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Identification
YMDB IDYMDB00189
NameBeta-1,4-D-Mannosylchitobiosyldiphosphodolichol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionBeta-1,4-D-Mannosylchitobiosyldiphosphodolichol, also known as man-beta1->4glcnac-beta1->4glcnac-PP-dol, belongs to the class of organic compounds known as polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it. Beta-1,4-D-Mannosylchitobiosyldiphosphodolichol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
  • b-(1->4)-D-mannosylchitobiosyldiphosphodolichol
  • b-1,4-D-mannosylchitobiosyldiphosphodolichol
  • Beta-(1->4)-D-mannosylchitobiosyldiphosphodolichol
  • Beta-(1->4)-delta-mannosylchitobiosyldiphosphodolichol
  • beta-1,4-delta-mannosylchitobiosyldiphosphodolichol
  • Beta-D-mannosyldiacetylchitobiosyldiphosphodolichol
  • Beta-delta-mannosyldiacetylchitobiosyldiphosphodolichol
  • Man-beta1->4GlcNAc-beta1->4GlcNAc-PP-Dol
  • Β-1,4-D-mannosylchitobiosyldiphosphodolichol
  • N-[(2S,3R,4R,5S,6R)-4-Hydroxy-2-{[(2R,3S,4R,5R,6R)-4-hydroxy-6-{[hydroxy({[hydroxy({[(6E,10E,14E)-3,7,11,15,19-pentamethylicosa-6,10,14,18-tetraen-1-yl]oxy})phosphoryl]oxy})phosphoryl]oxy}-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)-5-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]ethanimidate
CAS numberNot Available
WeightAverage: 1089.1017
Monoisotopic: 1088.483445342
InChI KeyCMBCFQGXXHOGEH-LSMBNOQWSA-N
InChIInChI=1S/C47H82N2O22P2/c1-26(2)13-9-14-27(3)15-10-16-28(4)17-11-18-29(5)19-12-20-30(6)21-22-64-72(60,61)71-73(62,63)70-46-37(49-32(8)54)40(57)43(35(25-52)67-46)68-45-36(48-31(7)53)39(56)44(34(24-51)66-45)69-47-42(59)41(58)38(55)33(23-50)65-47/h13,15,17,19,30,33-47,50-52,55-59H,9-12,14,16,18,20-25H2,1-8H3,(H,48,53)(H,49,54)(H,60,61)(H,62,63)/b27-15+,28-17+,29-19+/t30?,33-,34-,35-,36-,37-,38-,39-,40-,41+,42+,43-,44-,45+,46-,47+/m1/s1
IUPAC Name{[(2R,3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}({[hydroxy({[(6E,10E,14E)-3,7,11,15,19-pentamethylicosa-6,10,14,18-tetraen-1-yl]oxy})phosphoryl]oxy})phosphinic acid
Traditional IUPAC Name[(2R,3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy({hydroxy[(6E,10E,14E)-3,7,11,15,19-pentamethylicosa-6,10,14,18-tetraen-1-yl]oxyphosphoryl}oxy)phosphinic acid
Chemical FormulaC47H82N2O22P2
SMILES[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@@]2([H])[C@]([H])(O[H])[C@@]([H])(N([H])C(=O)C([H])([H])[H])[C@]([H])(O[C@@]3([H])[C@]([H])(O[H])[C@@]([H])(N([H])C(=O)C([H])([H])[H])[C@@]([H])(OP(=O)(O[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])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])O[C@]3([H])C([H])([H])O[H])O[C@]2([H])C([H])([H])O[H])[C@@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenols
Direct ParentPolyprenyl phospho carbohydrates
Alternative Parents
Substituents
  • Polyprenyl phospho oligosaccharide
  • Polyprenyl phospho carbohydrate
  • Dolichyl diphosphate
  • Oligosaccharide phosphate
  • Polyprenyl monophosphate
  • Oligosaccharide
  • Polyprenyl phosphate skeleton
  • Sesterterpenoid
  • N-acyl-alpha-hexosamine
  • Glycosyl compound
  • O-glycosyl compound
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Acetal
  • Oxacycle
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Primary 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 Solubility0.15 g/LALOGPS
logP1.84ALOGPS
logP1.03ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area368.48 ŲChemAxon
Rotatable Bond Count29ChemAxon
Refractivity262.81 m³·mol⁻¹ChemAxon
Polarizability112.14 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Golgi
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
Beta-1,4-D-Mannosylchitobiosyldiphosphodolichol + Guanosine diphosphate mannosealpha-D-mannosyl-beta-D-mannosyldiacetylchitobiosyldiphosphodolichol + hydron + Guanosine diphosphate
Guanosine diphosphate mannose + N,N'-diacetylchitobiosyldiphosphodolicholBeta-1,4-D-Mannosylchitobiosyldiphosphodolichol
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18396
HMDB IDHMDB11673
Pubchem Compound ID24892765
Kegg IDC05860
ChemSpider ID26333131
FOODB IDFDB028362
Wikipedia IDNot Available
BioCyc IDD-GALACTOSYL-14-D-GALACTOSYL-14-D-

Enzymes

General function:
Involved in biosynthetic process
Specific function:
Participates in the formation of the lipid-linked precursor oligosaccharide for N-glycosylation. Involved in assembling the dolichol-pyrophosphate-GlcNAc(2)-Man(5) intermediate on the cytoplasmic surface of the ER
Gene Name:
ALG1
Uniprot ID:
P16661
Molecular weight:
51928.5
Reactions
GDP-mannose + chitobiosyldiphosphodolichol → GDP + beta-1,4-D-mannosylchitobiosyldiphosphodolichol.