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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:42 UTC
HMDB IDHMDB01513
Secondary Accession NumbersNone
Metabolite Identification
Common NameDolichyl diphosphate
DescriptionThe glycosylation of asparagine residues in proteins is known to occur by transfer from a dolichyl diphosphate oligosaccharide containing glucose. The addition of all three glucoses to the dolichyl diphosphate oligosaccharide occur with dolichyl phosphate glucose as donor.(http://www.blackwell-synergy.com/links/doi/10.1111/j.1432-1033.1980.tb04498.x/abs/).
Structure
Thumb
Synonyms
  1. Dolichyl diphosphate
Chemical FormulaC12H26O7P2
Average Molecular Weight344.2782
Monoisotopic Molecular Weight344.11537621
IUPAC Name[({[(7E)-3,8-dimethyldec-7-en-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional Name{[(7E)-3,8-dimethyldec-7-en-1-yl]oxy(hydroxy)phosphoryl}oxyphosphonic acid
CAS Registry Number37247-98-6
SMILES
CC\C(C)=C\CCCC(C)CCOP(O)(=O)OP(O)(O)=O
InChI Identifier
InChI=1S/C12H26O7P2/c1-4-11(2)7-5-6-8-12(3)9-10-18-21(16,17)19-20(13,14)15/h7,12H,4-6,8-10H2,1-3H3,(H,16,17)(H2,13,14,15)/b11-7+
InChI KeyFFBTVOMODCZDNV-YRNVUSSQSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassOrganic Oxoanionic Compounds
Sub ClassOrganic Pyrophosphates
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Acyclic Alkene
  • Isoprene
  • Organic Phosphite
  • Phosphoric Acid Ester
Direct ParentOrganic Pyrophosphates
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of N-Glycan biosynthesis
ApplicationNot Available
Cellular locations
  • 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 Solubility0.64ALOGPS
logP1.95ALOGPS
logP3.1ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity81.43 m3·mol-1ChemAxon
Polarizability33.28 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDFDB022667
KNApSAcK IDNot Available
Chemspider ID13748633
KEGG Compound IDC00621
BioCyc IDCPD-224
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01513
Metagene LinkHMDB01513
METLIN ID6290
PubChem Compound5462166
PDB IDNot Available
ChEBI ID15750
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in dolichyl-diphosphooligosaccharide-protein glycotransferase activity
Specific function:
Essential subunit of the N-oligosaccharyl transferase (OST) complex which catalyzes the transfer of a high mannose oligosaccharide from a lipid-linked oligosaccharide donor to an asparagine residue within an Asn-X-Ser/Thr consensus motif in nascent polypeptide chains.
Gene Name:
RPN1
Uniprot ID:
P04843
Molecular weight:
68568.81
Reactions
Dolichyl diphosphooligosaccharide + [protein]-L-asparagine → Dolichyl diphosphate + a glycoprotein with the oligosaccharide chain attached by N-beta-D-glycosyl linkage to a protein L-asparaginedetails
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 dolichyl-diphosphooligosaccharide-protein glycotransferase activity
Specific function:
Essential subunit of the N-oligosaccharyl transferase (OST) complex which catalyzes the transfer of a high mannose oligosaccharide from a lipid-linked oligosaccharide donor to an asparagine residue within an Asn-X-Ser/Thr consensus motif in nascent polypeptide chains.
Gene Name:
DDOST
Uniprot ID:
P39656
Molecular weight:
50701.205
Reactions
Dolichyl diphosphooligosaccharide + [protein]-L-asparagine → Dolichyl diphosphate + a glycoprotein with the oligosaccharide chain attached by N-beta-D-glycosyl linkage to a protein L-asparaginedetails
General function:
Involved in dolichyl-diphosphooligosaccharide-protein glycotransferase activity
Specific function:
Essential subunit of the N-oligosaccharyl transferase (OST) complex which catalyzes the transfer of a high mannose oligosaccharide from a lipid-linked oligosaccharide donor to an asparagine residue within an Asn-X-Ser/Thr consensus motif in nascent polypeptide chains.
Gene Name:
RPN2
Uniprot ID:
P04844
Molecular weight:
67722.73
Reactions
Dolichyl diphosphooligosaccharide + [protein]-L-asparagine → Dolichyl diphosphate + a glycoprotein with the oligosaccharide chain attached by N-beta-D-glycosyl linkage to a protein L-asparaginedetails
General function:
Involved in oligosaccharyl transferase activity
Specific function:
Catalytic subunit of the N-oligosaccharyl transferase (OST) complex which catalyzes the transfer of a high mannose oligosaccharide from a lipid-linked oligosaccharide donor to an asparagine residue within an Asn-X-Ser/Thr consensus motif in nascent polypeptide chains. N-glycosylation occurs cotranslationally and the complex associates with the Sec61 complex at the channel-forming translocon complex that mediates protein translocation across the endoplasmic reticulum (ER). SST3A seems to be involved in complex substrate specificity. STT3A is present in the majority of OST complexes and mediates cotranslational N-glycosylation of most sites on target proteins, while STT3B-containing complexes are required for efficient cotranslational glycosylation and mediate glycosylation of sites that have been skipped by STT3A.
Gene Name:
STT3A
Uniprot ID:
P46977
Molecular weight:
80528.83
Reactions
Dolichyl diphosphooligosaccharide + [protein]-L-asparagine → Dolichyl diphosphate + a glycoprotein with the oligosaccharide chain attached by N-beta-D-glycosyl linkage to a protein L-asparaginedetails
Dolichyl diphosphooligosaccharide + Protein asparagine → Dolichyl diphosphate + Glycoprotein with the oligosaccharide chain attached by N-glycosyl linkage to protein L-asparaginedetails
Protein asparagine + → Dolichyl diphosphate + details
General function:
Involved in dolichyl-diphosphooligosaccharide-protein g
Specific function:
Essential subunit of the N-oligosaccharyl transferase (OST) complex which catalyzes the transfer of a high mannose oligosaccharide from a lipid-linked oligosaccharide donor to an asparagine residue within an Asn-X-Ser/Thr consensus motif in nascent polypeptide chains. N-glycosylation occurs cotranslationally and the complex associates with the Sec61 complex at the channel-forming translocon complex that mediates protein translocation across the endoplasmic reticulum (ER). Loss of the DAD1 protein triggers apoptosis (By similarity).
Gene Name:
DAD1
Uniprot ID:
P61803
Molecular weight:
12496.55
Reactions
Dolichyl diphosphooligosaccharide + [protein]-L-asparagine → Dolichyl diphosphate + a glycoprotein with the oligosaccharide chain attached by N-beta-D-glycosyl linkage to a protein L-asparaginedetails
General function:
Involved in oligosaccharyl transferase activity
Specific function:
Catalytic subunit of the N-oligosaccharyl transferase (OST) complex which catalyzes the transfer of a high mannose oligosaccharide from a lipid-linked oligosaccharide donor to an asparagine residue within an Asn-X-Ser/Thr consensus motif in nascent polypeptide chains. N-glycosylation occurs cotranslationally and the complex associates with the Sec61 complex at the channel-forming translocon complex that mediates protein translocation across the endoplasmic reticulum (ER). STT3B is present in a small subset of OST complexes and mediates both cotranslational and post-translational N-glycosylation of target proteins: STT3B-containing complexes are required for efficient cotranslational glycosylation and while they are less competent than STT3A-containing complexes for cotranslational glycosylation, they have the ability to mediate glycosylation of some nascent sites that are not accessible for STT3A. STT3B-containing complexes also act post-translationally and mediate modification of skipped glycosylation sites in unfolded proteins. Plays a role in ER-associated degradation (ERAD) pathway that mediates ubiquitin-dependent degradation of misfolded endoplasmic reticulum proteins by mediating N-glycosylation of unfolded proteins, which are then recognized by the ERAD pathway and targeted for degradation. Mediates glycosylation of the disease variant AMYL-TTR 'Asp-38' of TTR at 'Asn-118', leading to its degradation.
Gene Name:
STT3B
Uniprot ID:
Q8TCJ2
Molecular weight:
93673.495
Reactions
Dolichyl diphosphooligosaccharide + [protein]-L-asparagine → Dolichyl diphosphate + a glycoprotein with the oligosaccharide chain attached by N-beta-D-glycosyl linkage to a protein L-asparaginedetails
Dolichyl diphosphooligosaccharide + Protein asparagine → Dolichyl diphosphate + Glycoprotein with the oligosaccharide chain attached by N-glycosyl linkage to protein L-asparaginedetails
Protein asparagine + → Dolichyl diphosphate + details