Showing metabocard for Retinyl palmitate (BMDB0003648)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:05:43 UTC
Update Date2020-05-21 16:29:06 UTC
BMDB IDBMDB0003648
Secondary Accession Numbers
  • BMDB03648
Metabolite Identification
Common NameRetinyl palmitate
DescriptionRetinyl palmitate, also known as retinyl palmitate or retinyl palmitate, belongs to the class of organic compounds known as wax monoesters. These are waxes bearing an ester group at exactly one position. Retinyl palmitate is a drug. Retinyl palmitate exists as a solid very hydrophobic, practically insoluble (in water), and relatively neutral. In cattle, retinyl palmitate is involved in the metabolic pathway called the retinol metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenyl hexadecanoateChEBI
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8,tetraenyl hexadecanoic acid esterChEBI
AfaxinChEBI
all-trans-Retinol palmitateChEBI
all-trans-Retinyl hexadecanoateChEBI
AlphalinChEBI
Aquasol aChEBI
ArovitChEBI
Chocola aChEBI
O(15)-HexadecanoylretinolChEBI
Optovit-aChEBI
Retinol hexadecanoateChEBI
Retinol palmitateChEBI
Retinyl hexadecanoateChEBI
trans-Retinol palmitateChEBI
trans-Retinyl palmitateChEBI
Vitamin a palmitateChEBI
all-trans-Retinyl palmitateKegg
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenyl hexadecanoic acidGenerator
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8,tetraenyl hexadecanoate esterGenerator
all-trans-Retinol palmitic acidGenerator
all-trans-Retinyl hexadecanoic acidGenerator
Retinol hexadecanoic acidGenerator
Retinol palmitic acidGenerator
Retinyl hexadecanoic acidGenerator
trans-Retinol palmitic acidGenerator
trans-Retinyl palmitic acidGenerator
Vitamin a palmitic acidGenerator
all-trans-Retinyl palmitic acidGenerator
Retinyl palmitic acidGenerator
all-trans-Vitamin a palmitateHMDB
AquapalmHMDB
Axerophthol palmitateHMDB
Dispatabs tabsHMDB
Ester found in fish liver oilsHMDB
Lutavit a 500 plusHMDB
MyvakHMDB
MyvaxHMDB
Optovit aHMDB
Testavol SHMDB
Vitazyme aHMDB
Chemical FormulaC36H60O2
Average Molecular Weight524.8604
Monoisotopic Molecular Weight524.459331164
IUPAC Name(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl hexadecanoate
Traditional Namevitamin a palmitate
CAS Registry Number79-81-2
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-FFHKNEKCSA-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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point28.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability70.5 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, Positivesplash10-07vr-6590330000-c4a001ec8772bbd8b673View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00n0-0391040000-4bcb419b1aa363c5a184View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-3890000000-13b63fb441c04d797a5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053i-4910200000-ec9d8c6e06e67e406eaeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-0090050000-063ec803b899247ff625View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0090000000-ceacddaa1af7bfe01b93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052u-2090000000-010cffd7fdb5e0c0ae62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-0970350000-ae98e4da36c7fef49b01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-1960010000-e463420790c3679b3761View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01b9-3930000000-2209374e0a45d158da93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0060090000-71bf924b1d2a2be5b8a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0090010000-5bffb18764c70498c127View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9870000000-8e1a1ac617c6db688b0bView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Adipose Tissue
  • Epidermis
  • Fibroblasts
  • Intestine
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003648
DrugBank IDDBSALT000855
Phenol Explorer Compound IDNot Available
FooDB IDFDB030671
KNApSAcK IDNot Available
Chemspider ID4444162
KEGG Compound IDC02588
BioCyc IDCHOCOLA_A
BiGG IDNot Available
Wikipedia LinkRetinyl_palmitate
METLIN IDNot Available
PubChem Compound5280531
PDB IDNot Available
ChEBI ID17616
References
Synthesis ReferenceAjima, Ayako; Takahashi, Katsunobu; Matsushima, Ayako; Saito, Yuji; Inada, Yuji. Retinyl esters synthesis by polyethylene glycol-modified lipase in benzene. Biotechnology Letters (1986), 8(8), 547-52.
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