Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:00:08 UTC
HMDB IDHMDB0001513
Secondary Accession Numbers
  • HMDB01513
Metabolite Identification
Common NameDolichyl diphosphate
DescriptionThe term dolichol refers to a group of long-chain mostly unsaturated organic compounds consisting of a variable number of isoprene units that terminate with an alpha-saturated isoprenoid group containing an alcohol functional group. In the form of dolichol phosphate, dolichols help facilitate protein N-glycosylation (Wikipedia). Glycosylation of asparagine residues in proteins is carried out by transferring glucose from a dolichyl diphosphate oligosaccharide (PMID: 7379786 ).
Structure
Data?1599602835
Synonyms
ValueSource
Dolichol diphosphateKegg
Dolichol diphosphoric acidGenerator
Dolichyl diphosphoric acidGenerator
Dolichol pyrophosphateHMDB
Dolichyl pyrophosphateHMDB
Pyrophosphoryl dolicholHMDB
Dolichyl diphosphateHMDB
Chemical Formula(C5H8)nC20H38O7P2
Average Molecular WeightNot Available
Monoisotopic Molecular WeightNot Available
IUPAC Namedolichol pyrophosphate
Traditional Namedolichol pyrophosphate
CAS Registry Number37247-98-6
SMILES
CC(CCOP(O)(=O)OP(O)(O)=O)CC\C=C(\C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C
InChI Identifier
InChI=1S/C25H46O7P2/c1-21(2)11-7-12-22(3)13-8-14-23(4)15-9-16-24(5)17-10-18-25(6)19-20-31-34(29,30)32-33(26,27)28/h11,13,15,17,25H,7-10,12,14,16,18-20H2,1-6H3,(H,29,30)(H2,26,27,28)/b22-13+,23-15+,24-17-
InChI KeyMXGLYEVGJRXBTP-QOLULZROSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as polyprenyl diphosphates. These are prenol lipids in which the diphosphate group is linked to one end of the polyprenol moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenols
Direct ParentPolyprenyl diphosphates
Alternative Parents
Substituents
  • Polyprenyl diphosphate
  • Dolichyl diphosphate
  • Polyprenyl monophosphate
  • Sesterterpenoid
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.64 g/LALOGPS
logP5.21ALOGPS
logS-5.6ALOGPS
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+205.62530932474
DeepCCS[M-H]-203.22830932474
DeepCCS[M-2H]-236.11230932474
DeepCCS[M+Na]+211.53830932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolichyl diphosphate 10V, Positive-QTOFsplash10-006x-1319560000-708df26fea5e6e5614852019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolichyl diphosphate 20V, Positive-QTOFsplash10-0006-4429100000-b4180d49ab72f97027cd2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolichyl diphosphate 40V, Positive-QTOFsplash10-0006-4449000000-0d19b360327c0b2132b52019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolichyl diphosphate 10V, Negative-QTOFsplash10-014i-0400090000-09ed3e8ebf064013ea392019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolichyl diphosphate 20V, Negative-QTOFsplash10-004i-9201000000-982c4e7291f91755e0c02019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolichyl diphosphate 40V, Negative-QTOFsplash10-004i-9000000000-9fcecdd44b53bc65fe732019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolichyl diphosphate 10V, Negative-QTOFsplash10-01b9-0000590000-ff40a651a148f6c740392021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolichyl diphosphate 20V, Negative-QTOFsplash10-05r0-9800080000-210bd881391d3e7f86112021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolichyl diphosphate 40V, Negative-QTOFsplash10-0a4i-4900000000-bb700d3d1e704cc8cb9c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolichyl diphosphate 10V, Positive-QTOFsplash10-00di-2205490000-452e15fea66a1a585f732021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolichyl diphosphate 20V, Positive-QTOFsplash10-0006-4259100000-9ee831d9b538b00af7072021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolichyl diphosphate 40V, Positive-QTOFsplash10-000f-1957000000-f2d839d16273b5d22ada2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022667
KNApSAcK IDNot Available
Chemspider ID24846867
KEGG Compound IDC00621
BioCyc IDDolichol-PP
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6290
PubChem Compound24892721
PDB IDNot Available
ChEBI ID15750
Food Biomarker OntologyNot Available
VMH IDDOLDP_L
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Staneloni RJ, Ugalde RA, Leloir LF: Addition of glucose to dolichyl diphosphate oligosaccharide and transfer to protein. Eur J Biochem. 1980 Apr;105(2):275-8. doi: 10.1111/j.1432-1033.1980.tb04498.x. [PubMed:7379786 ]

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 + Phosphatedetails
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