BRENDA - Enzyme Database show

Inhibition of steroid sulphatase activity by tricyclic coumarin sulphamates

Malini, B.; Purohit, A.; Ganeshapillai, D.; Woo, L.W.L.; Potter, B.V.L.; Reed, M.J.; J. Steroid Biochem. Mol. Biol. 75, 253-258 (2000)

Data extracted from this reference:

Application
EC Number
Application
Commentary
Organism
3.1.6.2
pharmacology
inhibition of STS is an important target for the development of new drugs for oncology and immunology
Rattus norvegicus
Inhibitors
EC Number
Inhibitors
Commentary
Organism
Structure
3.1.6.2
4-methylcoumarin-7-O-sulfamate
-
Rattus norvegicus
3.1.6.2
4-oxo-2,3-dihydro-1H-cyclopenta-[c][1]benzopyran-7-O-sulfamate
665 COUMATE, placental IC50: 200 nM
Rattus norvegicus
3.1.6.2
6-oxo-7,8,9,10,11,12,13,14,15,16-decahydro-cyclododeca-[c][1]benzopyran-3-O-sulfamate
6612 COUMATE, placental IC50: 60 nM
Rattus norvegicus
3.1.6.2
6-oxo-7,8,9,10,11,12,13,14-octahydro-cyclodeca-[c][1]benzopyran-3-O-sulfamate
6610 COUMATE, placental IC50: 1 nM
Rattus norvegicus
3.1.6.2
6-oxo-7,8,9,10,11,12-hexahydro-cycloocta-[c][1]benzopyran-3-O-sulfamate
668 COUMATE, placental IC50: 30 nM
Rattus norvegicus
3.1.6.2
6-oxo-7,8,9,10-tetrahydro-dibenzo[b,d]pyran-3-O-sulfamate
666 COUMATE, placental IC50: 70 nM
Rattus norvegicus
3.1.6.2
6-oxo-8,9,10,11,12,13,14,15,16,17,18,19-dodecahydro-7H-cyclopentadeca-[c][1]benzopyran-3-O-sulfamate
6615 COUMATE, placental IC50: 370 nM, most potent tricyclic coumarin sulfamate inhibitor tested in vivo
Rattus norvegicus
3.1.6.2
6-oxo-8,9,10,11,12,13,14,15,16,17-decahydro-7H-cyclotrideca-[c][1]benzopyran-3-O-sulfamate
6613 COUMATE, placental IC50: 75 nM
Rattus norvegicus
3.1.6.2
6-oxo-8,9,10,11,12,13,14,15-octahydro-7H-cycloundeca-[c][1]benzopyran-3-O-sulfamate
6611 COUMATE, placental IC50: 13 nM
Rattus norvegicus
3.1.6.2
6-oxo-8,9,10,11,12,13-hexahydro-7H-cyclonona-[c][1]benzopyran-3-O-sulfamate
669 COUMATE, placental IC50: 2.4 nM
Rattus norvegicus
3.1.6.2
6-oxo-8,9,10,11-tetrahydro-7H-cyclohepta-[c][1]benzopyran-3-O-sulfamate
667 COUMATE, placental IC50: 8 nM
Rattus norvegicus
3.1.6.2
tricyclic coumarin sulfamate
in vitro and in vivo inhibition studies with E1-STS from different tissues, structure-activity relationship of a number of tricyclic coumarin sulfamates, the size of the third ring has a marked effect on inhibitor potency
Rattus norvegicus
Localization
EC Number
Localization
Commentary
Organism
GeneOntology No.
Textmining
3.1.6.2
microsome
placental
Rattus norvegicus
-
-
Organism
EC Number
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
3.1.6.2
Rattus norvegicus
-
female Wistar rats
-
Source Tissue
EC Number
Source Tissue
Commentary
Organism
Textmining
3.1.6.2
brain
-
Rattus norvegicus
-
3.1.6.2
liver
-
Rattus norvegicus
-
3.1.6.2
placenta
-
Rattus norvegicus
-
3.1.6.2
white blood cell
-
Rattus norvegicus
-
Substrates and Products (Substrate)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
3.1.6.2
estrone sulfate + H2O
-
656639
Rattus norvegicus
estrone + sulfate
-
-
-
?
IC50 Value
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
3.1.6.2
0.000001
-
6610 COUMATE, placental IC50: 1 nM
Rattus norvegicus
6-oxo-7,8,9,10,11,12,13,14-octahydro-cyclodeca-[c][1]benzopyran-3-O-sulfamate
3.1.6.2
0.0000024
-
669 COUMATE, placental IC50: 2.4 nM
Rattus norvegicus
6-oxo-8,9,10,11,12,13-hexahydro-7H-cyclonona-[c][1]benzopyran-3-O-sulfamate
3.1.6.2
0.000008
-
667 COUMATE, placental IC50: 8 nM
Rattus norvegicus
6-oxo-8,9,10,11-tetrahydro-7H-cyclohepta-[c][1]benzopyran-3-O-sulfamate
3.1.6.2
0.000013
-
6611 COUMATE, placental IC50: 13 nM
Rattus norvegicus
6-oxo-8,9,10,11,12,13,14,15-octahydro-7H-cycloundeca-[c][1]benzopyran-3-O-sulfamate
3.1.6.2
0.00003
-
668 COUMATE, placental IC50: 30 nM
Rattus norvegicus
6-oxo-7,8,9,10,11,12-hexahydro-cycloocta-[c][1]benzopyran-3-O-sulfamate
3.1.6.2
0.00006
-
6612 COUMATE, placental IC50: 60 nM
Rattus norvegicus
6-oxo-7,8,9,10,11,12,13,14,15,16-decahydro-cyclododeca-[c][1]benzopyran-3-O-sulfamate
3.1.6.2
0.00007
-
666 COUMATE, placental IC50: 70 nM
Rattus norvegicus
6-oxo-7,8,9,10-tetrahydro-dibenzo[b,d]pyran-3-O-sulfamate
3.1.6.2
0.000075
-
6613 COUMATE, placental IC50: 75 nM
Rattus norvegicus
6-oxo-8,9,10,11,12,13,14,15,16,17-decahydro-7H-cyclotrideca-[c][1]benzopyran-3-O-sulfamate
3.1.6.2
0.0002
-
665 COUMATE, placental IC50: 200 nM
Rattus norvegicus
4-oxo-2,3-dihydro-1H-cyclopenta-[c][1]benzopyran-7-O-sulfamate
3.1.6.2
0.00037
-
6615 COUMATE, placental IC50: 370 nM, most potent tricyclic coumarin sulfamate inhibitor tested in vivo
Rattus norvegicus
6-oxo-8,9,10,11,12,13,14,15,16,17,18,19-dodecahydro-7H-cyclopentadeca-[c][1]benzopyran-3-O-sulfamate
Application (protein specific)
EC Number
Application
Commentary
Organism
3.1.6.2
pharmacology
inhibition of STS is an important target for the development of new drugs for oncology and immunology
Rattus norvegicus
IC50 Value (protein specific)
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
3.1.6.2
0.000001
-
6610 COUMATE, placental IC50: 1 nM
Rattus norvegicus
6-oxo-7,8,9,10,11,12,13,14-octahydro-cyclodeca-[c][1]benzopyran-3-O-sulfamate
3.1.6.2
0.0000024
-
669 COUMATE, placental IC50: 2.4 nM
Rattus norvegicus
6-oxo-8,9,10,11,12,13-hexahydro-7H-cyclonona-[c][1]benzopyran-3-O-sulfamate
3.1.6.2
0.000008
-
667 COUMATE, placental IC50: 8 nM
Rattus norvegicus
6-oxo-8,9,10,11-tetrahydro-7H-cyclohepta-[c][1]benzopyran-3-O-sulfamate
3.1.6.2
0.000013
-
6611 COUMATE, placental IC50: 13 nM
Rattus norvegicus
6-oxo-8,9,10,11,12,13,14,15-octahydro-7H-cycloundeca-[c][1]benzopyran-3-O-sulfamate
3.1.6.2
0.00003
-
668 COUMATE, placental IC50: 30 nM
Rattus norvegicus
6-oxo-7,8,9,10,11,12-hexahydro-cycloocta-[c][1]benzopyran-3-O-sulfamate
3.1.6.2
0.00006
-
6612 COUMATE, placental IC50: 60 nM
Rattus norvegicus
6-oxo-7,8,9,10,11,12,13,14,15,16-decahydro-cyclododeca-[c][1]benzopyran-3-O-sulfamate
3.1.6.2
0.00007
-
666 COUMATE, placental IC50: 70 nM
Rattus norvegicus
6-oxo-7,8,9,10-tetrahydro-dibenzo[b,d]pyran-3-O-sulfamate
3.1.6.2
0.000075
-
6613 COUMATE, placental IC50: 75 nM
Rattus norvegicus
6-oxo-8,9,10,11,12,13,14,15,16,17-decahydro-7H-cyclotrideca-[c][1]benzopyran-3-O-sulfamate
3.1.6.2
0.0002
-
665 COUMATE, placental IC50: 200 nM
Rattus norvegicus
4-oxo-2,3-dihydro-1H-cyclopenta-[c][1]benzopyran-7-O-sulfamate
3.1.6.2
0.00037
-
6615 COUMATE, placental IC50: 370 nM, most potent tricyclic coumarin sulfamate inhibitor tested in vivo
Rattus norvegicus
6-oxo-8,9,10,11,12,13,14,15,16,17,18,19-dodecahydro-7H-cyclopentadeca-[c][1]benzopyran-3-O-sulfamate
Inhibitors (protein specific)
EC Number
Inhibitors
Commentary
Organism
Structure
3.1.6.2
4-methylcoumarin-7-O-sulfamate
-
Rattus norvegicus
3.1.6.2
4-oxo-2,3-dihydro-1H-cyclopenta-[c][1]benzopyran-7-O-sulfamate
665 COUMATE, placental IC50: 200 nM
Rattus norvegicus
3.1.6.2
6-oxo-7,8,9,10,11,12,13,14,15,16-decahydro-cyclododeca-[c][1]benzopyran-3-O-sulfamate
6612 COUMATE, placental IC50: 60 nM
Rattus norvegicus
3.1.6.2
6-oxo-7,8,9,10,11,12,13,14-octahydro-cyclodeca-[c][1]benzopyran-3-O-sulfamate
6610 COUMATE, placental IC50: 1 nM
Rattus norvegicus
3.1.6.2
6-oxo-7,8,9,10,11,12-hexahydro-cycloocta-[c][1]benzopyran-3-O-sulfamate
668 COUMATE, placental IC50: 30 nM
Rattus norvegicus
3.1.6.2
6-oxo-7,8,9,10-tetrahydro-dibenzo[b,d]pyran-3-O-sulfamate
666 COUMATE, placental IC50: 70 nM
Rattus norvegicus
3.1.6.2
6-oxo-8,9,10,11,12,13,14,15,16,17,18,19-dodecahydro-7H-cyclopentadeca-[c][1]benzopyran-3-O-sulfamate
6615 COUMATE, placental IC50: 370 nM, most potent tricyclic coumarin sulfamate inhibitor tested in vivo
Rattus norvegicus
3.1.6.2
6-oxo-8,9,10,11,12,13,14,15,16,17-decahydro-7H-cyclotrideca-[c][1]benzopyran-3-O-sulfamate
6613 COUMATE, placental IC50: 75 nM
Rattus norvegicus
3.1.6.2
6-oxo-8,9,10,11,12,13,14,15-octahydro-7H-cycloundeca-[c][1]benzopyran-3-O-sulfamate
6611 COUMATE, placental IC50: 13 nM
Rattus norvegicus
3.1.6.2
6-oxo-8,9,10,11,12,13-hexahydro-7H-cyclonona-[c][1]benzopyran-3-O-sulfamate
669 COUMATE, placental IC50: 2.4 nM
Rattus norvegicus
3.1.6.2
6-oxo-8,9,10,11-tetrahydro-7H-cyclohepta-[c][1]benzopyran-3-O-sulfamate
667 COUMATE, placental IC50: 8 nM
Rattus norvegicus
3.1.6.2
tricyclic coumarin sulfamate
in vitro and in vivo inhibition studies with E1-STS from different tissues, structure-activity relationship of a number of tricyclic coumarin sulfamates, the size of the third ring has a marked effect on inhibitor potency
Rattus norvegicus
Localization (protein specific)
EC Number
Localization
Commentary
Organism
GeneOntology No.
Textmining
3.1.6.2
microsome
placental
Rattus norvegicus
-
-
Source Tissue (protein specific)
EC Number
Source Tissue
Commentary
Organism
Textmining
3.1.6.2
brain
-
Rattus norvegicus
-
3.1.6.2
liver
-
Rattus norvegicus
-
3.1.6.2
placenta
-
Rattus norvegicus
-
3.1.6.2
white blood cell
-
Rattus norvegicus
-
Substrates and Products (Substrate) (protein specific)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
3.1.6.2
estrone sulfate + H2O
-
656639
Rattus norvegicus
estrone + sulfate
-
-
-
?