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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:54:45 UTC
Update Date2019-07-23 07:14:06 UTC
HMDB IDHMDB0060338
Secondary Accession Numbers
  • HMDB0062280
  • HMDB60338
  • HMDB62280
Metabolite Identification
Common Name11-cis-Retinyl palmitate
Description11-cis-Retinyl palmitate, also known as 11-cis-retinyl hexadecanoate, belongs to the class of organic compounds known as wax monoesters. These are waxes bearing an ester group at exactly one position. 11-cis-Retinyl palmitate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866046
Synonyms
ValueSource
11-cis-Retinyl hexadecanoateChEBI
11-cis-Retinyl hexadecanoic acidGenerator
11-cis-Retinyl palmitic acidGenerator
Chemical FormulaC36H60O2
Average Molecular Weight524.8604
Monoisotopic Molecular Weight524.459331164
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-yl hexadecanoate
Traditional Name11-cis-retinyl palmitate
CAS Registry Number51249-33-3
SMILES
CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C
InChI Identifier
InChI=1S/C36H60O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-25-35(37)38-30-28-32(3)23-20-22-31(2)26-27-34-33(4)24-21-29-36(34,5)6/h20,22-23,26-28H,7-19,21,24-25,29-30H2,1-6H3/b23-20-,27-26+,31-22+,32-28+
InChI KeyVYGQUTWHTHXGQB-SXFSSFKVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as wax monoesters. These are waxes bearing an ester group at exactly one position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentWax monoesters
Alternative Parents
Substituents
  • Wax monoester skeleton
  • Retinoid skeleton
  • Diterpenoid
  • Fatty alcohol ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility8.1e-05 g/LALOGPS
logP10.12ALOGPS
logP11.62ChemAxon
logS-6.8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity171.51 m³·mol⁻¹ChemAxon
Polarizability69.43 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+236.80531661259
DarkChem[M-H]-238.37631661259
DeepCCS[M+H]+246.53630932474
DeepCCS[M-H]-244.1430932474
DeepCCS[M-2H]-277.02330932474
DeepCCS[M+Na]+253.01430932474
AllCCS[M+H]+240.932859911
AllCCS[M+H-H2O]+239.932859911
AllCCS[M+NH4]+241.932859911
AllCCS[M+Na]+242.232859911
AllCCS[M-H]-215.632859911
AllCCS[M+Na-2H]-220.432859911
AllCCS[M+HCOO]-225.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
11-cis-Retinyl palmitateCCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C4434.3Standard polar33892256
11-cis-Retinyl palmitateCCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C3730.3Standard non polar33892256
11-cis-Retinyl palmitateCCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C3967.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 11-cis-Retinyl palmitate GC-MS (Non-derivatized) - 70eV, Positivesplash10-07vr-6590330000-c4a001ec8772bbd8b6732017-09-20Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinyl palmitate 10V, Positive-QTOFsplash10-00p0-0491040000-c8a67fd69e259a36e93f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinyl palmitate 20V, Positive-QTOFsplash10-00li-3960000000-70ca5c3efbf40f8f5ea02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinyl palmitate 40V, Positive-QTOFsplash10-001r-4910200000-144f35be46c93e2dabae2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinyl palmitate 10V, Negative-QTOFsplash10-00dr-0090060000-d5d329dcb92a786695242017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinyl palmitate 20V, Negative-QTOFsplash10-0a4r-0090000000-70a2377fe27466902ed92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinyl palmitate 40V, Negative-QTOFsplash10-0a4u-2090000000-1ce0ef84e65a72b91a2c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinyl palmitate 10V, Positive-QTOFsplash10-00or-0970350000-ae98e4da36c7fef49b012021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinyl palmitate 20V, Positive-QTOFsplash10-00kr-1960010000-e463420790c3679b37612021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinyl palmitate 40V, Positive-QTOFsplash10-01b9-3930000000-2209374e0a45d158da932021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinyl palmitate 10V, Negative-QTOFsplash10-00di-0060090000-71bf924b1d2a2be5b8a82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinyl palmitate 20V, Negative-QTOFsplash10-0a4i-0090010000-91666b90277e61ac39692021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-cis-Retinyl palmitate 40V, Negative-QTOFsplash10-0a4l-9870000000-8e1a1ac617c6db688b0b2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID4573590
KEGG Compound IDC03455
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5459829
PDB IDNot Available
ChEBI ID16254
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

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:
DGAT1
Uniprot ID:
O75907
Molecular weight:
55277.735
Reactions
Palmityl-CoA + 11-cis-Retinol → Coenzyme A + 11-cis-Retinyl palmitatedetails
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:
LRAT
Uniprot ID:
O95237
Molecular weight:
25702.635
Reactions
Palmitoylphosphatidylcholine + 11-cis-Retinol → 11-cis-Retinyl palmitate + 2-Acyl-sn-glycero-3-phosphocholinedetails