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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:46 UTC
HMDB IDHMDB01054
Secondary Accession NumbersNone
Metabolite Identification
Common NameDolichyl b-D-glucosyl phosphate
DescriptionDolichyl β-D-glucosyl phosphate is a polyisoprenyl phosphate monosaccharide. Biosynthesis is by Glucosyltransferase in liver mitochondria. (PubMed ID 6450044 ).
Structure
Thumb
Synonyms
ValueSource
Dolichol monophosphate glucoseHMDB
Dolichyl b-delta-glucosyl phosphateHMDB
Dolichyl beta-D-glucosyl phosphateHMDB
Dolichyl beta-delta-glucosyl phosphateHMDB
Dolichyl monophosphate glucoseHMDB
Dolichyl phosphate glucoseHMDB
Dolichylphosphoryl glucoseHMDB
Chemical FormulaC21H39O9P
Average Molecular Weight466.5027
Monoisotopic Molecular Weight466.233169358
IUPAC Name{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}({[(6Z)-3,7,11-trimethyldodeca-6,10-dien-1-yl]oxy})phosphinic acid
Traditional Namedolichyl phosphate glucose
CAS Registry Number220496-27-5
SMILES
OC[C@H]1O[C@@H](OP(=O)(O)OCCC(C)CC\C=C(\C)CCC=C(C)C)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C21H39O9P/c1-14(2)7-5-8-15(3)9-6-10-16(4)11-12-28-31(26,27)30-21-20(25)19(24)18(23)17(13-22)29-21/h7,9,16-25H,5-6,8,10-13H2,1-4H3,(H,26,27)/b15-9-/t16?,17-,18-,19+,20-,21+/m1/s1
InChI KeyInChIKey=RHJMCOLWMXJOGE-ZTZGTLKASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Farsesane sesquiterpenoid
  • Sesquiterpenoid
  • Monosaccharide phosphate
  • Dialkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Saccharide
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of N-Glycan biosynthesis
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 Solubility0.62 mg/mLALOGPS
logP1.78ALOGPS
logP2.25ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)1.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.91 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity117.31 m3·mol-1ChemAxon
Polarizability48.82 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
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
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 IDFDB022394
KNApSAcK IDNot Available
Chemspider ID17216044
KEGG Compound IDC01246
BioCyc IDNot Available
BiGG ID1809280
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01054
Metagene LinkHMDB01054
METLIN ID5969
PubChem Compound22833557
PDB IDNot Available
ChEBI ID15812
References
Synthesis ReferenceRush, Jeffrey S.; Van Leyen, Klaus; Ouerfelli, Ouathek; Wolucka, Beata; Waechter, Charles J. Transbilayer movement of Glc-P-dolichol and its function as a glucosyl donor: protein-mediated transport of a water-soluble analog into sealed ER vesicles from pig brain. Glycobiology (1998), 8(12), 1195-1205.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gateau O, Morelis R, Louisot P: Glucosyltransferase activities in liver mitochondria. I. Biosynthesis of dolichyl[14C]glucosyl phosphate and [14C]glucosylceramide. Eur J Biochem. 1980 Nov;112(1):193-201. [6450044 ]

Enzymes

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 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:
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