Showing metabocard for 11-cis-Retinol (BMDB0006216)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:20:25 UTC
Update Date2020-05-21 16:29:06 UTC
BMDB IDBMDB0006216
Secondary Accession Numbers
  • BMDB06216
Metabolite Identification
Common Name11-cis-Retinol
DescriptionVitamin a, also known as (13cis)-retinol, 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, vitamin a is considered to be an isoprenoid lipid molecule. Vitamin a is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Vitamin a exists in all living organisms, ranging from bacteria to humans. Vitamin a participates in a number of enzymatic reactions, within cattle. In particular, Vitamin a and acetyl-CoA can be converted into retinyl ester through the action of the enzyme diacylglycerol O-acyltransferase 1. In addition, Vitamin a and acetyl-CoA can be converted into retinyl ester through the action of the enzyme acyl-CoA wax alcohol acyltransferase 1. In cattle, vitamin a is involved in the metabolic pathway called the retinol metabolism pathway. Vitamin a is a potentially toxic compound. Vitamin a has been found to be associated with several diseases known as pregnancy, hemodialysis, and thyroid cancer; also vitamin a has been linked to the inborn metabolic disorders including abetalipoproteinemia.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
11-cis-Vitamin a alcoholHMDB
cis-11-RetinolHMDB
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol, (all-e)-isomerHMDB
all trans RetinolHMDB
all-trans-RetinolHMDB
Aquasol aHMDB
RetinolHMDB
Vitamin aHMDB
Vitamin a1HMDB
Chemical FormulaC20H30O
Average Molecular Weight286.4516
Monoisotopic Molecular Weight286.229665582
IUPAC Name(2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
Traditional Namevitamin a
CAS Registry Number22737-96-8
SMILES
C\C(=C/CO)\C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C
InChI Identifier
InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6-,12-11+,16-8+,17-13+
InChI KeyFPIPGXGPPPQFEQ-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
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • 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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.38ALOGPS
logP4.69ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)16.44ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.92 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, Positivesplash10-00di-1190000000-346a3e44c44d46353e80View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-7139000000-7242603c3f7f12c824cdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0290000000-25c523b646154b291da8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05gj-3900000000-a63c286f931608f650a3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05mo-9700000000-e627db30469c74bb037fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-1490000000-7205fba02aeb80622df8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00m0-3920000000-951836eaf171751b137cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lei-9810000000-b9b76a3e956e61a7d39eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-575d71f5f53354f828c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0090000000-c71c47589510cf7c1a0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-3690000000-26f7587a1f34c10cd8f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-fe93459d3069e264b77fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05mx-0190000000-f81760535f6050971f92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00li-0960000000-4dbc516b202b90a6c265View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-015i-1890000000-fb68e645ac6c84dc722cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05a9-2910000000-aa07b89a9cfe132b8725View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06dl-5900000000-6de72efc591b252620c9View in MoNA
MSMass Spectrum (Electron Ionization)splash10-052r-2950000000-c24ec8ff8d0ba6c1f23fView in MoNA
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006216
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023840
KNApSAcK IDNot Available
Chemspider ID4444073
KEGG Compound IDC00899
BioCyc IDCPD-882
BiGG ID2265508
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280382
PDB IDNot Available
ChEBI ID16302
References
Synthesis ReferenceBrown, Paul K.; Wald, George. The neo-b isomer of vitamin A and retinine. Journal of Biological Chemistry (1956), 222 865-77.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Diacylglycerol O-acyltransferase 2
General function:
Involved in diacylglycerol O-acyltransferase activity
Specific function:
Essential acyltransferase that catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. Required for synthesis and storage of intracellular triglycerides. Probably plays a central role in cytosolic lipid accumulation. In liver, is primarily responsible for incorporating endogenously synthesized fatty acids into triglycerides. Functions also as an acyl-CoA retinol acyltransferase (ARAT) (By similarity).
Gene Name:
DGAT2
Uniprot ID:
Q70VZ8
Molecular weight:
40896.0
Reactions
11-cis-Retinol + Acetyl-CoA → Retinyl palmitate + Coenzyme Adetails
Enzyme Details
2. Retinol dehydrogenase 12
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 + NADP → 11-cis-Retinol + NADPHdetails
Enzyme Details
3. Retinoid isomerohydrolase
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
Retinyl ester + Water → 11-cis-Retinol + Fatty Aciddetails