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Record Information
StatusExpected but not Quantified
Creation Date2007-05-22 17:49:55 UTC
Update Date2020-02-26 21:26:15 UTC
Secondary Accession Numbers
  • HMDB0003439
  • HMDB03439
  • HMDB06216
Metabolite Identification
Common Name11-cis-Retinol
DescriptionCis-11-retinol is produce from vitamin A cycle driven by interphotoreceptor retinoid binding protein(IRBP). cis-11-retinol is released from retinal pigment epithelium(RPE) membranes. (PMID: 10655150 ). Retinoid metabolism of RPE cells freshly isolated by trypsinization showed no 11- cis -retinal and little 11- cis -retinol formation. Nondamaged cells cultured on thermally responsive surfaces detached in sheets upon temperature change. They showed metabolism similar to that of cells freshly isolated by nonenzymatic means. After trypsinization, confluent cultures dissociated into individual cells, but these cells showed poor retinoid metabolism, including no detectable retinyl esters or 11- cis -retinoid isomers. (PMID: 10375454 ).
11-cis-Vitamin a alcoholHMDB
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
Aquasol aHMDB
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
InChI Identifier
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
  • 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

Route of exposure:


Biological location:


Naturally occurring process:


Industrial application:

Biological role:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.0076 g/LALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon


Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1190000000-346a3e44c44d46353e802017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-7139000000-7242603c3f7f12c824cd2017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-052r-2950000000-c24ec8ff8d0ba6c1f23f2018-05-25View Spectrum


Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0290000000-25c523b646154b291da82018-05-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05gj-3900000000-a63c286f931608f650a32018-05-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05mo-9700000000-e627db30469c74bb037f2018-05-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-1490000000-7205fba02aeb80622df82017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00m0-3920000000-951836eaf171751b137c2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lei-9810000000-b9b76a3e956e61a7d39e2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-575d71f5f53354f828c22017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0090000000-c71c47589510cf7c1a0b2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-3690000000-26f7587a1f34c10cd8f72017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-fe93459d3069e264b77f2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05mx-0190000000-f81760535f6050971f922021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00li-0960000000-4dbc516b202b90a6c2652021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-015i-1890000000-fb68e645ac6c84dc722c2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05a9-2910000000-aa07b89a9cfe132b87252021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06dl-5900000000-6de72efc591b252620c92021-09-08View Spectrum


Spectrum TypeDescriptionDeposition DateView
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, predicted)2018-05-25View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
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 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
Food Biomarker OntologyNot Available
MarkerDB IDNot Available
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 References
  1. Edwards RB, Adler AJ: IRBP enhances removal of 11- cis -retinaldehyde from isolated RPE membranes. Exp Eye Res. 2000 Feb;70(2):235-45. [PubMed:10655150 ]
  2. von Recum HA, Okano T, Kim SW, Bernstein PS: Maintenance of retinoid metabolism in human retinal pigment epithelium cell culture. Exp Eye Res. 1999 Jul;69(1):97-107. [PubMed:10375454 ]


General function:
Involved in diacylglycerol O-acyltransferase activity
Specific function:
Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. In contrast to DGAT2 it is not essential for survival. May be involved in VLDL (very low density lipoprotein) assembly. In liver, plays a role in esterifying exogenous fatty acids to glycerol. Functions as the major acyl-CoA retinol acyltransferase (ARAT) in the skin, where it acts to maintain retinoid homeostasis and prevent retinoid toxicity leading to skin and hair disorders.
Gene Name:
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Molecular weight:
Palmityl-CoA + 11-cis-Retinol → Coenzyme A + 11-cis-Retinyl palmitatedetails
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:
Uniprot ID:
Molecular weight:
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Plays important roles in the production of 11-cis retinal and in visual pigment regeneration. 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. The enzymatic activity is linearly dependent of the expression levels and membrane association.
Gene Name:
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Molecular weight:
An all-trans-retinyl ester + Water → 11-cis-Retinol + a fatty aciddetails
Retinyl ester + Water → 11-cis-Retinol + Fatty aciddetails
General function:
Involved in phosphatidylcholine-retinol O-acyltransfera
Specific function:
Transfers the acyl group from the sn-1 position of phosphatidylcholine to all-trans retinol, producing all-trans retinyl esters. Retinyl esters are storage forms of vitamin A. LRAT plays a critical role in vision. It provides the all-trans retinyl ester substrates for the isomerohydrolase which processes the esters into 11-cis-retinol in the retinal pigment epithelium; due to a membrane-associated alcohol dehydrogenase, 11 cis-retinol is oxidized and converted into 11-cis-retinaldehyde which is the chromophore for rhodopsin and the cone photopigments.
Gene Name:
Uniprot ID:
Molecular weight:
Palmitoylphosphatidylcholine + 11-cis-Retinol → 11-cis-Retinyl palmitate + 2-Acyl-sn-glycero-3-phosphocholinedetails
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Acyltransferase that predominantly esterify long chain (wax) alcohols with acyl-CoA-derived fatty acids to produce wax esters. Wax esters are enriched in sebum, suggesting that it plays a central role in lipid metabolism in skin. Has a preference for arachidyl alcohol as well as decyl alcohol, demonstrating its relatively poor activity using saturated long chain alcohols (C16, C18, and C20).
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Acyltransferase that predominantly esterify long chain (wax) alcohols with acyl-CoA-derived fatty acids to produce wax esters. Wax esters are enriched in sebum, suggesting that it plays a central role in lipid metabolism in skin. Has no activity using decyl alcohol and significantly prefers the C16 and C18 alcohols. May also have 2-acylglycerol O-acyltransferase (MGAT) and acyl-CoA:retinol acyltransferase (ARAT) activities, to catalyze the synthesis of diacylglycerols and retinyl esters; however this activity is unclear in vivo.
Gene Name:
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Molecular weight: