ID: ALA2047813

Max Phase: Preclinical

Molecular Formula: C17H15N3O4S

Molecular Weight: 357.39

Molecule Type: Small molecule

Representations

Synonyms (1): 4-[(1-Naphtyl)Ureido]Phenyl Sulfamate
Synonyms from Alternative Forms(1):

Canonical SMILES:  NS(=O)(=O)Oc1ccc(NC(=O)Nc2cccc3ccccc23)cc1

Standard InChI:  InChI=1S/C17H15N3O4S/c18-25(22,23)24-14-10-8-13(9-11-14)19-17(21)20-16-7-3-5-12-4-1-2-6-15(12)16/h1-11H,(H2,18,22,23)(H2,19,20,21)

Standard InChI Key:  AIRAKQOXEIFHQE-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: 357.39

Molecular Weight (Monoisotopic): 357.0783

AlogP: 3.07

#Rotatable Bonds: 4

Polar Surface Area: 110.52

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.63

CX Basic pKa:

CX LogP: 2.75

CX LogD: 2.75

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.67

Np Likeness Score: -1.34

References

1. Winum JY, Carta F, Ward C, Mullen P, Harrison D, Langdon SP, Cecchi A, Scozzafava A, Kunkler I, Supuran CT..  (2012)  Ureido-substituted sulfamates show potent carbonic anhydrase IX inhibitory and antiproliferative activities against breast cancer cell lines.,  22  (14): [PMID:22721713] [10.1016/j.bmcl.2012.05.083]

2. Tarko L, Supuran CT..  (2013)  QSAR studies of sulfamate and sulfamide inhibitors targeting human carbonic anhydrase isozymes I, II, IX and XII.,  21  (6): [PMID:23206986] [10.1016/j.bmc.2012.11.004]

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