylureido)Benzenesulfonamide | 4-{[(Benzylamino)Carbonyl]Amino}Benzenesulfonamide
Synonyms from Alternative Forms(2):

Canonical SMILES:  NS(=O)(=O)c1ccc(NC(=O)NCc2ccccc2)cc1

Standard InChI:  InChI=1S/C14H15N3O3S/c15-21(19,20)13-8-6-12(7-9-13)17-14(18)16-10-11-4-2-1-3-5-11/h1-9H,10H2,(H2,15,19,20)(H2,16,17,18)

Standard InChI Key:  ISUQWNITGXDZNG-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: 305.36

Molecular Weight (Monoisotopic): 305.0834

AlogP: 1.66

#Rotatable Bonds: 4

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: 10.25

CX Basic pKa:

CX LogP: 1.43

CX LogD: 1.43

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.80

Np Likeness Score: -1.92

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