{(2R,3R,6S)-3-(acetyloxy)-6-[(aminosulfonyl)amino]-3,6-dihydro-2H-pyran-2-yl}methyl acetate

ID: ALA236052

Chembl Id: CHEMBL236052

Max Phase: Preclinical

Molecular Formula: C10H16N2O7S

Molecular Weight: 308.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H]1O[C@H](NS(N)(=O)=O)C=C[C@H]1OC(C)=O

Standard InChI:  InChI=1S/C10H16N2O7S/c1-6(13)17-5-9-8(18-7(2)14)3-4-10(19-9)12-20(11,15)16/h3-4,8-10,12H,5H2,1-2H3,(H2,11,15,16)/t8-,9-,10+/m1/s1

Standard InChI Key:  HHTMGBZKMBVDFX-BBBLOLIVSA-N

Alternative Forms

1. Parent:

   

   ALA236052

   ---

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: 308.31

Molecular Weight (Monoisotopic): 308.0678

AlogP: -1.44

#Rotatable Bonds: 5

Polar Surface Area: 134.02

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.23

CX Basic pKa: ┄

CX LogP: -1.51

CX LogD: -1.51

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.47

Np Likeness Score: 1.07

References

1. Colinas PA, Bravo RD, Vullo D, Scozzafava A, Supuran CT..  (2007)  Carbonic anhydrase inhibitors. Inhibition of cytosolic isoforms I and II, and extracellular isoforms IV, IX, and XII with sulfamides incorporating sugar moieties.,  17  (18): [PMID:17658252] [10.1016/j.bmcl.2007.07.023]

2. Crespo R, de Bravo MG, Colinas PA, Bravo RD..  (2010)  In vitro antitumor activity of N-glycosyl sulfonamides.,  20  (22): [PMID:20888767] [10.1016/j.bmcl.2010.09.052]

3. Winum JY, Colinas PA, Supuran CT..  (2013)  Glycosidic carbonic anhydrase IX inhibitors: a sweet approach against cancer.,  21  (6): [PMID:23199483] [10.1016/j.bmc.2012.10.043]

Source

Source(1):

• Scientific Literature