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Record Information
Version1.0
Created at2006-05-22 14:17:38 UTC
Updated at2021-06-29 00:47:23 UTC
NP-MRD IDNP0001147
Secondary Accession NumbersNone
Natural Product 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
Thumb
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 RetinalHMDB
RetinaldehydeHMDB
RetineneHMDB
RetinalHMDB
Aldehyde, vitamin aHMDB
Vitamin a aldehydeHMDB
AxerophthalHMDB
Chemical FormulaC20H28O
Average Mass284.4357 Da
Monoisotopic Mass284.21402 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchos
Anatidae
Anser anser
Bison bison
Bos taurus
Bos taurus X Bison bison
Bubalus bubalis
Capra aegagrus hircus
Cervidae
Cervus canadensis
Columba
Columbidae
Dromaius novaehollandiae
Equus caballus
Gallus gallus
Homo sapiensLOTUS Database
Lagopus muta
Leporidae
Lepus timidus
Melanitta fusca
Meleagris gallopavo
Mus musculusLOTUS Database
Numida meleagris
Odocoileus
Oryctolagus
Ovis aries
Phasianidae
Phasianus colchicus
Struthio camelus
Sus scrofa
Sus scrofa domestica
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point63.5 - 64.4 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
HMDB IDHMDB0002152
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
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 ]
  4. Edwards RB, Adler AJ: IRBP enhances removal of 11- cis -retinaldehyde from isolated RPE membranes. Exp Eye Res. 2000 Feb;70(2):235-45. doi: 10.1006/exer.1999.0781. [PubMed:10655150 ]
  5. Shaw NS, Noy N: Interphotoreceptor retinoid-binding protein contains three retinoid binding sites. Exp Eye Res. 2001 Feb;72(2):183-90. doi: 10.1006/exer.2000.0945. [PubMed:11161734 ]