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Dolichol-20 (YMDB00928)

Identification
YMDB IDYMDB00928
NameDolichol-20
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionDolichol-20, also known as dolichol, belongs to the class of organic compounds known as polyprenols. These are prenols with more than 4 consecutive isoprene units. Dolichol-20 is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • Dolichol
  • Dolichol (C100)
  • Dolichol 20
  • Dolichol phosphate
  • Dolichyl phosphate
CAS number2067-66-5
WeightAverage: 1382.3716
Monoisotopic: 1381.27821987
InChI KeyKEVPZUBEAUSPNJ-OYHKHEHLSA-N
InChIInChI=1S/C100H164O/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)79-80-101/h41,43,45,47,49,51,53,55,57,59,61,63,65,67,69,71,73,75,77,100-101H,22-40,42,44,46,48,50,52,54,56,58,60,62,64,66,68,70,72,74,76,78-80H2,1-21H3/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-ol
Traditional IUPAC Namedolichol
Chemical FormulaC100H164O
SMILESCC(CCO)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 polyprenols. These are prenols with more than 4 consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenols
Direct ParentPolyprenols
Alternative Parents
Substituents
  • Polyterpenoid
  • Dolichol
  • Polyprenol skeleton
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • 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 Solubility0.00022 g/LALOGPS
logP9.62ALOGPS
logP32.63ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)17.11ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count59ChemAxon
Refractivity478.93 m³·mol⁻¹ChemAxon
Polarizability189.17 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • lipid particle
  • cytoplasm
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
KEGG Reactions
Dolichol-20 + Cytidine triphosphate → dolichyl phosphate + CDP + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0109000000-1d33270fa2d9629618b1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-4729120122-b87e1de86451067517adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08g0-5937231223-89f3a3e1e0e5abdd4712JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-e1d022d2820ff21e0303JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-0009000000-05d1724ee18bf7d978e0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-2119000000-c41f2ad0a7afc9bdeb3dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f89-0009000000-971cebd9197bb7821df0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0009000000-f504389989e492cdb03cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1098000000-030b73616f2591714248JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0039000000-134bbcf91a821214ee28JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w29-2269101001-95e411f157ea81561f8aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0hpw-8931848465-7032896457f9bc4826d5JSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Juchimiuk, M., Pasikowska, M., Zatorska, E., Laudy, A. E., Smolenska-Sym, G., Palamarczyk, G. (2010). "Defect in dolichol-dependent glycosylation increases sensitivity of Saccharomyces cerevisiae towards anti-fungal drugs." Yeast 27:637-645.20602334
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16091
HMDB IDHMDB05176
Pubchem Compound ID6433320
Kegg IDC00381
ChemSpider ID4938490
FOODB IDFDB023633
WikipediaDolichol
BioCyc IDDOLICHOL-GROUP

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. 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
4. 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
5. 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.