ID: ALA2047796

Max Phase: Preclinical

Molecular Formula: C13H13N3O4S

Molecular Weight: 307.33

Molecule Type: Small molecule

Representations

Synonyms (2): 4-(3-Phenylureido)Phenyl Sulfamate | 4-[Phenylureido]Phenyl Sulfamate
Synonyms from Alternative Forms(2):

Canonical SMILES:  NS(=O)(=O)Oc1ccc(NC(=O)Nc2ccccc2)cc1

Standard InChI:  InChI=1S/C13H13N3O4S/c14-21(18,19)20-12-8-6-11(7-9-12)16-13(17)15-10-4-2-1-3-5-10/h1-9H,(H2,14,18,19)(H2,15,16,17)

Standard InChI Key:  XBROHMNXVHEVJW-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: 307.33

Molecular Weight (Monoisotopic): 307.0627

AlogP: 1.91

#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: 10.68

CX Basic pKa:

CX LogP: 1.76

CX LogD: 1.76

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.80

Np Likeness Score: -1.15

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