Ligand all-trans-retinol

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Basic Ligand Information

Molecular Structure
Picture of all-trans-retinol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C20H30O
all-trans-retinol
FPIPGXGPPPQFEQ-OVSJKPMPSA-N
Synonyms:
all-tans-retinol, all-trans retinol, all trans retinol, retinol, retinol-[cellular-retinol-binding-protein], retinol-[cellular retinol-binding protein], Vitamin A

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (18 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
all-trans-retinol + NAD+ = all-trans-retinal + NADH
show the reaction diagram
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retinol + NAD+ + H2O = retinoic acid + NADH + H+
show the reaction diagram
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all-trans-retinol + reduced acceptor = all-trans-13,14-dihydroretinol + acceptor
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (14 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
all-trans retinal + NADPH + H+ = all-trans retinol + NADP+
show the reaction diagram
-
-
retinyl palmitate + H2O = retinol + palmitate
show the reaction diagram
-
retinyl-beta-glucuronide + H2O = retinol + D-glucuronide
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (65 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
all-trans-retinol + NADP+ = ? + NADPH
show the reaction diagram
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all-trans-retinol + NADP+ = all-trans-retinal + NADPH
show the reaction diagram
-
all-trans-retinol + NADP+ = all-trans-retinal + NADPH
show the reaction diagram
-
all-trans-retinol + NADP+ = all-trans-retinal + NADPH + H+
show the reaction diagram
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all-trans-retinol + 2 reduced adrenodoxin + 2 H+ + O2 = all-trans-3,4-didehydroretinol + 2 oxidized adrenodoxin + 2 H2O
show the reaction diagram
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retinol + NAD+ + H2O = retinoic acid + NADH + H+
show the reaction diagram
-
palmitoyl-CoA + all-trans-retinol = ?
show the reaction diagram
-
palmitoyl-CoA + all-trans-retinol = ?
show the reaction diagram
-
3'-phosphoadenylylsulfate + retinol = adenosine 3',5'-bisphosphate + retinol sulfate
show the reaction diagram
-
oleic acid + retinol = retinyl oleate
show the reaction diagram
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all-trans-retinol = 11-cis-retinol
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (39 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
retinal + NADPH = retinol + NADP+
show the reaction diagram
-
-
all-trans-retinal + NADPH + H+ = all-trans-retinol + NADP+
show the reaction diagram
-
-
all-trans-retinal + NADPH + H+ = all-tans-retinol + NADP+
show the reaction diagram
-
-
all-trans-retinal + NADP+ + H2O = all-trans-retinol + NADPH + H+
show the reaction diagram
-
-
retinyl palmitate + H2O = retinol + palmitate
show the reaction diagram
-
retinyl palmitate + H2O = retinol + palmitate
show the reaction diagram
-
retinyl palmitate + H2O = retinol + palmitate
show the reaction diagram
-
retinyl-beta-glucuronide + H2O = retinol + D-glucuronide
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
treatment of cultured Sertoli cells leads to activation of catalase by increasing its protein content, but without alteration of its mRNA expression. Retinol treatment also increases cell lipoperoxidation and intracellular reactive species production. All effects induced by retinol are inhibited by the antioxidant Trolox
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retinol activates tyrosine hydroxylase in vivo via two sequential non-genomic mechanisms: 1. retinol induces an influx in extracellular calcium, activation of protein kinase C and Ser40 phosphorylation, leading to tyrosine hydroxylase activation within 15 min, 2. the retinol-induced rise in intracellular calcium leads to an increase in reactive oxygen species, activation of extracellular signal-regulated kinase 1/2 and Ser31 phosphorylation and the maintenance of tyrosine hydroxylase activation for up to 2 h
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GNMT activity is induced by vitamin A
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Inhibitor in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
substrate inhibition
-
complete inhibition at 0.5 mM
-

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (18 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.02
-
37°C
0.01
-
pH 7.4
40.4
-
pH not specified in the publication, 20°C

KM Value (59 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.086
-
pH 7.4
0.02
-
-
0.4
-
pH 7.4, 37°C
0.003
-
-
0.0099
-
at pH 8.0 and 37°C

Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.475
-
at 37°C, in 50 mM Tris/HCl pH 7.6, 10 mM NH4Cl, 5 mM MgCl2, and 5 mM dithiothreitol

References & Links

Links to other databases for all-trans-retinol

ChEBI
PubChem
ChEBI
PubChem