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Record Information
Version3.6
Creation Date2006-08-13 01:02:39 UTC
Update Date2016-02-11 01:06:24 UTC
HMDB IDHMDB03598
Secondary Accession NumbersNone
Metabolite Identification
Common NameRetinyl ester
DescriptionRetinyl ester is a substrate for Lecithin retinol acyltransferase and Retinal pigment epithelium-specific 65 kDa protein.
Structure
Thumb
Synonyms
ValueSource
56-Dihydroretinoic acidChEMBL
all-e-Retinoic acidChEMBL
56-DihydroretinoateGenerator
all-e-RetinoateGenerator
all-trans-Retinyl esterHMDB
Chemical FormulaC20H30O2
Average Molecular Weight302.451
Monoisotopic Molecular Weight302.224580204
IUPAC Name(2E,4E,6E,8E)-3,7-dimethyl-9-(2,2,6-trimethylcyclohexyl)nona-2,4,6,8-tetraenoic acid
Traditional Nameretinyl ester
CAS Registry NumberNot Available
SMILES
CC1CCCC(C)(C)C1\C=C\C(\C)=C\C=C\C(\C)=C\C(O)=O
InChI Identifier
InChI=1S/C20H30O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14,17-18H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+
InChI KeyInChIKey=WWDMJSSVVPXVSV-YCNIQYBTSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Carbocyclic fatty acid
  • Medium-chain fatty acid
  • Methyl-branched fatty acid
  • Branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000878 mg/mLALOGPS
logP6.35ALOGPS
logP5.46ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.94ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.21 m3·mol-1ChemAxon
Polarizability37.07 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Adipose Tissue
  • Kidney
  • Liver
  • Stratum Corneum
Pathways
NameSMPDB LinkKEGG Link
Retinol MetabolismSMP00074map00830
Vitamin A DeficiencySMP00336Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.055 +/- 0.04 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.15 (0.03 - 0.046) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.054 +/- 0.035 uMAdult (>18 years old)FemaleOsteoporosis details
BloodDetected and Quantified0.2 (0.03 - 0.5) uMAdult (>18 years old)BothIdiopathic intracranial hypertension details
Associated Disorders and Diseases
Disease References
Idiopathic intracranial hypertension
  1. Jacobson DM, Berg R, Wall M, Digre KB, Corbett JJ, Ellefson RD: Serum vitamin A concentration is elevated in idiopathic intracranial hypertension. Neurology. 1999 Sep 22;53(5):1114-8. [10496276 ]
Osteoporosis
  1. Penniston KL, Weng N, Binkley N, Tanumihardjo SA: Serum retinyl esters are not elevated in postmenopausal women with and without osteoporosis whose preformed vitamin A intakes are high. Am J Clin Nutr. 2006 Dec;84(6):1350-6. [17158416 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023204
KNApSAcK IDNot Available
Chemspider ID10607936
KEGG Compound IDC02075
BioCyc IDCPD-437
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03598
Metagene LinkHMDB03598
METLIN ID6966
PubChem Compound5460164
PDB IDNot Available
ChEBI ID545914
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mills JP, Penniston KL, Tanumihardjo SA: Extra-hepatic vitamin A concentrations in captive Rhesus (Macaca mulatta) and Marmoset (Callithrix jacchus) monkeys fed excess vitamin A. Int J Vitam Nutr Res. 2005 Mar;75(2):126-32. [15929633 ]
  2. Zilversmit DB, Morton RE, Hughes LB, Thompson KH: Exchange of retinyl and cholesteryl esters between lipoproteins of rabbit plasma. Biochim Biophys Acta. 1982 Jul 20;712(1):88-93. [7115749 ]
  3. Kang S, Duell EA, Fisher GJ, Datta SC, Wang ZQ, Reddy AP, Tavakkol A, Yi JY, Griffiths CE, Elder JT, et al.: Application of retinol to human skin in vivo induces epidermal hyperplasia and cellular retinoid binding proteins characteristic of retinoic acid but without measurable retinoic acid levels or irritation. J Invest Dermatol. 1995 Oct;105(4):549-56. [7561157 ]
  4. Ribaya-Mercado JD, Blanco MC, Fox JG, Russell RM: High concentrations of vitamin A esters circulate primarily as retinyl stearate and are stored primarily as retinyl palmitate in ferret tissues. J Am Coll Nutr. 1994 Feb;13(1):83-6. [8157860 ]
  5. Stauber PM, Sherry B, VanderJagt DJ, Bhagavan HN, Garry PJ: A longitudinal study of the relationship between vitamin A supplementation and plasma retinol, retinyl esters, and liver enzyme activities in a healthy elderly population. Am J Clin Nutr. 1991 Nov;54(5):878-83. [1951160 ]
  6. Got L, Gousson T, Delacoux E: Simultaneous determination of retinyl esters and retinol in human livers by reversed-phase high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1995 Jun 23;668(2):233-9. [7581858 ]

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
Acyl-CoA + Vitamin A → Coenzyme A + Retinyl esterdetails
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:
RPE65
Uniprot ID:
Q16518
Molecular weight:
60947.08
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
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
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 (By similarity). Functions also as an acyl-CoA retinol acyltransferase (ARAT).
Gene Name:
DGAT2
Uniprot ID:
Q96PD7
Molecular weight:
39043.88
Reactions
Acyl-CoA + Vitamin A → Coenzyme A + Retinyl esterdetails
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:
AWAT1
Uniprot ID:
Q58HT5
Molecular weight:
37758.815
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:
AWAT2
Uniprot ID:
Q6E213
Molecular weight:
38093.25
Reactions
Acyl-CoA + Vitamin A → Coenzyme A + Retinyl esterdetails