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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:29 UTC
Update Date2020-02-26 21:25:45 UTC
HMDB IDHMDB0005181
Secondary Accession Numbers
  • HMDB05181
Metabolite Identification
Common NameDolichol-14
DescriptionDolichols are polyisoprenic molecule ubiquitously present in the lipid fraction of animal and plant tissues, discovered 40 years ago during experiments on the biosynthesis of ubiquinone. The molecular structure of dolichol comprises a sequence of unsaturated isoprenic units bearing a primary terminal hydroxyl group. The length of dolichyl chains depends on the species of the organism from which they are isolated. Mammalian dolichol generally is made up of 16 to 23 unsaturated isoprene units, and the terminal hydroxyl group may exist either free or esterified with fatty acids, phosphoric acid, and pyrophosphoric acid. In biological membranes, this linear polyisoprenoid compound may be located between the two leaflets of the lipid bilayer, close to the free end of the phospholipid fatty acid molecules. Metabolism and function of dolichol were largely unknown until recently. Synthesis of dolichol by the mevalonate pathway was demonstrated in vitro and in vivo in many tissues. The isoprenoid pyrophosphate intermediates are shared by the cholesterol, dolichol, and ubiquinone pathways, and treatment with drugs that block hydroxymethyl glutaryl coenzyme A reductase may significantly decrease their plasma and tissue levels. In humans, there is no apparent positive correlation between serum dolichol and tissue dolichol and age. In view of the total content of the body, half-life of the total body dolichol, and dolichol content in the extracellular space, it was concluded that the dolichol in tissues probably derives from biosynthesis in those tissues and that relocation of dolichol via circulation cannot be prominent in vivo. The levels of dolichol in human serum have apparently no correlation to age or serum total cholesterol, and exhibit a linear correlation to high-density lipoprotein cholesterols which may reflect the fact that the dolichols are associated with the high-density lipoprotein fraction. No enzymic pathways for dolichol degradation were described, but no case of dolichol-storage disease was reported. Shrinkage of tissue because of increased lysosomal degradation in the process of atrophy does not affect the dolichol content and concentration increases. Small quantities of dolichol that may be excreted into the urine at least in part is derived from the lysosomes of the excretory organ, and serum dolichol levels may be elevated in chronic cholestatic liver diseases. Recent evidence shows that phagocytosis may cause the degradation and disposal of the engulfed dolichol, possibly because of nonenzymatic free radical mediated decomposition. By means of a 1H-nuclear magnetic resonance (NMR) analytical method, the hypothesis was substantiated that dolichol may act as a free-radical scavenger in the cell membranes and protect polyunsaturated fatty acids from peroxidation, and that it may undergo decomposition in the process. (PMID 15741281 ).
Structure
Data?1582752345
Synonyms
ValueSource
alpha-DihydrotetradecaprenolHMDB
Chemical FormulaC70H114O
Average Molecular Weight971.6536
Monoisotopic Molecular Weight970.88696827
IUPAC Name(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E,42E,46E,50E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55-tetradecamethylhexapentaconta-2,6,10,14,18,22,26,30,34,38,42,46,50,54-tetradecaen-1-ol
Traditional Name(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E,42E,46E,50E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55-tetradecamethylhexapentaconta-2,6,10,14,18,22,26,30,34,38,42,46,50,54-tetradecaen-1-ol
CAS Registry Number118204-12-9
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CO
InChI Identifier
InChI=1S/C70H114O/c1-57(2)29-16-30-58(3)31-17-32-59(4)33-18-34-60(5)35-19-36-61(6)37-20-38-62(7)39-21-40-63(8)41-22-42-64(9)43-23-44-65(10)45-24-46-66(11)47-25-48-67(12)49-26-50-68(13)51-27-52-69(14)53-28-54-70(15)55-56-71/h29,31,33,35,37,39,41,43,45,47,49,51,53,55,71H,16-28,30,32,34,36,38,40,42,44,46,48,50,52,54,56H2,1-15H3/b58-31+,59-33+,60-35+,61-37+,62-39+,63-41+,64-43+,65-45+,66-47+,67-49+,68-51+,69-53+,70-55+
InChI KeyDLNRMPLOFNVUTQ-WIKVCOJLSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as polyprenols. These are prenols with more than 4 consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenols
Direct ParentPolyprenols
Alternative Parents
Substituents
  • Polyterpenoid
  • Bactoprenol
  • Polyprenol skeleton
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility0.00022 g/LALOGPS
logP9.77ALOGPS
logP22.42ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)16.33ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity336.81 m³·mol⁻¹ChemAxon
Polarizability134.32 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000009-edf5d7a54751edcd616aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0323313229-ba9ce09796a3fbe7dabbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-3872164229-99abfbe7ffd6369d6c51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000009-8f7fd88207ab895eb230Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0000000009-6b2aa23db5b793383f61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-1101010009-519da682fbb6cab36770Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • 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 IDFDB023634
KNApSAcK IDNot Available
Chemspider ID4947397
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6443375
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Parentini I, Cavallini G, Donati A, Gori Z, Bergamini E: Accumulation of dolichol in older tissues satisfies the proposed criteria to be qualified a biomarker of aging. J Gerontol A Biol Sci Med Sci. 2005 Jan;60(1):39-43. [PubMed:15741281 ]