ID: ALA11185

Max Phase: Preclinical

Molecular Formula: C10H9NO5S

Molecular Weight: 255.25

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1cc(=O)oc2cc(OS(N)(=O)=O)ccc12

Standard InChI:  InChI=1S/C10H9NO5S/c1-6-4-10(12)15-9-5-7(2-3-8(6)9)16-17(11,13)14/h2-5H,1H3,(H2,11,13,14)

Standard InChI Key:  UFGBGFMPBMEVMI-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: 255.25

Molecular Weight (Monoisotopic): 255.0201

AlogP: 0.68

#Rotatable Bonds: 2

Polar Surface Area: 99.60

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.65

CX Basic pKa:

CX LogP: 0.73

CX LogD: 0.73

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.80

Np Likeness Score: -0.39

References

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2. Ahmed S, James K, Owen CP, Patel CK, Sampson L..  (2002)  The mechanism of the irreversible inhibition of estrone sulfatase (ES) through the consideration of a range of methane- and amino-sulfonate-based compounds.,  12  (9): [PMID:11965370] [10.1016/s0960-894x(02)00137-3]

3. Jütten P, Schumann W, Härtl A, Heinisch L, Gräfe U, Werner W, Ulbricht H..  (2002)  A novel type of nonsteroidal estrone sulfatase inhibitors.,  12  (10): [PMID:11992772] [10.1016/s0960-894x(02)00171-3]

4. Ahmed S, James K, Owen CP, Patel CK..  (2002)  Design, synthesis and biochemical evaluation of AC ring mimics as novel inhibitors of the enzyme estrone sulfatase (ES).,  12  (10): [PMID:11992773] [10.1016/s0960-894x(02)00170-1]

5. Woo LW, Purohit A, Reed MJ, Potter BV..  (1996)  Active site directed inhibition of estrone sulfatase by nonsteroidal coumarin sulfamates.,  39  (7): [PMID:8691463] [10.1021/jm950931z]

6. Ahmed S, James K..  (1999)  Derivation of a possible transition-state for the reaction catalysed by the enzyme estrone Sulfatase (ES).,  9  (12): [PMID:10397493] [10.1016/s0960-894x(99)00245-0]

7. Ahmed S, James K, Owen CP..  (2002)  Inhibition of estrone sulfatase (ES) by derivatives of 4-[(aminosulfonyl)oxy] benzoic acid.,  12  (17): [PMID:12161140] [10.1016/s0960-894x(02)00383-9]

8. Ahmed S, James K, Owen CP, Patel CK, Patel M..  (2001)  Hydrophobicity, a physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES).,  11  (18): [PMID:11549461] [10.1016/s0960-894x(01)00482-6]

9. Ahmed S, James K, Owen CP, Patel CK, Patel MB..  (2001)  Determination and use of a transition state for the enzyme estrone sulfatase (ES) from a proposed reaction mechanism.,  11  (23): [PMID:11714597] [10.1016/s0960-894x(01)00607-2]

10. Patel CK, Owen CP, Ahmed S..  (2004)  Inhibition of estrone sulfatase (ES) by alkyl and cycloalkyl ester derivatives of 4-[(aminosulfonyl)oxy] benzoic acid.,  14  (3): [PMID:14741252] [10.1016/j.bmcl.2003.11.067]

11. Ahmed S, James K, Owen CP, Patel CK, Patel M..  (2001)  Novel inhibitors of the enzyme estrone sulfatase (ES).,  11  (6): [PMID:11277533] [10.1016/s0960-894x(01)00086-5]

12. Bilban M, Billich A, Auer M, Nussbaumer P..  (2000)  New fluorogenic substrate for the first continuous steroid sulfatase assay.,  10  (9): [PMID:10853670] [10.1016/s0960-894x(00)00144-x]

13. Cecchi A, Taylor SD, Liu Y, Hill B, Vullo D, Scozzafava A, Supuran CT..  (2005)  Carbonic anhydrase inhibitors: inhibition of the human isozymes I, II, VA, and IX with a library of substituted difluoromethanesulfonamides.,  15  (23): [PMID:16203142] [10.1016/j.bmcl.2005.08.102]

14. Thomas MP, Potter BV..  (2015)  Discovery and Development of the Aryl O-Sulfamate Pharmacophore for Oncology and Women's Health.,  58  (19): [PMID:25992880] [10.1021/acs.jmedchem.5b00386]

15. Dasko M, Masyk M, Kubinski K, Aszyk J, Rachon J, Demkowicz S.  (2016)  Synthesis and steroid sulfatase inhibitory activities of N-phosphorylated 3-(4-aminophenyl)-coumarin-7-O-sulfamates,  7  (6): [10.1039/C6MD00113K]

16. Daśko M, Przybyłowska M, Rachon J, Masłyk M, Kubiński K, Misiak M, Składanowski A, Demkowicz S..  (2017)  Synthesis and biological evaluation of fluorinated N-benzoyl and N-phenylacetoyl derivatives of 3-(4-aminophenyl)-coumarin-7-O-sulfamate as steroid sulfatase inhibitors.,  128  [PMID:28152429] [10.1016/j.ejmech.2017.01.028]

17. Zaraei SO, Abduelkarem AR, Anbar HS, Kobeissi S, Mohammad M, Ossama A, El-Gamal MI..  (2019)  Sulfamates in drug design and discovery: Pre-clinical and clinical investigations.,  179  [PMID:31255926] [10.1016/j.ejmech.2019.06.052]

18. Biernacki K, Ciupak O, Daśko M, Rachon J, Kozak W, Rak J, Kubiński K, Masłyk M, Martyna A, Śliwka-Kaszyńska M, Wietrzyk J, Świtalska M, Nocentini A, Supuran CT, Demkowicz S..  (2022)  Development of Sulfamoylated 4-(1-Phenyl-1H-1,2,3-triazol-4-yl)phenol Derivatives as Potent Steroid Sulfatase Inhibitors for Efficient Treatment of Breast Cancer.,  65  (6.0): [PMID:35235747] [10.1021/acs.jmedchem.1c02220]

Source

Source(1):

• Scientific Literature