You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB00864
NameDolichol phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionDolichol phosphate, also known as dolichol-p, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Dolichol phosphate is possibly neutral.
Structure
Thumb
Synonyms
  • dolichol monophosphate
  • Dolichol-P
  • dolichol-phosphate
  • Dolichol-PO4
  • dolichyl-phosphate
  • Dolychol phosphate
  • Dolichol phosphoric acid
CAS number34457-14-2
WeightAverage: 304.3621
Monoisotopic: 304.180345928
InChI KeyDZHSRPJGCZHWOM-NTEUORMPSA-N
InChIInChI=1S/C15H29O4P/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-19-20(16,17)18/h7,9,15H,5-6,8,10-12H2,1-4H3,(H2,16,17,18)/b14-9+
IUPAC NameNot Available
Traditional IUPAC NameNot Available
Chemical FormulaC15H29O4P
SMILES[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]
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
  • Farsesane sesquiterpenoid
  • Sesquiterpenoid
  • 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 DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.048 g/LALOGPS
logP3.4ALOGPS
logS-3.8ALOGPS
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
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
Dolichol-20 + Cytidine triphosphateDolichol phosphate + hydron + CDP
Dolichol phosphate + Uridine diphosphate-N-acetylglucosamineUridine 5'-monophosphate + N-acetyl-α-D-glucosaminyl-diphosphodolichol
Guanosine diphosphate mannose + Dolichol phosphateGuanosine diphosphate + dolichyl β-D-mannosyl phosphate
(Mannosyl)5-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-mannosyl phosphateDolichol phosphate + hydron + (Mannosyl)6-(N-acetylglucosaminyl)2-diphosphodolichol
(Mannosyl)6-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-mannosyl phosphate(Mannosyl)7-(N-acetylglucosaminyl)2-diphosphodolichol + Dolichol phosphate + hydron
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, Positivesplash10-0002-9630000000-2363aa5efd80171e1ae6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1496000000-ec1df72c4987cf00bd11JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-7950000000-ed6057f6c271c64a2f44JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06di-9700000000-4d5d06a74044e737dbccJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ufr-8009000000-fca69e87dde06919337cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-03b07e3a8c2213183b79JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-ea573660632a9aabc66cJSpectraViewer
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Bickel, T., Lehle, L., Schwarz, M., Aebi, M., Jakob, C. A. (2005). "Biosynthesis of lipid-linked oligosaccharides in Saccharomyces cerevisiae: Alg13p and Alg14p form a complex required for the formation of GlcNAc(2)-PP-dolichol." J Biol Chem 280:34500-34506.16100113
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB06353
Pubchem Compound ID5280322
Kegg IDC00110
ChemSpider ID4444045
FOODB IDFDB023901
WikipediaDolichol
BioCyc IDNot Available

Enzymes

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.
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
Involved in the synthesis of the sugar donor Dol-P-Man which is required in the synthesis of N-linked and O-linked oligosaccharides and for that of GPI anchors. It is required for spore germination. Has an essential role in cellular metabolism
Gene Name:
SEC59
Uniprot ID:
P20048
Molecular weight:
58905.39844
Reactions
CTP + dolichol → CDP + dolichyl phosphate.
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Transfers mannose from GDP-mannose to dolichol monophosphate to form dolichol phosphate mannose (Dol-P-Man) which is the mannosyl donor in pathways leading to N-glycosylation, glycosyl phosphatidylinositol membrane anchoring, and O- mannosylation of proteins
Gene Name:
DPM1
Uniprot ID:
P14020
Molecular weight:
30362.0
Reactions
GDP-mannose + dolichyl phosphate → GDP + dolichyl D-mannosyl phosphate.
General function:
Involved in phospho-N-acetylmuramoyl-pentapeptide-transferase activity
Specific function:
Catalyzes the initial step in the synthesis of dolichol- P-P-oligosaccharides
Gene Name:
ALG7
Uniprot ID:
P07286
Molecular weight:
50367.39844
Reactions
UDP-N-acetyl-D-glucosamine + dolichyl phosphate → UMP + N-acetyl-D-glucosaminyl-diphosphodolichol.
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Involved in protein N-glycosylation. Essential for the second step of the dolichol-linked oligosaccharide pathway
Gene Name:
ALG13
Uniprot ID:
P53178
Molecular weight:
22660.90039
Reactions
UDP-N-acetyl-D-glucosamine + N-acetyl-D-glucosaminyl-diphosphodolichol → UDP + N,N'-diacetylchitobiosyl-diphosphodolichol.
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
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Adds the first Dol-P-Man derived mannose in an alpha-1,3 linkage to Man(5)GlcNAc(2)-PP-Dol. Sensitive to H.mrakii HM-1 killer toxin
Gene Name:
ALG3
Uniprot ID:
P38179
Molecular weight:
52860.39844
Reactions
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
General function:
protein N-linked glycosylation
Specific function:
Adds the eighth mannose residue in an alpha-1,6 linkage onto the dolichol-PP-oligosaccharide precursor (dolichol-PP-Man(7)GlcNAc(2)) required for protein glycosylation.
Gene Name:
ALG12
Uniprot ID:
P53730
Molecular weight:
62671.87
Reactions
General function:
protein glycosylation
Specific function:
Catalyzes the transfer of mannose from Dol-P-Man to lipid-linked oligosaccharides.
Gene Name:
ALG9
Uniprot ID:
P53868
Molecular weight:
63776.03
Reactions
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