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BRENDA support

Ligand all-trans-retinoic acid

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Basic Ligand Information

Molecular Structure
Picture of all-trans-retinoic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C20H28O2
all-trans-retinoic acid
SHGAZHPCJJPHSC-YCNIQYBTSA-N
Synonyms:
all-trans-retinoate, all-trans retinoate, all-trans retinoic acid, retinoate, retinoic acid, tretinoin

Roles as Enzyme Ligand

In Vivo Product in Enzyme-catalyzed Reactions (13 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE

Substrate in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
all-trans-retinoic acid + 2 reduced adrenodoxin + 2 H+ + O2 = all-trans-3,4-didehydroretinoic acid + 2 oxidized adrenodoxin + 2 H2O
show the reaction diagram
-
UDP-glucuronate + all-trans-retinoic acid = UDP + all-trans-retinoic acid beta-D-glucuronoside
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (34 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
retinal + NAD+ = retinoic acid + NADH + H+
show the reaction diagram
-

Activator in Enzyme-catalyzed Reactions (27 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.001 mM, significant stimulation of the conversion of estradiol to estrone in the MCF-7 cell line and MDA-MB-231 cell line, 0.0001 mM has no effect
-
retinoic acid (100 nM and 0.001 mM) increases CAT activity after 24 h of treatment
-
induction of isozyme type III from brain astrocytes
-
up-regulates enzyme activity in embryonic carcinoma cell ine PCC7-Mz1
-
activation
-
upregulation of enzyme expression, synergistic with interleukin-4 in activating the core 4 N-acetylglucosaminyltransferase activity
-
treatment of cells induces increase in ornithine aminotransferase expression and activity which results in decreased intracellular concentrations of ornithine and polyamines putrescine, spermidine and spermine. Changes occur concomitantly with a decrease in the total number of cells, and the increase in ornithine aminotransferase activity is due to increased mRNA expression. In cells treated with 1 microM retinoic acid, addition of 10 microM putrescine to culture medium restores both cellular levels of polyamines and cell numbers to the values for the control group
-
upregulation of GALNAC4S-6ST
-
all-trans retinoic acid, ATRA, increases the expression of ACER2 in HeLa cells
-
ATRA
-

Inhibitor in Enzyme-catalyzed Reactions (16 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
weak feedback inhibition
-
suppresses the upregulation by vitamin A deficiency
-
docking energy level (Kcal/mol): -12.1034
-
after 6 days of retinoid exposure, cutaneous transcripts arising from Cyp4f13, 4f14, and 4f37 are down-regulated. No changes in transcript abundance for the Cyp4f16, 4f17, and 4f18 genes
-
0.005 mM, 56% reduction of activity
-
20% decrease of N-acetyl-S-(E,E)-farnesyl-L-cysteine methylation in cells treated with 0.01 mM retinoic acid
-
inhibits ceramide kinase transkription in neuroblastoma cells
-
IC50 value below 250 microM, Hill coefficient between 0.5 and 1.5
-
1 microM suppresses histidase expression almost completely, levels of histidase mRNA expression in the presence of all-trans retinoic acid are significantly lower on day 2 of post-confluence and at all later time points during keratinocyte differentiation
-

3D Structure of Enzyme-Ligand-Complex (PDB) (3 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (1 result)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.023
-
pH 7.4, temperature not specified in the publication

KM Value (1 result)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.00087
-
pH 7.4, temperature not specified in the publication

Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.015
-
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-retinoic acid

ChEBI
PubChem
ChEBI
PubChem