4-[phenethylureido]phenyl sulfamate

ID: ALA2047807

Chembl Id: CHEMBL2047807

PubChem CID: 60155121

Max Phase: Preclinical

Molecular Formula: C15H17N3O4S

Molecular Weight: 335.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 4-(3'-Phenethylureido)Phenyl Sulfamate | 4-(3-Phenethylureido)Phenyl Sulfamate | 4-[Phenethylureido]Phenyl Sulfamate | CHEMBL2047807|4-[Phenethylureido]Phenyl Sulfamate|BDBM50387127|4-(3-Phenethylureido)Phenyl Sulfamate|4-(3'-Phenethylureido)Phenyl Sulfamate

Canonical SMILES:  NS(=O)(=O)Oc1ccc(NC(=O)NCCc2ccccc2)cc1

Standard InChI:  InChI=1S/C15H17N3O4S/c16-23(20,21)22-14-8-6-13(7-9-14)18-15(19)17-11-10-12-4-2-1-3-5-12/h1-9H,10-11H2,(H2,16,20,21)(H2,17,18,19)

Standard InChI Key:  BGURBSUNICIDAK-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2047807

   4-[Phenethylureido]Phenyl Sulfamate

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

Calculated Properties

Molecular Weight: 335.39

Molecular Weight (Monoisotopic): 335.0940

AlogP: 1.63

#Rotatable Bonds: 6

Polar Surface Area: 110.52

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.75

CX Basic pKa: ┄

CX LogP: 1.76

CX LogD: 1.76

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.74

Np Likeness Score: -1.30

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. Gieling RG, Babur M, Mamnani L, Burrows N, Telfer BA, Carta F, Winum JY, Scozzafava A, Supuran CT, Williams KJ..  (2012)  Antimetastatic effect of sulfamate carbonic anhydrase IX inhibitors in breast carcinoma xenografts.,  55  (11): [PMID:22621623] [10.1021/jm300529u]

3. 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]

4. 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