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Record Information
Version3.6
Creation Date2006-05-22 14:17:29 UTC
Update Date2016-02-11 01:07:05 UTC
HMDB IDHMDB05176
Secondary Accession Numbers
  • HMDB05177
  • HMDB05178
  • HMDB05179
  • HMDB05180
  • HMDB05181
  • HMDB05182
  • HMDB05183
  • HMDB05184
  • HMDB05185
  • HMDB05186
  • HMDB12923
Metabolite Identification
Common 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 ).
Structure
Thumb
Synonyms
ValueSource
DolicholHMDB
Dolichol (C100)HMDB
Dolichol 20HMDB
Dolichol phosphateHMDB
Dolichyl phosphateHMDB
Chemical FormulaC100H164O
Average Molecular Weight1382.3716
Monoisotopic Molecular Weight1381.27821987
IUPAC Name(6E,10E,14E,18E,22Z,26E,30E,34E,38E,42E,46E,50E,54E,58Z,62E,66E,70E,74E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79-icosamethyloctaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78-nonadecaen-1-ol
Traditional Namedolichol
CAS Registry Number2067-66-5
SMILES
CC(CCO)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)CC\C=C(/C)CC\C=C(\C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C
InChI Identifier
InChI=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/b82-43+,83-45+,84-47+,85-49+,86-51-,87-53+,88-55+,89-57+,90-59+,91-61+,92-63+,93-65+,94-67+,95-69-,96-71+,97-73+,98-75+,99-77+
InChI KeyInChIKey=KEVPZUBEAUSPNJ-OYHKHEHLSA-N
Chemical Taxonomy
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
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 Solubility0.000217 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count59ChemAxon
Refractivity478.93 m3·mol-1ChemAxon
Polarizability189.17 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
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
  • Adrenal Gland
  • Fibroblasts
  • Spleen
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.031 +/- 0.01 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0017 +/- 0.00058 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023633
KNApSAcK IDNot Available
Chemspider ID4938490
KEGG Compound IDC00381
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDolichol
NuGOwiki LinkHMDB05176
Metagene LinkHMDB05176
METLIN ID6407
PubChem Compound6433320
PDB IDNot Available
ChEBI ID16091
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. [15741281 ]

Enzymes

General function:
Involved in biosynthetic process
Specific function:
Mannosylates Man(2)GlcNAc(2)-dolichol diphosphate and Man(1)GlcNAc(2)-dolichol diphosphate to form Man(3)GlcNAc(2)-dolichol diphosphate.
Gene Name:
ALG2
Uniprot ID:
Q9H553
Molecular weight:
47091.075
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Transfers mannose from GDP-mannose to dolichol monophosphate to form dolichol phosphate mannose (Dol-P-Man) which is the mannosyl donor in pathways leading to N-glycosylation, glycosyl phosphatidylinositol membrane anchoring, and O-mannosylation of proteins.
Gene Name:
DPM1
Uniprot ID:
O60762
Molecular weight:
29633.995
Reactions
Guanosine diphosphate mannose + Dolichol-20 → Guanosine diphosphate + Dolichyl beta-D-mannosyl phosphatedetails
Guanosine diphosphate mannose + Dolichol-20 → Guanosine diphosphate + Dolichyl phosphate D-mannosedetails
General function:
Involved in mannosyltransferase activity
Specific function:
Transfers mannosyl residues to the hydroxyl group of serine or threonine residues. Coexpression of both POMT1 and POMT2 is necessary for enzyme activity, expression of either POMT1 or POMT2 alone is insufficient.
Gene Name:
POMT1
Uniprot ID:
Q9Y6A1
Molecular weight:
82566.18
Reactions
Dolichyl phosphate D-mannose + protein → Dolichol-20 + O-D-mannosylproteindetails
General function:
Involved in mannosyltransferase activity
Specific function:
Transfers mannosyl residues to the hydroxyl group of serine or threonine residues. Coexpression of both POMT1 and POMT2 is necessary for enzyme activity, expression of either POMT1 or POMT2 alone is insufficient.
Gene Name:
POMT2
Uniprot ID:
Q9UKY4
Molecular weight:
84213.155
Reactions
Dolichyl phosphate D-mannose + protein → Dolichol-20 + O-D-mannosylproteindetails
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Not Available
Gene Name:
ALG5
Uniprot ID:
Q9Y673
Molecular weight:
33524.965
Reactions
Uridine diphosphate glucose + Dolichol-20 → Uridine 5'-diphosphate + Dolichyl b-D-glucosyl phosphatedetails
General function:
Involved in phospho-N-acetylmuramoyl-pentapeptide-transferase activity
Specific function:
Catalyzes the initial step in the synthesis of dolichol-P-P-oligosaccharides.
Gene Name:
DPAGT1
Uniprot ID:
Q9H3H5
Molecular weight:
46089.485
Reactions
Uridine diphosphate-N-acetylglucosamine + Dolichol-20 → Uridine 5'-monophosphate + N-acetyl-D-glucosaminyl-diphosphodolicholdetails
Uridine diphosphate-N-acetylglucosamine + Dolichol-20 → Uridine 5'-monophosphate + N-Acetyl-D-glucosaminyldiphosphodolicholdetails
General function:
Involved in catalytic activity
Specific function:
Required for efficient N-glycosylation. Necessary for maintaining optimal levels of dolichol-linked oligosaccharides. Hydrolyzes dolichyl pyrophosphate at a very high rate and dolichyl monophosphate at a much lower rate. Does not act on phosphatidate (By similarity).
Gene Name:
DOLPP1
Uniprot ID:
Q86YN1
Molecular weight:
22133.63
Reactions
Dolichyl diphosphate + Water → Dolichol-20 + Phosphoric aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Adds the first Dol-P-Man derived mannose in an alpha-1,3 linkage to Man5GlcNAc2-PP-Dol.
Gene Name:
ALG3
Uniprot ID:
Q92685
Molecular weight:
44369.995
Reactions
Dolichyl phosphate D-mannose + D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol → D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->3)-D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol + Dolichol-20details
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Adds the second glucose residue to the lipid-linked oligosaccharide precursor for N-linked glycosylation. Transfers glucose from dolichyl phosphate glucose (Dol-P-Glc) onto the lipid-linked oligosaccharide Glc(1)Man(9)GlcNAc(2)-PP-Dol (By similarity).
Gene Name:
ALG8
Uniprot ID:
Q9BVK2
Molecular weight:
60086.915
Reactions
Dolichyl b-D-glucosyl phosphate + D-Glc-alpha-(1->3)-D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-[D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->2)-D-Man-alpha-(1->6))-D-Man-alpha-(1->6)]-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol → Dolichol-20details
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Adds the third glucose residue to the lipid-linked oligosaccharide precursor for N-linked glycosylation. Transfers glucose from dolichyl phosphate glucose (Dol-P-Glc) onto the lipid-linked oligosaccharide Glc(2)Man(9)GlcNAc(2)-PP-Dol.
Gene Name:
ALG10
Uniprot ID:
Q5BKT4
Molecular weight:
55605.48
Reactions
Dolichyl b-D-glucosyl phosphate → Dolichol-20details
General function:
Lipid transport and metabolism
Specific function:
Involved in the synthesis of the sugar donor Dol-P-Man which is required in the synthesis of N-linked and O-linked oligosaccharides and for that of GPI anchors (By similarity).
Gene Name:
DOLK
Uniprot ID:
Q9UPQ8
Molecular weight:
59267.055
Reactions
Cytidine triphosphate + dolichol → CDP + Dolichol-20details
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Putative alpha-1,2-glucosyltransferase, which adds the third glucose residue to the lipid-linked oligosaccharide precursor for N-linked glycosylation. Transfers glucose from dolichyl phosphate glucose (Dol-P-Glc) onto the lipid-linked oligosaccharide Glc(2)Man(9)GlcNAc(2)-PP-Dol. When coupled to KCNH2 may reduce KCNH2 sensitivity to classic proarrhythmic drug blockade, possibly by mediating glycosylation of KCNH2.
Gene Name:
ALG10B
Uniprot ID:
Q5I7T1
Molecular weight:
55433.33
Reactions
Dolichyl b-D-glucosyl phosphate → Dolichol-20details
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Adds the first glucose residue to the lipid-linked oligosaccharide precursor for N-linked glycosylation. Transfers glucose from dolichyl phosphate glucose (Dol-P-Glc) onto the lipid-linked oligosaccharide Man(9)GlcNAc(2)-PP-Dol.
Gene Name:
ALG6
Uniprot ID:
Q9Y672
Molecular weight:
58119.89
Reactions
Dolichyl b-D-glucosyl phosphate + D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-[D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->2)-D-Man-alpha-(1->6))-D-Man-alpha-(1->6)]-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol → D-Glc-alpha-(1->3)-D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-[D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->2)-D-Man-alpha-(1->6))-D-Man-alpha-(1->6)]-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol + Dolichol-20details
General function:
Not Available
Specific function:
Adds the eighth mannose residue in an alpha-1,6 linkage onto the dolichol-PP-oligosaccharide precursor (dolichol-PP-Man(7)GlcNAc(2)) required for protein glycosylation.
Gene Name:
ALG12
Uniprot ID:
Q9BV10
Molecular weight:
54654.195
Reactions
Dolichyl phosphate D-mannose + D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol → D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->6))-D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol + Dolichol-20details
General function:
Not Available
Specific function:
Catalyzes the transfer of mannose from Dol-P-Man to lipid-linked oligosaccharides.
Gene Name:
ALG9
Uniprot ID:
Q9H6U8
Molecular weight:
69862.66
Reactions
Dolichyl phosphate D-mannose + D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->3)-D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol → D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol + Dolichol-20details
Dolichyl phosphate D-mannose + D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->6))-D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol → D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-[D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->2)-D-Man-alpha-(1->6))-D-Man-alpha-(1->6)]-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol + Dolichol-20details
General function:
Not Available
Specific function:
Regulates the biosynthesis of dolichol phosphate-mannose. Essential for the ER localization and stable expression of DPM1.
Gene Name:
DPM2
Uniprot ID:
O94777
Molecular weight:
Not Available
Reactions
Guanosine diphosphate mannose + Dolichol-20 → Guanosine diphosphate + Dolichyl phosphate D-mannosedetails
General function:
Not Available
Specific function:
Stabilizer subunit of the dolichol-phosphate-mannose synthase complex.
Gene Name:
DPM3
Uniprot ID:
Q9P2X0
Molecular weight:
Not Available
Reactions
Guanosine diphosphate mannose + Dolichol-20 → Guanosine diphosphate + Dolichyl phosphate D-mannosedetails