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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:24 UTC
HMDB IDHMDB01358
Secondary Accession NumbersNone
Metabolite Identification
Common NameRetinal
DescriptionRetinal is a carotenoid constituent of visual pigments. It is the oxidized form of retinol which functions as the active component of the visual cycle. It is bound to the protein opsin forming the complex rhodopsin. When stimulated by visible light, the retinal component of the rhodopsin complex undergoes isomerization at the 11-position of the double bond to the cis-form; this is reversed in "dark" reactions to return to the native trans-configuration.
Structure
Thumb
Synonyms
ValueSource
all-trans-RetinaldehydeChEBI
all-trans-RetineneChEBI
all-trans-Vitamin a aldehydeChEBI
RetinalChEBI
RetinaldehydeChEBI
RetineneChEBI
Vitamin a aldehydeChEBI
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
AxerophthalHMDB
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 KeyInChIKey=NCYCYZXNIZJOKI-OVSJKPMPSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of Retinol metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point63 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0042 mg/mLALOGPS
logP6.62ALOGPS
logP4.86ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity96.87 m3·mol-1ChemAxon
Polarizability35.7 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Adrenal Cortex
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Lung
  • Muscle
  • Myelin
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Spleen
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Retinol MetabolismSMP00074map00830
Vitamin A DeficiencySMP00336Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.155 +/- 0.232 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022576
KNApSAcK IDNot Available
Chemspider ID553582
KEGG Compound IDC00376
BioCyc IDCPD-881
BiGG ID34795
Wikipedia LinkRetinal
NuGOwiki LinkHMDB01358
Metagene LinkHMDB01358
METLIN ID6188
PubChem Compound638015
PDB IDRET
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)Download (PDF)
General References
  1. Chang M, Herbert WN: Retinal arteriolar occlusions following amniotic fluid embolism. Ophthalmology. 1984 Dec;91(12):1634-7. [6521996 ]
  2. Nguyen QD, Van Do D, Feke GT, Demirjian ZN, Lashkari K: Heparin-induced antiheparin-platelet antibody associated with retinal venous thrombosis. Ophthalmology. 2003 Mar;110(3):600-3. [12623829 ]
  3. Aarli JA, Mork SJ, Myrseth E, Larsen JL: Glioblastoma associated with multiple sclerosis: coincidence or induction? Eur Neurol. 1989;29(6):312-6. [2691257 ]
  4. Wu WC, Lai CC, Liu JH, Singh T, Li LM, Peumans WJ, Van Damme EJ, Wu AM: Differential Binding to Glycotopes Among the Layers of Three Mammalian Retinal Neurons by Man-Containing N-linked Glycan, T(alpha) (Galbeta1-3GalNAcalpha1-), Tn (GalNAcalpha1-Ser/Thr) and I (beta)/II (beta) (Galbeta1-3/4GlcNAcbeta-) Reactive Lectins. Neurochem Res. 2006 May 23;. [16718528 ]
  5. Jankowska R, Witkowska D, Porebska I, Kuropatwa M, Kurowska E, Gorczyca WA: Serum antibodies to retinal antigens in lung cancer and sarcoidosis. Pathobiology. 2004;71(6):323-8. [15627843 ]
  6. Weiland JD, Liu W, Humayun MS: Retinal prosthesis. Annu Rev Biomed Eng. 2005;7:361-401. [16004575 ]
  7. Fukushima A, Ueno H, Fujimoto S: Antigenic cross-reactivity between human T lymphotropic virus type I (HTLV-I) and retinal antigens recognized by T cells. Clin Exp Immunol. 1994 Mar;95(3):459-64. [8137541 ]
  8. Bradbury MW, Lightman SL: The blood-brain interface. Eye. 1990;4 ( Pt 2):249-54. [2199234 ]
  9. Bringmann A, Reichenbach A, Wiedemann P: Pathomechanisms of cystoid macular edema. Ophthalmic Res. 2004 Sep-Oct;36(5):241-9. [15583429 ]
  10. Wu WC, Lai CC, Liu JH, Singh T, Li LM, Peumans WJ, Van Damme EJ, Wu AM: Differential binding to glycotopes among the layers of three mammalian retinal neurons by man-containing N-linked glycan, T(alpha) (Galbeta1-3GalNAcalpha1-), Tn (GalNAcalpha1-Ser/Thr) and I (beta)/II (beta) (Galbeta1-3/4GlcNAcbeta-) reactive lectins. Neurochem Res. 2006 May;31(5):619-28. Epub 2006 May 23. [16770733 ]
  11. Yamashiro K, Tsujikawa A, Ishida S, Usui T, Kaji Y, Honda Y, Ogura Y, Adamis AP: Platelets accumulate in the diabetic retinal vasculature following endothelial death and suppress blood-retinal barrier breakdown. Am J Pathol. 2003 Jul;163(1):253-9. [12819029 ]
  12. Ramirez JM, Ramirez AI, Salazar JJ, de Hoz R, Trivino A: Changes of astrocytes in retinal ageing and age-related macular degeneration. Exp Eye Res. 2001 Nov;73(5):601-15. [11747361 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Binds free retinal and cellular retinol-binding protein-bound retinal. Can convert/oxidize retinaldehyde to retinoic acid (By similarity).
Gene Name:
ALDH1A1
Uniprot ID:
P00352
Molecular weight:
54861.44
Reactions
Retinal + NAD + Water → 13-cis-Retinoic acid + NADHdetails
Retinal + NAD + Water → All-trans-retinoic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Does metabolize octanal and decanal but does not metabolize citral, benzaldehyde, acetaldehyde and propanal efficiently (By similarity).
Gene Name:
ALDH1A2
Uniprot ID:
O94788
Molecular weight:
54672.24
Reactions
Retinal + NAD + Water → 13-cis-Retinoic acid + NADHdetails
Retinal + NAD + Water → All-trans-retinoic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Stereospecific 11-cis retinol dehydrogenase, which catalyzes the final step in the biosynthesis of 11-cis retinaldehyde, the universal chromophore of visual pigments. Also able to oxidize 9-cis-retinol and 13-cis-retinol, but not all-trans-retinol. Active in the presence of NAD as cofactor but not in the presence of NADP.
Gene Name:
RDH5
Uniprot ID:
Q92781
Molecular weight:
34978.425
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH4
Uniprot ID:
P08319
Molecular weight:
40221.335
Reactions
Vitamin A + NAD → Retinal + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:
ADH5
Uniprot ID:
P11766
Molecular weight:
39723.945
Reactions
Vitamin A + NAD → Retinal + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1B
Uniprot ID:
P00325
Molecular weight:
39835.17
Reactions
Vitamin A + NAD → Retinal + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Could function in retinol oxidation for the synthesis of retinoic acid, a hormone important for cellular differentiation. Medium-chain (octanol) and aromatic (m-nitrobenzaldehyde) compounds are the best substrates. Ethanol is not a good substrate but at the high ethanol concentrations reached in the digestive tract, it plays a role in the ethanol oxidation and contributes to the first pass ethanol metabolism.
Gene Name:
ADH7
Uniprot ID:
P40394
Molecular weight:
41480.985
Reactions
Vitamin A + NAD → Retinal + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1A
Uniprot ID:
P07327
Molecular weight:
39858.37
Reactions
Vitamin A + NAD → Retinal + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH6
Uniprot ID:
P28332
Molecular weight:
39072.275
Reactions
Vitamin A + NAD → Retinal + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1C
Uniprot ID:
P00326
Molecular weight:
39867.27
Reactions
Vitamin A + NAD → Retinal + NADH + Hydrogen Iondetails
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Symmetrically cleaves beta-carotene into two molecules of retinal. The reaction proceeds in three stages, epoxidation of the 15,15'-double bond, hydration of the double bond leading to ring opening, and oxidative cleavage of the diol formed.
Gene Name:
BCMO1
Uniprot ID:
Q9HAY6
Molecular weight:
62636.69
Reactions
B-Carotene + Oxygen → Retinaldetails
15,15'-Dihydroxy-beta-carotene + Acceptor → Retinal + Reduced acceptordetails
General function:
Involved in oxidoreductase activity
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.
Gene Name:
HSD17B6
Uniprot ID:
O14756
Molecular weight:
35965.41
Reactions
Vitamin A + NAD → Retinal + NADH + Hydrogen Iondetails
General function:
Involved in estradiol 17-beta-dehydrogenase activity
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 (By similarity).
Gene Name:
RDH8
Uniprot ID:
Q9NYR8
Molecular weight:
35804.24
Reactions
Vitamin A + NADP → Retinal + NADPHdetails
General function:
Involved in oxidoreductase activity
Specific function:
Exhibits an oxidoreductive catalytic activity towards retinoids. Most efficient as an NADPH-dependent retinal reductase. Displays high activity towards 9-cis and all-trans-retinol. Also involved in the metabolism of short-chain aldehydes. No steroid dehydrogenase activity detected.
Gene Name:
RDH11
Uniprot ID:
Q8TC12
Molecular weight:
35385.955
Reactions
Vitamin A + NADP → Retinal + NADPHdetails
General function:
Involved in oxidoreductase activity
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.
Gene Name:
RDH10
Uniprot ID:
Q8IZV5
Molecular weight:
38087.16
Reactions
Vitamin A + NADP → Retinal + NADPHdetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the reduction of all-trans-retinal to all-trans-retinol in the presence of NADPH.
Gene Name:
DHRS3
Uniprot ID:
O75911
Molecular weight:
33548.115
Reactions
Vitamin A + NADP → Retinal + NADPHdetails
General function:
Involved in G-protein coupled receptor protein signaling pathway
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:
P47804
Molecular weight:
31873.8
General function:
Not Available
Specific function:
Oxidoreductase with strong preference for NAD. Active in both the oxidative and reductive directions. Oxidizes all-trans-retinol in all-trans-retinaldehyde. No activity was detected with 11-cis-retinol or 11-cis-retinaldehyde as substrates with either NAD(+)/NADH or NADP(+)/NADPH.
Gene Name:
SDR16C5
Uniprot ID:
Q8N3Y7
Molecular weight:
34095.0
Reactions
Vitamin A + NAD → Retinal + NADH + Hydrogen Iondetails