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dolichyl phosphate (YMDB00941)

Identification
YMDB IDYMDB00941
Namedolichyl phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptiondolichyl phosphate belongs to the class of organic compounds known as dolichyl monophosphates. These are polyprenyl compounds consisting of a monophosphate group substituted by a dolichyl moiety. dolichyl phosphate is a moderately acidic compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • dolichol monophosphate
  • Dolichol phosphate
  • Dolicholmonophosphate
  • Dolichyl monophosphate
  • Dolichyl phosphate
  • Dolichyl phosphoric acid
CAS number12698-55-4
WeightAverage: 1462.3515
Monoisotopic: 1461.24455028
InChI KeyANYZAZFGBISMDO-OYHKHEHLSA-N
InChIInChI=1S/C100H165O4P/c1-81(2)41-22-42-82(3)43-23-44-83(4)45-24-46-84(5)47-25-48-85(6)49-26-50-86(7)51-27-52-87(8)53-28-54-88(9)55-29-56-89(10)57-30-58-90(11)59-31-60-91(12)61-32-62-92(13)63-33-64-93(14)65-34-66-94(15)67-35-68-95(16)69-36-70-96(17)71-37-72-97(18)73-38-74-98(19)75-39-76-99(20)77-40-78-100(21)79-80-104-105(101,102)103/h41,43,45,47,49,51,53,55,57,59,61,63,65,67,69,71,73,75,77,100H,22-40,42,44,46,48,50,52,54,56,58,60,62,64,66,68,70,72,74,76,78-80H2,1-21H3,(H2,101,102,103)/b82-43+,83-45+,84-47+,85-49+,86-51-,87-53+,88-55+,89-57+,90-59+,91-61+,92-63+,93-65+,94-67+,95-69-,96-71+,97-73+,98-75+,99-77+
IUPAC Name{[(6E,10E,14E,18E,22Z,26E,30E,34E,38E,42E,46E,50E,54E,58Z,62E,66E,70E,74E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79-icosamethyloctaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78-nonadecaen-1-yl]oxy}phosphonic acid
Traditional IUPAC Name[(6E,10E,14E,18E,22Z,26E,30E,34E,38E,42E,46E,50E,54E,58Z,62E,66E,70E,74E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79-icosamethyloctaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78-nonadecaen-1-yl]oxyphosphonic acid
Chemical FormulaC100H165O4P
SMILESCC(CCOP(O)(O)=O)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(\C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(\C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C
Chemical Taxonomy
Description belongs to the class of organic compounds known as dolichyl monophosphates. These are polyprenyl compounds consisting of a monophosphate group substituted by a dolichyl moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenols
Direct ParentDolichyl monophosphates
Alternative Parents
Substituents
  • Polyterpenoid
  • Polyprenyl monophosphate
  • Dolichyl monophosphate
  • 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 Solubility0.00041 g/LALOGPS
logP9.64ALOGPS
logP32.5ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)1.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count61ChemAxon
Refractivity489.81 m³·mol⁻¹ChemAxon
Polarizability193.63 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • endoplasmic reticulum
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
N-Glycan biosynthesisPW002501 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
N-Glycan biosynthesisec00510 Map00510
SMPDB ReactionsNot Available
KEGG Reactions
Dolichol-20 + Cytidine triphosphate → dolichyl phosphate + CDP + hydron
dolichyl phosphate + Guanosine diphosphate mannose → Guanosine diphosphate + dolichyl D-mannosyl phosphate
dolichyl D-mannosyl phosphate → dolichyl phosphate + hydron + mannan
6-(alpha-D-glucosaminyl)-O-acyl-1-phosphatidyl-1D-myo-inositol + dolichyl D-mannosyl phosphate ↔ dolichyl phosphate + 6-O-[alpha-D-mannosyl-(1->4)-alpha-D-glucosaminyl]-O-acyl-1-phosphatidyl-1D-myo-inositol
6-O-{2-O-[(2-aminoethyl)phosphoryl]-alpha-D-mannosyl-(1->4)-alpha-D-glucosaminyl}-O-acyl-1-phosphatidyl-1D-myo-inositol + dolichyl D-mannosyl phosphate ↔ dolichyl phosphate + 6-O-{alpha-D-mannosyl-(1->6)-2-O-[(2-aminoethyl)phosphoryl]-alpha-D-mannosyl-(1->4)-alpha-D-glucosaminyl}-O-acyl-1-phosphatidyl-1D-myo-inositol
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-8000900000-8396e36ebdd4ca5b6c91JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-64f50373038323e9ada7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-fb19c66886e627db76bfJSpectraViewer
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
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Fernandez, F., Shridas, P., Jiang, S., Aebi, M., Waechter, C. J. (2002). "Expression and characterization of a human cDNA that complements the temperature-sensitive defect in dolichol kinase activity in the yeast sec59-1 mutant: the enzymatic phosphorylation of dolichol and diacylglycerol are catalyzed by separate CTP-mediated kinase activities in Saccharomyces cerevisiae." Glycobiology 12:555-562.12213788
  • Orlowski, J., Machula, K., Janik, A., Zdebska, E., Palamarczyk, G. (2007). "Dissecting the role of dolichol in cell wall assembly in the yeast mutants impaired in early glycosylation reactions." Yeast 24:239-252.17397129
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16214
HMDB IDNot Available
Pubchem Compound ID24892715
Kegg IDC00110
ChemSpider IDNot Available
FOODB IDNot Available
Wikipediadolichyl_phosphate
BioCyc IDNot Available

Enzymes

Protein Details
1. 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
2. Dolichyldiphosphatase
General function:
Involved in catalytic activity
Specific function:
Non-essential protein which is 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
Gene Name:
CAX4
Uniprot ID:
P53223
Molecular weight:
27648.80078
Reactions
Dolichyl diphosphate + H(2)O → dolichyl phosphate + 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. GPI mannosyltransferase 2
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Mannosyltransferase involved in glycosylphosphatidylinositol-anchor biosynthesis. Transfers the second mannose to the glycosylphosphatidylinositol during GPI precursor assembly
Gene Name:
GPI18
Uniprot ID:
P38211
Molecular weight:
50772.19922
Reactions
Protein Details
6. GPI mannosyltransferase 1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Mannosyltransferase involved in glycosylphosphatidylinositol-anchor biosynthesis. Transfers the first alpha-1,4-mannose to GlcN-acyl-PI during GPI precursor assembly. Required for cell wall integrity
Gene Name:
GPI14
Uniprot ID:
P47088
Molecular weight:
47165.89844