ID: ALA687

Max Phase: Preclinical

Molecular Formula: C8H10N2O3S

Molecular Weight: 214.25

Molecule Type: Small molecule

Representations

Synonyms (1): N4-Acetyl Metabolite
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(=O)Nc1ccc(S(N)(=O)=O)cc1

Standard InChI:  InChI=1S/C8H10N2O3S/c1-6(11)10-7-2-4-8(5-3-7)14(9,12)13/h2-5H,1H3,(H,10,11)(H2,9,12,13)

Standard InChI Key:  PKOFBDHYTMYVGJ-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

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: 214.25

Molecular Weight (Monoisotopic): 214.0412

AlogP: 0.29

#Rotatable Bonds: 2

Polar Surface Area: 89.26

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.28

CX Basic pKa:

CX LogP: -0.18

CX LogD: -0.18

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.74

Np Likeness Score: -1.82

References

1. Vullo D, Franchi M, Gallori E, Antel J, Scozzafava A, Supuran CT..  (2004)  Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides.,  47  (5): [PMID:14971907] [10.1021/jm031057+]

2. Chand P, Babu YS, Bantia S, Chu N, Cole LB, Kotian PL, Laver WG, Montgomery JA, Pathak VP, Petty SL, Shrout DP, Walsh DA, Walsh GM..  (1997)  Design and synthesis of benzoic acid derivatives as influenza neuraminidase inhibitors using structure-based drug design.,  40  (25): [PMID:9406595] [10.1021/jm970479e]

3. Menziani MC, De Benedetti PG, Gago F, Richards WG..  (1989)  The binding of benzenesulfonamides to carbonic anhydrase enzyme. A molecular mechanics study and quantitative structure-activity relationships.,  32  (5): [PMID:2709382] [10.1021/jm00125a005]

4. Ozensoy O, Puccetti L, Fasolis G, Arslan O, Scozzafava A, Supuran CT..  (2005)  Carbonic anhydrase inhibitors: inhibition of the tumor-associated isozymes IX and XII with a library of aromatic and heteroaromatic sulfonamides.,  15  (21): [PMID:16168653] [10.1016/j.bmcl.2005.08.048]

5. Huber VJ, Tsujita M, Yamazaki M, Sakimura K, Nakada T..  (2007)  Identification of arylsulfonamides as Aquaporin 4 inhibitors.,  17  (5): [PMID:17178220] [10.1016/j.bmcl.2006.12.010]

6. Yang B, Zhang H, Verkman AS..  (2008)  Lack of aquaporin-4 water transport inhibition by antiepileptics and arylsulfonamides.,  16  (15): [PMID:18572411] [10.1016/j.bmc.2008.06.005]

7. PubChem BioAssay data set, 

8. Kaur J,Cao X,Abutaleb NS,Elkashif A,Graboski AL,Krabill AD,AbdelKhalek AH,An W,Bhardwaj A,Seleem MN,Flaherty DP.  (2020)  Optimization of Acetazolamide-Based Scaffold as Potent Inhibitors of Vancomycin-Resistant Enterococcus.,  63  (17): [PMID:32787141] [10.1021/acs.jmedchem.0c00734]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays