Ligand rosmarinic acid

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Basic Ligand Information

Molecular Structure
Picture of rosmarinic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C18H16O8
rosmarinic acid
DOUMFZQKYFQNTF-WUTVXBCWSA-N
Synonyms:
rosmarinate, trans-rosmarinic acid

Roles as Enzyme Ligand

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
caffeoyl-CoA + 3-(3,4-dihydroxyphenyl)lactate = CoA + rosmarinate
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
rosmarinic acid + O2 = ?
show the reaction diagram
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N6-(2-isopentenyl)adenine + rosmarinic acid = adenine + 3-methylbut-2-enal + ?
show the reaction diagram
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S-adenosyl-L-methionine + rosmarinic acid = S-adenosyl-L-homocysteine + ?
show the reaction diagram
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rosmarinic acid + H2O = (2E)-3,4-dihydroxycinnamate + (2R)-3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-oxo-3-(3,4-dihydroxyphenyl)-propionate + H2 = rosmarinic acid
show the reaction diagram
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caffeoyl-CoA + 3-(3,4-dihydroxyphenyl)lactate = CoA + rosmarinate
show the reaction diagram
-

Inhibitor in Enzyme-catalyzed Reactions (23 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
docking structure with ALR2, overview
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strong inhibitor, at concentration higher than 0.2 mM, non-competitive
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40.2% inhibition at 0.1 mg/ml
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isoenzymes TAT-2 and TAT-3
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from extracts of Melissa officinalis leaves
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IC50 is 1.4 mM
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0.01 mg/ml, 55.2% inhibition
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inhibition of C5 convertase by binding to component C3b
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isolated from a methanolic extract of Argusia argentea (Boraginaceae) which significantly inhibits snake venom-induced hemorrhage; significantly inhibits the hemorrhagic effect of crude venom of Crotalus atrox and others as well as snake venom metalloproteinase HT-b
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binding to the enzyme involves residues Thr177, Ala178, Val179, Val218, and Ile245
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0.1 mM, 71.48% inhibition
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (2 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
109
-
-
0.4
-
pH 6.5, recombinant enzyme

KM Value (2 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.015
-
reverse reaction

Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.039
-
-

IC50 Value (13 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.125
-
at pH 7.4 and 37°C
1.4
-
IC50 is 1.4 mM

References & Links

Links to other databases for rosmarinic acid

ChEBI
PubChem
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PubChem