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Dolichol phosphate (YMDB00864)

Identification
YMDB IDYMDB00864
NameDolichol phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionDolichol phosphate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on Dolichol phosphate.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 triphosphate → Dolichol phosphate + hydron + CDP
Dolichol phosphate + Uridine diphosphate-N-acetylglucosamine → Uridine 5'-monophosphate + N-acetyl-α-D-glucosaminyl-diphosphodolichol
Guanosine diphosphate mannose + Dolichol phosphate → Guanosine diphosphate + dolichyl β-D-mannosyl phosphate
(Mannosyl)5-(N-acetylglucosaminyl)2-diphosphodolichol + dolichyl β-D-mannosyl phosphate → Dolichol 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ufs-9006000000-8fa91985de106ac27a82JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-c47fda1609169ecd31baJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2972000000-fd11c45c9967a687430aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kpi-4910000000-ca81e148de16a194714eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ss-9300000000-1cdfee9a400fec1d5d18JSpectraViewer
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

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. Dolichol kinase
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.
Protein Details
3. Dolichol-phosphate mannosyltransferase
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.
Protein Details
4. UDP-N-acetylglucosamine--dolichyl-phosphate N-acetylglucosaminephosphotransferase
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.
Protein Details
5. UDP-N-acetylglucosamine transferase subunit ALG13
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.
Protein Details
6. 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
7. Dolichyl-P-Man:Man(5)GlcNAc(2)-PP-dolichyl mannosyltransferase
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
Protein Details
8. 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
9. Dol-P-Man:Man(7)GlcNAc(2)-PP-Dol alpha-1,6-mannosyltransferase
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
Protein Details
10. Alpha-1,2-mannosyltransferase ALG9
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
Protein Details
11. 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