BRENDA - Enzyme Database show

Tetra- and pentacyclic triterpene acids from the ancient anti-inflammatory remedy frankincense as inhibitors of microsomal prostaglandin E2 synthase-1

Verhoff, M.; Seitz, S.; Paul, M.; Noha, S.M.; Jauch, J.; Schuster, D.; Werz, O.; J. Nat. Prod. 77, 1445-1451 (2014)

Data extracted from this reference:

Inhibitors
EC Number
Inhibitors
Commentary
Organism
Structure
5.3.99.3
11-oxo-beta-boswellic acid
-
Homo sapiens
5.3.99.3
3-O-acetyl-28-hydroxylupeolic acid
31.1% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
3-O-acetyllupeolic acid
51.4% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
3-O-acteyl-11-oxo-beta-boswellic acid
-
Homo sapiens
5.3.99.3
3-O-acteyl-beta-boswellic acid
-
Homo sapiens
5.3.99.3
3-oxo-8,24-dienetirucallic acid
16.7% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
3alpha-acetoxy-7,24-dienetirucallic acid
20.6% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
3alpha-acetoxy-8,24-dienetirucallic acid
36.8% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
3alpha-hydroxy-7,24-dienetirucallic acid
29.6% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
3alpha-hydroxy-8,24-dienetirucallic acid
3.5% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
3beta-hydroxy-8,24-dienetirucallic acid
29.2% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
4,(23)-dihydro-11-oxo-roburic acid
21.6% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
4,(23)-dihydronyctanthic acid
74.1% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
4,(23)-dihydroroburic acid
92.4% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
beta-boswellic acid
-
Homo sapiens
5.3.99.3
lupeolic acid
43.1% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
roburic acid
83.9% residual activity at 0.01 mM
Homo sapiens
Localization
EC Number
Localization
Commentary
Organism
GeneOntology No.
Textmining
5.3.99.3
microsome
-
Homo sapiens
-
-
Natural Substrates/ Products (Substrates)
EC Number
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
5.3.99.3
Prostaglandin H2
Homo sapiens
-
Prostaglandin E2
-
-
?
Organism
EC Number
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
5.3.99.3
Homo sapiens
-
-
-
Source Tissue
EC Number
Source Tissue
Commentary
Organism
Textmining
5.3.99.3
A-549 cell
-
Homo sapiens
-
Substrates and Products (Substrate)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
5.3.99.3
Prostaglandin H2
-
748441
Homo sapiens
Prostaglandin E2
-
-
-
?
IC50 Value
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
5.3.99.3
0.0004
-
at pH 7.4 and 4C
Homo sapiens
3alpha-acetoxy-7,24-dienetirucallic acid
5.3.99.3
0.0004
-
at pH 7.4 and 4C
Homo sapiens
3alpha-acetoxy-8,24-dienetirucallic acid
5.3.99.3
0.0009
-
at pH 7.4 and 4C
Homo sapiens
3-O-acetyl-28-hydroxylupeolic acid
5.3.99.3
0.0009
-
at pH 7.4 and 4C
Homo sapiens
3-oxo-8,24-dienetirucallic acid
5.3.99.3
0.001
-
at pH 7.4 and 4C
Homo sapiens
4,(23)-dihydro-11-oxo-roburic acid
5.3.99.3
0.0011
-
at pH 7.4 and 4C
Homo sapiens
3alpha-hydroxy-8,24-dienetirucallic acid
5.3.99.3
0.0012
-
at pH 7.4 and 4C
Homo sapiens
3beta-hydroxy-8,24-dienetirucallic acid
5.3.99.3
0.003
-
at pH 7.4 and 4C
Homo sapiens
3alpha-hydroxy-7,24-dienetirucallic acid
5.3.99.3
0.0085
-
at pH 7.4 and 4C
Homo sapiens
lupeolic acid
5.3.99.3
0.01
-
at pH 7.4 and 4C
Homo sapiens
3-O-acetyllupeolic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, at pH 7.4 and 4C
Homo sapiens
4,(23)-dihydronyctanthic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, at pH 7.4 and 4C
Homo sapiens
4,(23)-dihydroroburic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, at pH 7.4 and 4C
Homo sapiens
roburic acid
IC50 Value (protein specific)
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
5.3.99.3
0.0004
-
at pH 7.4 and 4C
Homo sapiens
3alpha-acetoxy-7,24-dienetirucallic acid
5.3.99.3
0.0004
-
at pH 7.4 and 4C
Homo sapiens
3alpha-acetoxy-8,24-dienetirucallic acid
5.3.99.3
0.0009
-
at pH 7.4 and 4C
Homo sapiens
3-O-acetyl-28-hydroxylupeolic acid
5.3.99.3
0.0009
-
at pH 7.4 and 4C
Homo sapiens
3-oxo-8,24-dienetirucallic acid
5.3.99.3
0.001
-
at pH 7.4 and 4C
Homo sapiens
4,(23)-dihydro-11-oxo-roburic acid
5.3.99.3
0.0011
-
at pH 7.4 and 4C
Homo sapiens
3alpha-hydroxy-8,24-dienetirucallic acid
5.3.99.3
0.0012
-
at pH 7.4 and 4C
Homo sapiens
3beta-hydroxy-8,24-dienetirucallic acid
5.3.99.3
0.003
-
at pH 7.4 and 4C
Homo sapiens
3alpha-hydroxy-7,24-dienetirucallic acid
5.3.99.3
0.0085
-
at pH 7.4 and 4C
Homo sapiens
lupeolic acid
5.3.99.3
0.01
-
at pH 7.4 and 4C
Homo sapiens
3-O-acetyllupeolic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, at pH 7.4 and 4C
Homo sapiens
4,(23)-dihydronyctanthic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, at pH 7.4 and 4C
Homo sapiens
4,(23)-dihydroroburic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, at pH 7.4 and 4C
Homo sapiens
roburic acid
Inhibitors (protein specific)
EC Number
Inhibitors
Commentary
Organism
Structure
5.3.99.3
11-oxo-beta-boswellic acid
-
Homo sapiens
5.3.99.3
3-O-acetyl-28-hydroxylupeolic acid
31.1% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
3-O-acetyllupeolic acid
51.4% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
3-O-acteyl-11-oxo-beta-boswellic acid
-
Homo sapiens
5.3.99.3
3-O-acteyl-beta-boswellic acid
-
Homo sapiens
5.3.99.3
3-oxo-8,24-dienetirucallic acid
16.7% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
3alpha-acetoxy-7,24-dienetirucallic acid
20.6% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
3alpha-acetoxy-8,24-dienetirucallic acid
36.8% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
3alpha-hydroxy-7,24-dienetirucallic acid
29.6% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
3alpha-hydroxy-8,24-dienetirucallic acid
3.5% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
3beta-hydroxy-8,24-dienetirucallic acid
29.2% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
4,(23)-dihydro-11-oxo-roburic acid
21.6% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
4,(23)-dihydronyctanthic acid
74.1% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
4,(23)-dihydroroburic acid
92.4% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
beta-boswellic acid
-
Homo sapiens
5.3.99.3
lupeolic acid
43.1% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
roburic acid
83.9% residual activity at 0.01 mM
Homo sapiens
Localization (protein specific)
EC Number
Localization
Commentary
Organism
GeneOntology No.
Textmining
5.3.99.3
microsome
-
Homo sapiens
-
-
Natural Substrates/ Products (Substrates) (protein specific)
EC Number
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
5.3.99.3
Prostaglandin H2
Homo sapiens
-
Prostaglandin E2
-
-
?
Source Tissue (protein specific)
EC Number
Source Tissue
Commentary
Organism
Textmining
5.3.99.3
A-549 cell
-
Homo sapiens
-
Substrates and Products (Substrate) (protein specific)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
5.3.99.3
Prostaglandin H2
-
748441
Homo sapiens
Prostaglandin E2
-
-
-
?