Record Information
Version1.0
Creation Date2016-09-30 22:44:40 UTC
Update Date2020-05-21 16:29:06 UTC
BMDB IDBMDB0001358
Secondary Accession Numbers
  • BMDB01358
Metabolite Identification
Common NameRetinal
Description13-cis-13-cis-13-cis-retinal, also known as 13Z-13-cis-retinal or 13-cis-retinal, 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. Thus, 13-cis-13-cis-retinal is considered to be an isoprenoid lipid molecule. 13-cis-13-cis-13-cis-retinal is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 13-cis-13-cis-13-cis-retinal exists in all living organisms, ranging from bacteria to humans. In cattle, 13-cis-13-cis-retinal is involved in the metabolic pathway called the retinol metabolism pathway.
Structure
Thumb
Synonyms
ValueSource
all-trans-RetinaldehydeChEBI
all-trans-RetineneChEBI
all-trans-Vitamin a aldehydeChEBI
RetinaldehydeChEBI
RetineneChEBI
Vitamin a aldehydeChEBI
all-trans-RetinalKegg
Aldehyde, vitamin aHMDB
AxerophthalHMDB
11 cis RetinalHMDB
11-cis-RetinalHMDB
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenalHMDB
all-e-RetinalHMDB
all-epsilon-RetinalHMDB
alpha-RetineneHMDB
e-RetinalHMDB
epsilon-RetinalHMDB
Retinene 1HMDB
trans-RetinalHMDB
trans-Vitamin a aldehydeHMDB
Vitamin a1 aldehydeHMDB
Chemical FormulaC20H28O
Average Molecular Weight284.4357
Monoisotopic Molecular Weight284.214015518
IUPAC Name(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal
Traditional Nameretinaldehyde
CAS Registry Number116-31-4
SMILES
C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=O
InChI Identifier
InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
InChI KeyNCYCYZXNIZJOKI-OVSJKPMPSA-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
  • Retinoid skeleton
  • Diterpenoid
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Myelin sheath
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point63 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.62ALOGPS
logP4.86ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity96.87 m³·mol⁻¹ChemAxon
Polarizability35.69 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, Positivesplash10-014i-2290000000-df9d2aa7545cc60a54f9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-9700000000-c2e22000dfae0765c367View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03g0-0950000000-bccf87de037f98873f41View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-01t9-1910000000-5fe7643c395769c68286View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-9700000000-fca532f917595376d653View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0490000000-f543f08fbaf94a2e3f8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3940000000-74f087cc812b3715e7acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fri-9830000000-72a5d01c6181340ad986View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-bad35938b77f181c29b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-1aadad0770df07f98436View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ko-4690000000-f624d342f88456375b9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00n3-1960000000-43f8c66f164764c37361View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0609-3920000000-dbeab0a82b306761cf6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-7900000000-d2bb7c1aeeb87d8833d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a59-0090000000-2ec2f8f314943441fa15View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0190000000-312cebb17ccd0189ab4dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1590000000-b2551eac481c0c930a4dView 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
  • Membrane
  • Myelin sheath
Biospecimen Locations
  • Adrenal Cortex
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Lung
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adrenal CortexExpected 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
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
Skeletal MuscleExpected 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 IDHMDB0001358
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022576
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00376
BioCyc IDRETINAL
BiGG IDNot Available
Wikipedia LinkRetinal
METLIN IDNot Available
PubChem Compound638015
PDB IDNot Available
ChEBI ID17898
References
Synthesis ReferenceDuhamel, Lucette; Duhamel, Pierre; Lecouve, Jean Pierre. A new synthesis of retinals. Journal of Chemical Research, Synopses (1986), (1), 34-5.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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
General function:
Lipid transport and metabolism
Specific function:
NAD-dependent oxidoreductase with broad substrate specificity that shows both oxidative and reductive activity (in vitro). Has 17-beta-hydroxysteroid dehydrogenase activity towards various steroids (in vitro). Converts 5-alpha-androstan-3-alpha,17-beta-diol to androsterone and estradiol to estrone (in vitro). Has 3-alpha-hydroxysteroid dehydrogenase activity towards androsterone (in vitro). Has retinol dehydrogenase activity towards all-trans-retinol (in vitro). Can convert androsterone to epi-androsterone. Androsterone is first oxidized to 5-alpha-androstane-3,17-dione and then reduced to epi-andosterone. Can act on both C-19 and C-21 3-alpha-hydroxysteroids (By similarity).
Gene Name:
HSD17B6
Uniprot ID:
Q3T001
Molecular weight:
36198.0
General function:
Lipid transport and metabolism
Specific function:
Retinol dehydrogenase with a clear preference for NADP. Converts all-trans-retinal to all-trans-retinol. May play a role in the regeneration of visual pigment at high light intensity.
Gene Name:
RDH8
Uniprot ID:
Q9N126
Molecular weight:
33956.0
Reactions
11-cis-Retinaldehyde + NADP → Retinal + NADPHdetails
General function:
Lipid transport and metabolism
Specific function:
Catalyzes the oxidation of cis-isomers of retinol, including 11-cis-, 9-cis-, and 13-cis-retinol in an NAD-dependent manner (PubMed:7544779, PubMed:7836368, PubMed:9654122). Has no activity towards all-trans retinal (PubMed:9654122). Plays a significant role in 11-cis retinol oxidation in the retinal pigment epithelium cells (RPE) (By similarity). Also recognizes steroids (androsterone, androstanediol) as its substrates (By similarity).
Gene Name:
RDH5
Uniprot ID:
Q27979
Molecular weight:
35037.0
General function:
Lipid transport and metabolism
Specific function:
Retinol dehydrogenase with a clear preference for NADP. Converts all-trans-retinol to all-trans-retinal. Has no detectable activity towards 11-cis-retinol, 9-cis-retinol and 13-cis-retinol (By similarity).
Gene Name:
RDH10
Uniprot ID:
Q8HZT6
Molecular weight:
38087.0
General function:
Energy production and conversion
Specific function:
Catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione. Also oxidizes long chain omega-hydroxy fatty acids, such as 20-HETE, producing both the intermediate aldehyde, 20-oxoarachidonate and the end product, a dicarboxylic acid, (5Z,8Z,11Z,14Z)-eicosatetraenedioate. Class-III ADH is remarkably ineffective in oxidizing ethanol.
Gene Name:
ADH5
Uniprot ID:
Q3ZC42
Molecular weight:
39677.0
Reactions
11-cis-Retinaldehyde + NAD → Retinal + NADHdetails
General function:
Lipid transport and metabolism
Specific function:
Retinoids dehydrogenase/reductase with a clear preference for NADP. Displays high activity towards 9-cis, 11-cis and all-trans-retinal. Shows very weak activity towards 13-cis-retinol. Also exhibits activity, albeit with lower affinity than for retinaldehydes, towards lipid peroxidation products (C9 aldehydes) such as 4-hydroxynonenal and trans-2-nonenal. May play an important function in photoreceptor cells to detoxify 4-hydroxynonenal and potentially other toxic aldehyde products resulting from lipid peroxidation. Has no dehydrogenase activity towards steroids.
Gene Name:
RDH12
Uniprot ID:
P59837
Molecular weight:
35171.0
Reactions
11-cis-Retinaldehyde → Retinaldetails
Vitamin A + NADP → Retinal + NADPHdetails
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Critical isomerohydrolase in the retinoid cycle involved in regeneration of 11-cis-retinal, the chromophore of rod and cone opsins. Catalyzes the cleavage and isomerization of all-trans-retinyl fatty acid esters to 11-cis-retinol which is further oxidized by 11-cis retinol dehydrogenase to 11-cis-retinal for use as visual chromophore (PubMed:16096063, PubMed:19805034, PubMed:20100834). Essential for the production of 11-cis retinal for both rod and cone photoreceptors. Also capable of catalyzing the isomerization of lutein to meso-zeaxanthin an eye-specific carotenoid (By similarity). The soluble form binds vitamin A (all-trans-retinol), making it available for LRAT processing to all-trans-retinyl ester. The membrane form, palmitoylated by LRAT, binds all-trans-retinyl esters, making them available for IMH (isomerohydrolase) processing to all-cis-retinol. The soluble form is regenerated by transferring its palmitoyl groups onto 11-cis-retinol, a reaction catalyzed by LRAT (PubMed:15186777).
Gene Name:
RPE65
Uniprot ID:
Q28175
Molecular weight:
60944.0
Reactions
cis-b,b-Carotene + Oxygen → Retinaldetails
General function:
Involved in extracellular ligand-gated ion channel acti
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. Rho-2 GABA receptor could play a role in retinal neurotransmission (By similarity).
Gene Name:
GABRR2
Uniprot ID:
Q0II76
Molecular weight:
54122.0
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 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:
Involved in retinal binding
Specific function:
Intracellular transport of retinol.
Gene Name:
RBP5
Uniprot ID:
P82708
Molecular weight:
15962.0
General function:
Involved in retinal binding
Specific function:
Cytoplasmic retinol-binding protein (PubMed:7744071). Accepts retinol from the transport protein STRA6, and thereby contributes to retinol uptake, storage and retinoid homeostasis.
Gene Name:
RBP1
Uniprot ID:
P02694
Molecular weight:
15823.0
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
IRBP shuttles 11-cis and all trans retinoids between the retinol isomerase in the pigment epithelium and the visual pigments in the photoreceptor cells of the retina.
Gene Name:
RBP3
Uniprot ID:
P12661
Molecular weight:
139698.0
General function:
Involved in retinal binding
Specific function:
Retinol-binding protein that mediates retinol transport in blood plasma. Delivers retinol from the liver stores to the peripheral tissues. Transfers the bound all-trans retinol to STRA6, that then facilitates retinol transport across the cell membrane.
Gene Name:
RBP4
Uniprot ID:
P18902
Molecular weight:
21069.0
General function:
Involved in G-protein coupled receptor activity
Specific function:
Receptor for all-trans- and 11-cis-retinal. Binds preferentially to the former and may catalyze the isomerization of the chromophore by a retinochrome-like mechanism.
Gene Name:
RGR
Uniprot ID:
P47803
Molecular weight:
31961.0