| Common Name |
11-cis-Retinaldehyde
| Description |
Vitamin A (all-trans retinol) is converted in the retina to the 11-cis-isomer of retinaldehyde or 11-cis-retinal. 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 implise 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 reslits from a failure to resynthesize 11-cis retinal rapidly (http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/vit_0260.shtml).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(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
RetinaldehydeMeSH
RetineneMeSH
RetinalMeSH
Aldehyde, vitamin aMeSH
Vitamin a aldehydeMeSH
AxerophthalMeSH
| Chemical Formlia |
C20H28O
| Average Molecliar Weight |
284.4357
| Monoisotopic Molecliar Weight |
284.214015518
| 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 Name |
11-cis-retinal
| CAS Registry Number |
564-87-4
| SMILES |
C/C(/C=CC=C(/C)C=CC1=C(C)CCCC1(C)C)=CC=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 Key |
NCYCYZXNIZJOKI-IOUUIBBYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities 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.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Lipids and lipid-like moleclies
| Sub Class |
Prenol lipids
| Direct Parent |
Retinoids
| Alternative Parents |
Diterpenoids
Enals
Organic oxides
Hydrocarbon derivatives
Aldehydes
| Substituents |
Retinoid skeleton
Diterpenoid
Enal
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homomonocyclic compound
| Molecliar Framework |
Aliphatic homomonocyclic compounds
| External Descriptors |
retinal (CHEBI:16066 )
Retinoids (C02110 )
Retinoids (LMPR01090003 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
Cell signaling
Fuel and energy storage
Fuel or energy source
Membrane integrity/stability
| Application |
Nutrients
Stabilizers
Surfactants and Emlisifiers
| Cellliar locations |
Cytoplasm
Extracellliar
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point63.5 – 64.4 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
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
Polarizability34.94 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
Membrane
| Biofluid Locations |
Not Available
| Tissue Location |
Testes
| Pathways |
| Name |
SMPDB Link |
KEGG Link |
Retinol MetabolismSMP00074map00830
Vitamin A DeficiencySMP00336Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022871
| KNApSAcK ID |
Not Available
| Chemspider ID |
4444130
| KEGG Compound ID |
C02110
| BioCyc ID |
CPD-881
| BiGG ID |
2265510
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB02152
| Metagene Link |
HMDB02152
| METLIN ID |
6513
| PubChem Compound |
5280490
| PDB ID |
Not Available
| ChEBI ID |
16066
Product: 9-Aminoacridine
References |
| Synthesis Reference |
Ito, 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 |
- 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 ]
- 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 ]
|
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
PMID: 18335063