Ligand palmitoleic acid

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Basic Ligand Information

Molecular Structure
Picture of palmitoleic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C16H30O2
palmitoleic acid
KVJXBPDAXMEYOA-CXANFOAXSA-N
Synonyms:
(9Z)-hexadec-9-enoate, (9Z)-hexadec-9-enoic acid, (9Z)-hexadecenoate, (9Z)-hexadecenoic acid, (Z)-9-hexadecenoic acid, 9-cis-hexadecenoic acid, cis-9-hexadecenoic acid, hexadecenoate, palmitoleate, palmitoleoate


Show all pahtways known for Show all BRENDA pathways known for palmitoleic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
palmitoleic acid + reduced acceptor + O2 = (9Z,12Z)-hexadeca-9,12-dienoic acid + acceptor + H2O
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
[Wnt]-O-(9Z)-hexadec-9-enoyl-L-serine + H2O = [Wnt]-L-serine + (9Z)-hexadec-9-enoate
show the reaction diagram
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palmitoleoyl-CoA + H2O = CoA + palmitoleate
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (25 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
9-cis-hexadecenoic acid + cumene hydroperoxide = 9,10-epoxy hexadecanoic acid + ?
show the reaction diagram
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palmitoleate + O2 = 8-hydroperoxy-9(Z)-hexadecenoic acid
show the reaction diagram
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palmitoleate + ferrocytochrome P-450 + H+ + O2 = 12-hydroxypalmitoleate + ferricytochrome P-450 + H2O
show the reaction diagram
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palmitoleic acid + ferrocytochrome b5 + O2 + H+ = ?
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(9Z)-hexadecenoate + 2 ferrocytochrome b5 + O2 + 2 H+ = (9Z,12E)-hexadeca-9,12-dienoate + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
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palmitoleate + O2 = (9Z)-5,8-dihydroxyhexadeca-9-enoic acid
show the reaction diagram
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ATP + palmitoleic acid + [acyl-carrier protein] = AMP + diphosphate + palmitoleoyl-[acyl-carrier protein]
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Product in Enzyme-catalyzed Reactions (22 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
cis-9-hexadecenal + NAD+ + H2O = cis-9-hexadecenoic acid + NADH
show the reaction diagram
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(Z)-9-hexadecenal + H2O + O2 = (Z)-9-hexadecenoic acid + H2O2
show the reaction diagram
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monopalmitoin + H2O = glycerol + palmitoleic acid
show the reaction diagram
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[Wnt]-O-(9Z)-hexadec-9-enoyl-L-serine + H2O = [Wnt]-L-serine + (9Z)-hexadec-9-enoate
show the reaction diagram
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palmitoleamide + H2O = palmitoleic acid + NH3
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
137% of the activitation with palmitic acid
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approx. 4fold activiation
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stimulation of dephosphorylation of phosphorylated myelin basic protein but not phosphorylated casein
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Inhibitor in Enzyme-catalyzed Reactions (12 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.31 mM, 50% inhibition, synergism with cis-9,10-methylenehexadecanoic acid
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IC50: 0.095 mM
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IC50: 0.405 mM
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72% inhibition at 0.02 mM
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3D Structure of Enzyme-Ligand-Complex (PDB) (100 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (8 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
22.8
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CYP102A7, at pH 7.5
4.86
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recombinant enzyme, whole enzyme activity, pH 6.5, 40°C

KM Value (13 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0165
-
CYP102A7, at pH 7.5
0.048
-
recombinant enzyme, whole enzyme activity, pH 6.5, 40°C

Ki Value (2 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0098
-
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0.0037
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at pH 7.6 and 25°C

IC50 Value (2 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.095
-
IC50: 0.095 mM
0.405
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IC50: 0.405 mM

References & Links

Links to other databases for palmitoleic acid

ChEBI
PubChem
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PubChem