ID: ALA2047839

Max Phase: Preclinical

Molecular Formula: C14H12N4O4S

Molecular Weight: 332.34

Molecule Type: Small molecule

Representations

Synonyms (1): 4-[(2-Cyanophenyl)Ureido]Phenyl Sulfamate
Synonyms from Alternative Forms(1):

Canonical SMILES:  N#Cc1ccccc1NC(=O)Nc1ccc(OS(N)(=O)=O)cc1

Standard InChI:  InChI=1S/C14H12N4O4S/c15-9-10-3-1-2-4-13(10)18-14(19)17-11-5-7-12(8-6-11)22-23(16,20)21/h1-8H,(H2,16,20,21)(H2,17,18,19)

Standard InChI Key:  HDMSKTALDJMCHU-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: 332.34

Molecular Weight (Monoisotopic): 332.0579

AlogP: 1.78

#Rotatable Bonds: 4

Polar Surface Area: 134.31

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.45

CX Basic pKa:

CX LogP: 1.62

CX LogD: 1.62

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.78

Np Likeness Score: -1.81

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