Dolichyl b-D-glucosyl phosphate (YMDB00241)

Identification
YMDB IDYMDB00241
NameDolichyl b-D-glucosyl phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionDolichyl b-D-glucosyl phosphate, also known as dolichol monophosphate glucose, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Dolichyl b-D-glucosyl phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • Dolichol monophosphate glucose
  • Dolichyl b-D-glucosyl phosphate
  • Dolichyl b-D-glucosyl phosphic acid
  • Dolichyl b-delta-glucosyl phosphate
  • Dolichyl b-delta-glucosyl phosphic acid
  • dolichyl beta-D-glucosyl phosphate
  • dolichyl beta-delta-glucosyl phosphate
  • Dolichyl monophosphate glucose
  • Dolichyl phosphate glucose
  • Dolichylphosphoryl glucose
  • Dolichyl b-D-glucosyl phosphoric acid
CAS number220496-27-5
WeightAverage: 466.5027
Monoisotopic: 466.233169358
InChI KeyRHJMCOLWMXJOGE-NRNKQJRZSA-N
InChIInChI=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
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 IUPAC Namedolichyl phosphate glucose
Chemical FormulaC21H39O9P
SMILES[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(OP(=O)(O[H])OC([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]
Chemical Taxonomy
Description 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
  • 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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Polarizability49.65 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
N-Glycan biosynthesisPW002501 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
N-Glycan biosynthesisec00510 Map00510
SMPDB Reactions
(Mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + Dolichyl b-D-glucosyl phosphate → Glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + Dolichol phosphate + hydron
Uridine diphosphate glucose + Dolichol phosphate → Uridine 5'-diphosphate + Dolichyl b-D-glucosyl phosphate
Glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + Dolichyl b-D-glucosyl phosphate → (Glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + Dolichol phosphate + hydron
(Glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + Dolichyl b-D-glucosyl phosphate → hydron + Dolichol phosphate + (glucosyl)3(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9727600000-d38d6e1518a3a68d0771JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-8414129000-afb66cc4f90fc385e62bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2489500000-ee4f5c268ead36d45bbfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-6790000000-335bdfa9a636c87f56d3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5961000000-a91c7ccdc6413bbba7a7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-2553900000-b96efe52d60699a8d378JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9231100000-2bbc2deb52045a357ff5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9000000000-e8e7a4fcaced53795fb5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0001900000-be2fd0839456e07b1706JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-4109400000-9e442a9d85d51464dbe2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-9101000000-36de47c7bd711fdcd51bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-2223900000-79cd2a11d46e0223c333JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fr-9245000000-c2b6be31b362b77ce9b9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-9200000000-6fff84733fc82b56e1c2JSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Rush, 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 p
External Links:
ResourceLink
CHEBI ID15812
HMDB IDHMDB01054
Pubchem Compound ID439457
Kegg IDC01246
ChemSpider ID17216044
FOODB IDFDB022394
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Dolichyl-phosphate beta-glucosyltransferase
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
UDP-glucose + dolichyl phosphate = UDP + dolichyl beta-D-glucosyl phosphate
Gene Name:
ALG5
Uniprot ID:
P40350
Molecular weight:
38346.39844
Reactions
UDP-glucose + dolichyl phosphate → UDP + dolichyl beta-D-glucosyl phosphate.
Protein Details
2. Alpha-1,2 glucosyltransferase ALG10
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:
DIE2
Uniprot ID:
P50076
Molecular weight:
61807.0
Reactions
Protein Details
3. Dolichyl pyrophosphate Glc1Man9GlcNAc2 alpha-1,3-glucosyltransferase
General function:
protein N-linked glycosylation
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.
Gene Name:
ALG8
Uniprot ID:
P40351
Molecular weight:
67384.29
Reactions
Protein Details
4. Dolichyl pyrophosphate Man9GlcNAc2 alpha-1,3-glucosyltransferase
General function:
protein N-linked glycosylation
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:
Q12001
Molecular weight:
62782.275
Reactions