Showing metabocard for Dolichyl b-D-glucosyl phosphate (BMDB0001054)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:40:27 UTC
Update Date2020-04-22 15:06:30 UTC
BMDB IDBMDB0001054
Secondary Accession Numbers
  • BMDB01054
Metabolite Identification
Common NameDolichyl b-D-glucosyl phosphate
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
ValueSource
Dolichyl b-D-glucosyl phosphoric acidGenerator
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
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • 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
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
BioavailabilityYesChemAxon
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, Positivesplash10-0002-9727600000-d38d6e1518a3a68d0771View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-8414129000-afb66cc4f90fc385e62bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0001900000-be2fd0839456e07b1706View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-4109400000-9e442a9d85d51464dbe2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-9101000000-36de47c7bd711fdcd51bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-2223900000-79cd2a11d46e0223c333View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fr-9245000000-c2b6be31b362b77ce9b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-9200000000-6fff84733fc82b56e1c2View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001054
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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 ReferencesNot Available