Record Information
Version1.0
Creation Date2016-09-30 22:48:09 UTC
Update Date2020-05-21 16:29:27 UTC
BMDB IDBMDB0001852
Secondary Accession Numbers
  • BMDB01852
Metabolite Identification
Common NameRetinoic acid
Descriptionall-trans-All-trans-all-all-trans-retinoic acid, also known as all-all-trans-retinoic acid or all-trans-retinoic acid, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. all-trans-All-trans-all-all-trans-retinoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. all-trans-All-trans-all-all-trans-retinoic acid participates in a number of enzymatic reactions, within cattle. In particular, all-trans-All-trans-all-all-trans-retinoic acid can be biosynthesized from vitamin a through the action of the enzyme retinal dehydrogenase 1. In addition, all-trans-All-trans-all-all-trans-retinoic acid can be biosynthesized from vitamin a; which is mediated by the enzyme retinal dehydrogenase 2. In cattle, all-trans-all-all-trans-retinoic acid is involved in the metabolic pathway called the retinol metabolism pathway. all-trans-All-trans-all-all-trans-retinoic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acidChEBI
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ecl)ChEBI
AGN 100335ChEBI
all-(e)-Retinoic acidChEBI
all-trans-beta-Retinoic acidChEBI
all-trans-TretinoinChEBI
all-trans-Vitamin a acidChEBI
all-trans-Vitamin a1 acidChEBI
beta-Retinoic acidChEBI
EudynaChEBI
RenovaChEBI
Retin-aChEBI
Retinoic acidChEBI
Retisol-aChEBI
Ro 1-5488ChEBI
SolageChEBI
Stieva-aChEBI
trans-Retinoic acidChEBI
Tretin mChEBI
TretinoinChEBI
VesanoidChEBI
Vitamin a acidChEBI
VitinoinChEBI
all-trans-RetinoateKegg
AvitaKegg
Retin aKegg
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoateGenerator
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoate (ecl)Generator
all-(e)-RetinoateGenerator
all-trans-b-RetinoateGenerator
all-trans-b-Retinoic acidGenerator
all-trans-beta-RetinoateGenerator
all-trans-Β-retinoateGenerator
all-trans-Β-retinoic acidGenerator
b-RetinoateGenerator
b-Retinoic acidGenerator
beta-RetinoateGenerator
Β-retinoateGenerator
Β-retinoic acidGenerator
RetinoateGenerator
trans-RetinoateGenerator
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoateHMDB
Tretinoin zinc saltHMDB
trans Retinoic acidHMDB
Acid, all-trans-retinoicHMDB
Salt, tretinoin sodiumHMDB
beta all trans Retinoic acidHMDB
beta-all-trans-Retinoic acidHMDB
Acid, vitamin aHMDB
Potassium salt, tretinoinHMDB
Sodium salt, tretinoinHMDB
Acid, beta-all-trans-retinoicHMDB
Tretinoin potassium saltHMDB
Zinc salt, tretinoinHMDB
Acid, retinoicHMDB
Acid, trans-retinoicHMDB
Salt, tretinoin potassiumHMDB
Salt, tretinoin zincHMDB
Tretinoin sodium saltHMDB
all trans Retinoic acidHMDB
Retin-a microHMDB
AtralinHMDB
Tretin-XHMDB
all-trans-Retinoic acidMeSH
Chemical FormulaC20H28O2
Average Molecular Weight300.442
Monoisotopic Molecular Weight300.208930142
IUPAC Name(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
Traditional Nametretinoin
CAS Registry Number302-79-4
SMILES
C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
InChI Identifier
InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+
InChI KeySHGAZHPCJJPHSC-YCNIQYBTSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassRetinoids
Direct ParentRetinoids
Alternative Parents
Substituents
  • Retinoic acid
  • Diterpenoid
  • Retinoid skeleton
  • Medium-chain fatty acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Fatty acyl
  • Unsaturated fatty acid
  • Fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Myelin sheath
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.66ALOGPS
logP5.01ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.79 m³·mol⁻¹ChemAxon
Polarizability36.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-2090000000-db078f48efb8038384f2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0009000000-12dbd83959268dee6dbfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-066r-4900000000-31c9262cbbf0bad5b738View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fsl-9600000000-c6681587f0a9ae7a712eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0mc0-4941000000-401db468e6db7c5bbb5aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-0090000000-d05c305f987a713dfaa0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0239000000-09da873ecbe1e09a1602View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-dca272cadb8a3ba3f819View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-016r-9630000000-553ddaf9452713df67eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0390000000-241af7f979164ecfbf34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0mc0-4941000000-05bed4117d9ed953a2caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-9400000000-3ecfeb7f6c8384d2a0d3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0239000000-2c6852256fcbebe1a2aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-0910000000-a1c1aa8b35e78558cd5bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uei-0494000000-28e6366fdd47e8ba2117View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-2980000000-3e7fc78de83c23830416View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-5900000000-ef4d86f8bcf86959f794View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052b-0090000000-e07ffb4c1e5c63ab1b59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-0090000000-a0a8411213bbd2543243View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3690000000-97e6a74798dd69c30ad1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zir-0973000000-3040e9e4a1a5448efbcbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-060c-1950000000-f3b9c9b378f60b8c49a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar3-5910000000-de22eb65f274483f3f98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052b-0090000000-5f942e3b870e7bd0121bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0190000000-22b445382d3977280045View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-4900000000-0005b37f6d54a42a84f6View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Myelin sheath
  • Nucleus
Biospecimen Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Lung
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate Tissue
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Adrenal CortexExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Adrenal GlandExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BladderExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LungExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PancreasExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001852
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022710
KNApSAcK IDNot Available
Chemspider ID392618
KEGG Compound IDC00777
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTretinoin
METLIN IDNot Available
PubChem Compound444795
PDB IDNot Available
ChEBI ID15367
References
Synthesis ReferenceSolladie, Guy; Girardin, Andre. Highly stereoselective synthesis of vitamin A and all-trans retinoic acid by low-valent titanium induced reductive elimination. Tetrahedron Letters (1988), 29(2), 213-16.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A28
Uniprot ID:
P79102
Molecular weight:
58152.0
Reactions
Retinoic acid → all-trans-5,6-Epoxyretinoic aciddetails
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase involved in the metabolism of fatty acids. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates fatty acids specifically at the omega-1 position displaying the highest catalytic activity for saturated fatty acids. May be involved in the oxidative metabolism of xenobiotics.
Gene Name:
CYP2E1
Uniprot ID:
O18963
Molecular weight:
56827.0
Reactions
Retinoic acid → all-trans-5,6-Epoxyretinoic aciddetails
General function:
Involved in prostaglandin-D synthase activity
Specific function:
Catalyzes the conversion of PGH2 to PGD2, a prostaglandin involved in smooth muscle contraction/relaxation and a potent inhibitor of platelet aggregation. Involved in a variety of CNS functions, such as sedation, NREM sleep and PGE2-induced allodynia, and may have an anti-apoptotic role in oligodendrocytes. Binds small non-substrate lipophilic molecules, including biliverdin, bilirubin, retinal, retinoic acid and thyroid hormone, and may act as a scavenger for harmful hydrophobic molecules and as a secretory retinoid and thyroid hormone transporter. Possibly involved in development and maintenance of the blood-brain, blood-retina, blood-aqueous humor and blood-testis barrier. It is likely to play important roles in both maturation and maintenance of the central nervous system and male reproductive system (By similarity).
Gene Name:
PTGDS
Uniprot ID:
O02853
Molecular weight:
21229.0
General function:
Energy production and conversion
Specific function:
Can convert/oxidize retinaldehyde to retinoic acid. Binds free retinal and cellular retinol-binding protein-bound retinal. May have a broader specificity and oxidize other aldehydes in vivo.
Gene Name:
ALDH1A1
Uniprot ID:
P48644
Molecular weight:
54806.0
Reactions
Vitamin A + NAD + Water → Retinoic acid + NADHdetails
General function:
Transcription
Specific function:
Component of the Polycomb group (PcG) multiprotein BCOR complex, a complex required to maintain the transcriptionally repressive state of some genes, such as BCL6 and the cyclin-dependent kinase inhibitor, CDKN1A. Transcriptional repressor that may be targeted to the DNA by BCL6; this transcription repressor activity may be related to PKC signaling pathway. Represses CDKN1A expression by binding to its promoter, and this repression is dependent on the retinoic acid response element (RARE element). Promotes cell cycle progression and enhances cell proliferation as well. May have a positive role in tumor cell growth by down-regulating CDKN1A. Component of a Polycomb group (PcG) multiprotein PRC1-like complex, a complex class required to maintain the transcriptionally repressive state of many genes, including Hox genes, throughout development. PcG PRC1 complex acts via chromatin remodeling and modification of histones; it mediates monoubiquitination of histone H2A 'Lys-119', rendering chromatin heritably changed in its expressibility. Within the PRC1-like complex, regulates RNF2 ubiquitin ligase activity. Regulates the expression of DPPA4 and NANOG in the NT2 embryonic carcinoma cells.
Gene Name:
PCGF1
Uniprot ID:
Q2YDF9
Molecular weight:
30324.0
General function:
Involved in receptor activity
Specific function:
Not Available
Gene Name:
RARRES1
Uniprot ID:
Q0P5D6
Molecular weight:
32771.0
General function:
Involved in retinoic acid receptor activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q45UD6
Molecular weight:
10459.0
General function:
Not Available
Specific function:
Adipocyte-secreted protein (adipokine) that regulates adipogenesis, metabolism and inflammation through activation of the chemokine-like receptor 1 (CMKLR1). Its other ligands include G protein-coupled receptor 1 (GPR1) and chemokine receptor-like 2 (CCRL2). Positively regulates adipocyte differentiation, modulates the expression of adipocyte genes involved in lipid and glucose metabolism and might play a role in angiogenesis, a process essential for the expansion of white adipose tissue. Also acts as a proinflammatory adipokine, causing an increase in secretion of proinflammatory and prodiabetic adipokines, which further impair adipose tissue metabolic function and have negative systemic effects including impaired insulin sensitivity, altered glucose and lipid metabolism, and a decrease in vascular function in other tissues. Can have both pro- and anti-inflammatory properties depending on the modality of enzymatic cleavage by different classes of proteases. Acts as a chemotactic factor for leukocyte populations expressing CMKLR1, particularly immature plasmacytoid dendritic cells, but also immature myeloid DCs, macrophages and natural killer cells. Exerts an anti-inflammatory role by preventing TNF/TNFA-induced VCAM1 expression and monocytes adhesion in vascular endothelial cells. The effect is mediated via inhibiting activation of NF-kappa-B and CRK/p38 through stimulation of AKT1/NOS3 signaling and nitric oxide production. Exhibits an antimicrobial function in the skin (By similarity).
Gene Name:
RARRES2
Uniprot ID:
Q29RS5
Molecular weight:
18357.0
General function:
Involved in retinoic acid receptor activity
Specific function:
Not Available
Gene Name:
RARA
Uniprot ID:
Q58DG3
Molecular weight:
30654.0
General function:
Involved in retinoic acid receptor activity
Specific function:
Not Available
Gene Name:
RARG
Uniprot ID:
Q08DD4
Molecular weight:
50946.0
General function:
Involved in protein binding
Specific function:
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels.
Gene Name:
PPARG
Uniprot ID:
O18971
Molecular weight:
57579.0
General function:
Involved in lipid binding
Specific function:
Lipid transport protein in adipocytes. Binds both long chain fatty acids and retinoic acid. Delivers long-chain fatty acids and retinoic acid to their cognate receptors in the nucleus.
Gene Name:
FABP4
Uniprot ID:
P48035
Molecular weight:
14678.0
General function:
Involved in retinal binding
Specific function:
Cytosolic CRABPs may regulate the access of retinoic acid to the nuclear retinoic acid receptors.
Gene Name:
CRABP1
Uniprot ID:
P62964
Molecular weight:
15592.0
General function:
Involved in SMAD binding
Specific function:
Not Available
Gene Name:
LOC100138545
Uniprot ID:
A6QQE3
Molecular weight:
91118.0
General function:
Involved in steroid binding
Specific function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. The high affinity ligand for RXRs is 9-cis retinoic acid (By similarity).
Gene Name:
RXRG
Uniprot ID:
Q0VC20
Molecular weight:
50882.0
General function:
Involved in retinal binding
Specific function:
Transports retinoic acid to the nucleus. Regulates the access of retinoic acid to the nuclear retinoic acid receptors (By similarity).
Gene Name:
CRABP2
Uniprot ID:
Q5PXY7
Molecular weight:
15735.0
General function:
Not Available
Specific function:
Involved in the metabolism of retinoic acid (RA), rendering this classical morphogen inactive through oxidation. Involved in the specific inactivation of all-trans-retinoic acid (all-trans-RA), with a preference for the following substrates: all-trans-RA > 9-cis-RA > 13-cis-RA. Generates several hydroxylated forms of RA, including 4-OH-RA, 4-oxo-RA, and 18-OH-RA. Essential for postnatal survival. Plays a central role in germ cell development: acts by degrading RA in the developing testis, preventing STRA8 expression, thereby leading to delay of meiosis. Required for the maintenance of the undifferentiated state of male germ cells during embryonic development in Sertoli cells, inducing arrest in G0 phase of the cell cycle and preventing meiotic entry. Plays a role in skeletal development, both at the level of patterning and in the ossification of bone and the establishment of some synovial joints (By similarity).
Gene Name:
CYP26B1
Uniprot ID:
E1BHJ4
Molecular weight:
57414.0
Reactions
Retinoic acid → 4-Hydroxyretinoic aciddetails
Retinoic acid → all-trans-18-Hydroxyretinoic aciddetails