Sulfamic acid 8-sulfamoyloxy-octyl ester

ID: ALA182455

Chembl Id: CHEMBL182455

PubChem CID: 20043772

Max Phase: Preclinical

Molecular Formula: C8H20N2O6S2

Molecular Weight: 304.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Octane-1,8-Diyl Disulfamate | Octane-1,8-Diyl Disulfamate|CHEMBL182455|3ibl|bis-sulfamate, 3|1,8-Octanediol disulfamate|SCHEMBL10352171|BDBM33281|IPTXSYCLIWBHBX-UHFFFAOYSA-N|1,8-bis-O-sulfamyl-1,8-octanediol|Q27464035|O59

Canonical SMILES:  NS(=O)(=O)OCCCCCCCCOS(N)(=O)=O

Standard InChI:  InChI=1S/C8H20N2O6S2/c9-17(11,12)15-7-5-3-1-2-4-6-8-16-18(10,13)14/h1-8H2,(H2,9,11,12)(H2,10,13,14)

Standard InChI Key:  IPTXSYCLIWBHBX-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA182455

   Octane-1,8-Diyl Disulfamate

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: 304.39

Molecular Weight (Monoisotopic): 304.0763

AlogP: -0.23

#Rotatable Bonds: 11

Polar Surface Area: 138.78

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.36

CX Basic pKa: ┄

CX LogP: 0.11

CX LogD: 0.11

Aromatic Rings: ┄

Heavy Atoms: 18

QED Weighted: 0.51

Np Likeness Score: -0.06

References

1. Winum JY, Pastorekova S, Jakubickova L, Montero JL, Scozzafava A, Pastorek J, Vullo D, Innocenti A, Supuran CT..  (2005)  Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with bis-sulfamates.,  15  (3): [PMID:15664816] [10.1016/j.bmcl.2004.11.058]

2. Vitale RM, Alterio V, Innocenti A, Winum JY, Monti SM, De Simone G, Supuran CT..  (2009)  Carbonic anhydrase inhibitors. Comparison of aliphatic sulfamate/bis-sulfamate adducts with isozymes II and IX as a platform for designing tight-binding, more isoform-selective inhibitors.,  52  (19): [PMID:19731956] [10.1021/jm900641r]

3. Joseph P, Ouahrani-Bettache S, Montero JL, Nishimori I, Minakuchi T, Vullo D, Scozzafava A, Winum JY, Köhler S, Supuran CT..  (2011)  A new β-carbonic anhydrase from Brucella suis, its cloning, characterization, and inhibition with sulfonamides and sulfamates, leading to impaired pathogen growth.,  19  (3): [PMID:21251841] [10.1016/j.bmc.2010.12.048]

Source

Source(1):

• Scientific Literature