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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 08:00:30 UTC
HMDB IDHMDB0001054
Secondary Accession Numbers
  • HMDB01054
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 KeyRHJMCOLWMXJOGE-ZTZGTLKASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Farsesane sesquiterpenoid
  • Hexose monosaccharide
  • Monosaccharide phosphate
  • Dialkyl phosphate
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Primary alcohol
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

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 Solubility0.62 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity117.31 m³·mol⁻¹ChemAxon
Polarizability48.82 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2489500000-ee4f5c268ead36d45bbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-6790000000-335bdfa9a636c87f56d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5961000000-a91c7ccdc6413bbba7a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-2553900000-b96efe52d60699a8d378View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9231100000-2bbc2deb52045a357ff5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9000000000-e8e7a4fcaced53795fb5View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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
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. [PubMed: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