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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:38 UTC
Update Date2022-03-07 02:49:13 UTC
HMDB IDHMDB0002152
Secondary Accession Numbers
  • HMDB02152
Metabolite Identification
Common Name11-cis-Retinaldehyde
Description11-cis-retinal is a retinal having 2E,4Z,6E,8E-double bond geometry. It has a role as a chromophore, a human metabolite and a mouse metabolite. It is a diterpene derived from the carotenoid vitamin A which functions as the active component of the visual cycle. It is the prosthetic group of rhodopsin. When stimulated by visible light, rhodopsin transforms this cis-isomer of retinal to the trans-isomer (11-trans-retinal). This transformation straightens-out the bend of the retinal molecule and causes a change in the shape of rhodopsin triggering the visual process. A series of energy-requiring enzyme-catalyzed reactions convert the 11-trans-retinal back to the cis-isomer. 11-cis-retinal functions in the retina in the transduction of light into the neural signals necessary for vision. 11-cis-retinal, while attached to opsin in rhodopsin is isomerized to all-trans-retinal by light. This is the event that triggers the nerve impulse to the brain which allows for the perception of light. All-trans-retinal is then released from opsin and reduced to all-trans-retinol. All-trans-retinol is isomerized to 11-cis-retinol in the dark, and then oxidized to 11-cis-retinal. 11-cis-retinal recombines with opsin to re-form rhodopsin. Night blindness or defective vision at low illumination results from a failure to resynthesize 11-cis retinal rapidly.
Structure
Data?1582752232
Synonyms
ValueSource
(2E,4Z,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenalChEBI
11-cis-RetineneChEBI
11-cis-Vitamin a aldehydeChEBI
11-cis-RetinalHMDB
cis-11-RetinalHMDB
11 cis RetinalMeSH, HMDB
RetinaldehydeMeSH, HMDB
RetineneMeSH, HMDB
RetinalMeSH, HMDB
Aldehyde, vitamin aMeSH, HMDB
Vitamin a aldehydeMeSH, HMDB
AxerophthalMeSH, HMDB
Chemical FormulaC20H28O
Average Molecular Weight284.4357
Monoisotopic Molecular Weight284.214015518
IUPAC Name(2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal
Traditional Name11-cis-retinal
CAS Registry Number564-87-4
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-IOUUIBBYSA-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
Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point63.5 - 64.4 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0042 g/LALOGPS
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
Polarizability34.82 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+173.52431661259
DarkChem[M-H]-173.4831661259
DeepCCS[M+H]+180.13330932474
DeepCCS[M-H]-177.77530932474
DeepCCS[M-2H]-211.43730932474
DeepCCS[M+Na]+186.66330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
11-cis-RetinaldehydeC/C(/C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C\C=O3063.2Standard polar33892256
11-cis-RetinaldehydeC/C(/C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C\C=O2469.4Standard non polar33892256
11-cis-RetinaldehydeC/C(/C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C\C=O2398.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 11-cis-Retinaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-2290000000-df9d2aa7545cc60a54f92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11-cis-Retinaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11-cis-Retinaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinaldehyde 10V, Positive-QTOFsplash10-000i-1490000000-97cddfba9819c34173862017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinaldehyde 20V, Positive-QTOFsplash10-001s-3920000000-0be8a19c3cba33e3b06b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinaldehyde 40V, Positive-QTOFsplash10-0kui-9720000000-a579102a9f5600032e3f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinaldehyde 10V, Negative-QTOFsplash10-001i-0090000000-e7d5d678e91ec531c2ae2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinaldehyde 20V, Negative-QTOFsplash10-0a59-0090000000-8af2668c966a1c8a3cef2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinaldehyde 40V, Negative-QTOFsplash10-00ku-3690000000-54506b9021b67caed0412017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinaldehyde 10V, Positive-QTOFsplash10-00n3-1960000000-43f8c66f164764c373612021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinaldehyde 20V, Positive-QTOFsplash10-0609-3920000000-dbeab0a82b306761cf6a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinaldehyde 40V, Positive-QTOFsplash10-052f-7900000000-d2bb7c1aeeb87d8833d22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinaldehyde 10V, Negative-QTOFsplash10-0a59-0090000000-2ec2f8f314943441fa152021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinaldehyde 20V, Negative-QTOFsplash10-0pb9-0190000000-312cebb17ccd0189ab4d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinaldehyde 40V, Negative-QTOFsplash10-000i-1590000000-b2551eac481c0c930a4d2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2018-05-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue Locations
  • Testis
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022871
KNApSAcK IDNot Available
Chemspider ID4444130
KEGG Compound IDC02110
BioCyc IDCPD-881
BiGG ID2265510
Wikipedia LinkNot Available
METLIN ID6513
PubChem Compound5280490
PDB IDNot Available
ChEBI ID16066
Food Biomarker OntologyNot Available
VMH IDRETINAL_11_CIS
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceIto, Masayoshi; Wada, Akimori. Preparation of 11-cis-Retinal and their intermediates. Jpn. Kokai Tokkyo Koho (1998), 12 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Bankson DD, Russell RM, Sadowski JA: Determination of retinyl esters and retinol in serum or plasma by normal-phase liquid chromatography: method and applications. Clin Chem. 1986 Jan;32(1 Pt 1):35-40. [PubMed:3940733 ]
  2. Futterman S, Saari JC: Occurrence of 11-cis-retinal-binding protein restricted to the retina. Invest Ophthalmol Vis Sci. 1977 Aug;16(8):768-71. [PubMed:560359 ]
  3. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]

Enzymes

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