Identification
YMDB IDYMDB00937
Namedolichyl D-mannosyl phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionDolichyl D-mannosyl phosphate is involved in dolichyl-diphosphooligosaccharide biosynthesis (N-linked glycosylation) pathway. N-linked glycosylation is an important process found in eukaryotes and archaea, and very rarely in bacteria. During this process certain oligosaccharides are attached to an asparagine residue in the polypeptide chain of the target protein. [Biocyc MANNOSYL-CHITO-DOLICHOL-BIOSYNTHESIS]
Structure
Thumb
Synonyms
  • Dolichyl D-mannosyl phosphate
  • Dolichyl phosphate D-mannose
  • Dolichyl D-mannosyl phosphoric acid
CAS numberNot Available
WeightAverage: 1624.4921
Monoisotopic: 1623.29737371
InChI KeyIPAOLVGASNLKMS-RABFXOQVSA-N
InChIInChI=1S/C106H175O9P/c1-82(2)41-22-42-83(3)43-23-44-84(4)45-24-46-85(5)47-25-48-86(6)49-26-50-87(7)51-27-52-88(8)53-28-54-89(9)55-29-56-90(10)57-30-58-91(11)59-31-60-92(12)61-32-62-93(13)63-33-64-94(14)65-34-66-95(15)67-35-68-96(16)69-36-70-97(17)71-37-72-98(18)73-38-74-99(19)75-39-76-100(20)77-40-78-101(21)79-80-113-116(111,112)115-106-105(110)104(109)103(108)102(81-107)114-106/h41,43,45,47,49,51,53,55,57,59,61,63,65,67,69,71,73,75,77,101-110H,22-40,42,44,46,48,50,52,54,56,58,60,62,64,66,68,70,72,74,76,78-81H2,1-21H3,(H,111,112)/b83-43+,84-45+,85-47+,86-49+,87-51-,88-53+,89-55+,90-57+,91-59+,92-61+,93-63+,94-65+,95-67+,96-69-,97-71+,98-73+,99-75+,100-77+/t101?,102-,103-,104+,105+,106?/m1/s1
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}({[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic 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]oxy[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphinic acid
Chemical FormulaC106H175O9P
SMILESOC[C@H]1OC(OP(O)(=O)OCCC(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)CC\C=C(/C)CCC=C(C)C)[C@@H](O)[C@@H](O)[C@@H]1O
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
  • Hexose monosaccharide
  • Monosaccharide phosphate
  • Dialkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0007 g/LALOGPS
logP9.12ALOGPS
logP30.47ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)1.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.91 ŲChemAxon
Rotatable Bond Count64ChemAxon
Refractivity521.95 m³·mol⁻¹ChemAxon
Polarizability209.08 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • endoplasmic reticulum
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
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 + dolichyl D-mannosyl phosphate ↔ 6-O-{alpha-D-mannosyl-(1->2)-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
protein + dolichyl D-mannosyl phosphate ↔ conjugated protein
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2530509000-e5f9fef0171eb1f7d2dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9031101000-bf96349fd299766d8cc4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-88f52928fa1d1bc675fdJSpectraViewer
MSMass Spectrum (Electron Ionization)Not AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
  • Banerjee, D. K., Carrasquillo, E. A., Hughey, P., Schutzbach, J. S., Martinez, J. A., Baksi, K. (2005). "In vitro phosphorylation by cAMP-dependent protein kinase up-regulates recombinant Saccharomyces cerevisiae mannosylphosphodolichol synthase." J Biol Chem 280:4174-4181.15548536
  • Lamani, E., Mewbourne, R. B., Fletcher, D. S., Maltsev, S. D., Danilov, L. L., Veselovsky, V. V., Lozanova, A. V., Grigorieva, N. Y., Pinsker, O. A., Xing, J., Forsee, W. T., Cheung, H. C., Schutzbach, J. S., Shibaev, V. N., Jedrzejas, M. J. (2006). "Structural studies and mechanism of Saccharomyces cerevisiae dolichyl-phosphate-mannose synthase: insights into the initial step of synthesis of dolichyl-phosphate-linked oligosaccharide chains in membranes of endoplasmic reticulum." Glycobiology 16:666-678.16549409
  • Tettelin, H., Agostoni Carbone, M. L., Albermann, K., Albers, M., Arroyo, J., Backes, U., Barreiros, T., Bertani, I., Bjourson, A. J., Bruckner, M., Bruschi, C. V., Carignani, G., Castagnoli, L., Cerdan, E., Clemente, M. L., Coblenz, A., Coglievina, M., Coissac, E., Defoor, E., Del Bino, S., Delius, H., Delneri, D., de Wergifosse, P., Dujon, B., Kleine, K., et, a. l. .. (1997). "The nucleotide sequence of Saccharomyces cerevisiae chromosome VII." Nature 387:81-84.9169869
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15809
HMDB IDNot Available
Pubchem Compound ID46878387
Kegg IDC03862
ChemSpider IDNot Available
FOODB IDNot Available
Wikipediadolichyl_D-mannosyl_phosphate
BioCyc IDNot Available

Enzymes

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 transferase activity, transferring glycosyl groups
Specific function:
Mannosyltransferase involved in glycosylphosphatidylinositol-anchor biosynthesis. Transfers the third mannose to Man2-GlcN-acyl-PI during GPI precursor assembly
Gene Name:
GPI10
Uniprot ID:
P30777
Molecular weight:
72564.89844
Reactions
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
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:
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
General function:
Involved in mannosyltransferase activity
Specific function:
Transfers mannose from Dol-P-mannose to Ser or Thr residues on proteins
Gene Name:
PMT3
Uniprot ID:
P47190
Molecular weight:
86322.0
Reactions
Dolichyl phosphate D-mannose + protein → dolichyl phosphate + O-D-mannosylprotein.
General function:
Involved in mannosyltransferase activity
Specific function:
Transfers mannose from Dol-P-mannose to Ser or Thr residues on proteins. Seems to be active on chitinase
Gene Name:
PMT2
Uniprot ID:
P31382
Molecular weight:
86869.0
Reactions
Dolichyl phosphate D-mannose + protein → dolichyl phosphate + O-D-mannosylprotein.
General function:
Involved in mannosyltransferase activity
Specific function:
Transfers mannose from Dol-P-mannose to Ser or Thr residues on proteins
Gene Name:
PMT6
Uniprot ID:
P42934
Molecular weight:
88025.39844
Reactions
Dolichyl phosphate D-mannose + protein → dolichyl phosphate + O-D-mannosylprotein.
General function:
Involved in mannosyltransferase activity
Specific function:
Transfers mannose from Dol-P-mannose to Ser or Thr residues on proteins. Seems to be active on chitinase
Gene Name:
PMT1
Uniprot ID:
P33775
Molecular weight:
92674.70313
Reactions
Dolichyl phosphate D-mannose + protein → dolichyl phosphate + O-D-mannosylprotein.
General function:
Involved in mannosyltransferase activity
Specific function:
Transfers mannose from Dol-P-mannose to Ser or Thr residues on proteins
Gene Name:
PMT5
Uniprot ID:
P52867
Molecular weight:
84775.20313
Reactions
Dolichyl phosphate D-mannose + protein → dolichyl phosphate + O-D-mannosylprotein.
General function:
Involved in mannosyltransferase activity
Specific function:
Transfers mannose from Dol-P-mannose to Ser or Thr residues on proteins. Seems to be active on GAS1
Gene Name:
PMT4
Uniprot ID:
P46971
Molecular weight:
87965.5
Reactions
Dolichyl phosphate D-mannose + protein → dolichyl phosphate + O-D-mannosylprotein.
General function:
Involved in mannosyltransferase activity
Specific function:
Transfers mannose from Dol-P-mannose to Ser or Thr residues on proteins
Gene Name:
PMT7
Uniprot ID:
Q06644
Molecular weight:
77568.79688
Reactions
Dolichyl phosphate D-mannose + protein → dolichyl phosphate + O-D-mannosylprotein.