Record Information
Version1.0
Creation date2011-09-21 00:32:42 UTC
Update date2015-07-21 06:57:48 UTC
Primary IDFDB023633
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDolichol-20
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) [HMDB]
CAS Number2067-66-5
Structure
Thumb
Synonyms
SynonymSource
DolicholHMDB
Dolichol (C100)HMDB
Dolichol 20HMDB
Dolichol ateHMDB
Dolichyl ateHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.00022 g/LALOGPS
logP9.62ALOGPS
logP32.63ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)17.11ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count59ChemAxon
Refractivity478.93 m³·mol⁻¹ChemAxon
Polarizability189.77 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC100H164O
IUPAC name3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79-icosamethyloctaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78-nonadecaen-1-ol
InChI IdentifierInChI=1S/C100H164O/c1-81(2)41-22-42-82(3)43-23-44-83(4)45-24-46-84(5)47-25-48-85(6)49-26-50-86(7)51-27-52-87(8)53-28-54-88(9)55-29-56-89(10)57-30-58-90(11)59-31-60-91(12)61-32-62-92(13)63-33-64-93(14)65-34-66-94(15)67-35-68-95(16)69-36-70-96(17)71-37-72-97(18)73-38-74-98(19)75-39-76-99(20)77-40-78-100(21)79-80-101/h41,43,45,47,49,51,53,55,57,59,61,63,65,67,69,71,73,75,77,100-101H,22-40,42,44,46,48,50,52,54,56,58,60,62,64,66,68,70,72,74,76,78-80H2,1-21H3
InChI KeyKEVPZUBEAUSPNJ-UHFFFAOYSA-N
Isomeric SMILESCC(CCO)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C
Average Molecular Weight1382.3716
Monoisotopic Molecular Weight1381.27821987
Classification
DescriptionThis compound 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
  • Polyprenol skeleton
  • Dolichol
  • Fatty alcohol
  • Fatty acyl
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID4938490
ChEMBL IDNot Available
KEGG Compound IDC00381
Pubchem Compound ID6433320
Pubchem Substance IDNot Available
ChEBI ID16091
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05176
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDolichol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Dol-P-Man:Man(5)GlcNAc(2)-PP-Dol alpha-1,3-mannosyltransferaseALG3Q92685
UDP-N-acetylglucosamine--dolichyl-phosphate N-acetylglucosaminephosphotransferaseDPAGT1Q9H3H5
Dolichyl-phosphate beta-glucosyltransferaseALG5Q9Y673
Alpha-1,3/1,6-mannosyltransferase ALG2ALG2Q9H553
Dolichol-phosphate mannosyltransferaseDPM1O60762
Dolichol kinaseDOLKQ9UPQ8
Dolichyldiphosphatase 1DOLPP1Q86YN1
Probable dolichyl pyrophosphate Glc1Man9GlcNAc2 alpha-1,3-glucosyltransferaseALG8Q9BVK2
Dol-P-Glc:Glc(2)Man(9)GlcNAc(2)-PP-Dol alpha-1,2-glucosyltransferaseALG10Q5BKT4
Putative Dol-P-Glc:Glc(2)Man(9)GlcNAc(2)-PP-Dol alpha-1,2-glucosyltransferaseALG10BQ5I7T1
Dolichyl pyrophosphate Man9GlcNAc2 alpha-1,3-glucosyltransferaseALG6Q9Y672
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference