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alpha-D-mannosyl-beta-D-mannosyldiacetylchitobiosyldiphosphodolichol (YMDB00581)

Identification
YMDB IDYMDB00581
Namealpha-D-mannosyl-beta-D-mannosyldiacetylchitobiosyldiphosphodolichol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionalpha-D-mannosyl-beta-D-mannosyldiacetylchitobiosyldiphosphodolichol belongs to the class of organic compounds known as polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it. alpha-D-mannosyl-beta-D-mannosyldiacetylchitobiosyldiphosphodolichol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • alpha-1,3-D-Mannosyl-beta-1,4-D-mannosylchitobiosyldiphosphodolichol
  • alpha-D-Mannosyl-beta-D-mannosyl-diacetylchitobiosyldiphosphodolichol
  • Man-alpha1->3Man-beta1->4GlcNAc-beta1->4GlcNAc-PP-Dol
  • a-D-Mannosyl-b-D-mannosyldiacetylchitobiosyldiphosphodolichol
  • Α-D-mannosyl-β-D-mannosyldiacetylchitobiosyldiphosphodolichol
CAS numberNot Available
WeightAverage: 2272.9976
Monoisotopic: 2271.475272612
InChI KeyJUNJUMRONIXXFR-CGXDBECFSA-N
InChIInChI=1S/C128H212N2O27P2/c1-87(2)43-24-44-88(3)45-25-46-89(4)47-26-48-90(5)49-27-50-91(6)51-28-52-92(7)53-29-54-93(8)55-30-56-94(9)57-31-58-95(10)59-32-60-96(11)61-33-62-97(12)63-34-64-98(13)65-35-66-99(14)67-36-68-100(15)69-37-70-101(16)71-38-72-102(17)73-39-74-103(18)75-40-76-104(19)77-41-78-105(20)79-42-80-106(21)81-82-148-158(144,145)157-159(146,147)156-126-114(130-108(23)136)118(140)122(112(86-134)152-126)153-125-113(129-107(22)135)117(139)123(111(85-133)151-125)154-128-121(143)124(116(138)110(84-132)150-128)155-127-120(142)119(141)115(137)109(83-131)149-127/h43,45,47,49,51,53,55,57,59,61,63,65,67,69,71,73,75,77,79,106,109-128,131-134,137-143H,24-42,44,46,48,50,52,54,56,58,60,62,64,66,68,70,72,74,76,78,80-86H2,1-23H3,(H,129,135)(H,130,136)(H,144,145)(H,146,147)/b88-45+,89-47+,90-49+,91-51+,92-53-,93-55+,94-57+,95-59+,96-61+,97-63+,98-65+,99-67+,100-69+,101-71-,102-73+,103-75+,104-77+,105-79+/t106?,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119+,120+,121+,122-,123-,124+,125+,126-,127-,128+/m1/s1
IUPAC Name{[(2R,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-5-{[(2S,3S,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}({[hydroxy({[(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})phosphoryl]oxy})phosphinic acid
Traditional IUPAC Name[(2R,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-5-{[(2S,3S,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy({hydroxy[(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]oxyphosphoryl}oxy)phosphinic acid
Chemical FormulaC128H212N2O27P2
SMILESOC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](CO)O[C@@H](O[C@H]3[C@H](O)[C@@H](NC(C)=O)[C@@H](O[C@@H]3CO)O[C@H]3[C@H](O)[C@@H](NC(=O)C)[C@H](O[C@@H]3CO)OP(=O)(O)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]2O)[C@@H](O)[C@@H](O)[C@@H]1O
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
  • Polyterpenoid
  • Polyprenyl phospho carbohydrate
  • Dolichyl diphosphate
  • Oligosaccharide phosphate
  • Polyprenyl monophosphate
  • Oligosaccharide
  • Polyprenyl phosphate skeleton
  • N-acyl-alpha-hexosamine
  • O-glycosyl compound
  • 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
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Acetal
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0014 g/LALOGPS
logP7.63ALOGPS
logP24.16ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area447.63 ŲChemAxon
Rotatable Bond Count77ChemAxon
Refractivity652.27 m³·mol⁻¹ChemAxon
Polarizability266.93 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Golgi
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
Beta-1,4-D-Mannosylchitobiosyldiphosphodolichol + Guanosine diphosphate mannose → alpha-D-mannosyl-beta-D-mannosyldiacetylchitobiosyldiphosphodolichol + hydron + Guanosine diphosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableJSpectraViewer
References
References:
  • 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
  • Romero, P. A., Lussier, M., Sdicu, A. M., Bussey, H., Herscovics, A. (1997). "Ktr1p is an alpha-1,2-mannosyltransferase of Saccharomyces cerevisiae. Comparison of the enzymic properties of soluble recombinant Ktr1p and Kre2p/Mnt1p produced in Pichia pastoris." Biochem J 321 ( Pt 2):289-295.9020857
  • Lobsanov, Y. D., Romero, P. A., Sleno, B., Yu, B., Yip, P., Herscovics, A., Howell, P. L. (2004). "Structure of Kre2p/Mnt1p: a yeast alpha1,2-mannosyltransferase involved in mannoprotein biosynthesis." J Biol Chem 279:17921-17931.14752117
  • Lussier, M., Sdicu, A. M., Camirand, A., Bussey, H. (1996). "Functional characterization of the YUR1, KTR1, and KTR2 genes as members of the yeast KRE2/MNT1 mannosyltransferase gene family." J Biol Chem 271:11001-11008.8631921
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID28067
HMDB IDNot Available
Pubchem Compound ID24892766
Kegg IDC05861
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Glycolipid 2-alpha-mannosyltransferase
General function:
Involved in mannosyltransferase activity
Specific function:
Required for the attachment of the third mannose residue of O-linked saccharides
Gene Name:
KRE2
Uniprot ID:
P27809
Molecular weight:
51386.19922
Reactions
Protein Details
2. Alpha-1,2 mannosyltransferase KTR1
General function:
Involved in mannosyltransferase activity
Specific function:
Mannosyltransferase that transfers a mannose residue from GDP-mannose to a range of acceptors in vitro
Gene Name:
KTR1
Uniprot ID:
P27810
Molecular weight:
46021.69922
Reactions
Protein Details
3. Probable mannosyltransferase KTR2
General function:
Involved in mannosyltransferase activity
Specific function:
Involved in N-linked glycosylation
Gene Name:
KTR2
Uniprot ID:
P33550
Molecular weight:
50650.89844
Reactions
Protein Details
4. Probable mannosyltransferase KTR3
General function:
Involved in mannosyltransferase activity
Specific function:
Possible glycosyltransferase
Gene Name:
KTR3
Uniprot ID:
P38130
Molecular weight:
47482.0
Reactions
Protein Details
5. Probable mannosyltransferase YUR1
General function:
Involved in mannosyltransferase activity
Specific function:
Possible glycosyltransferase involved in N-linked glycosylation
Gene Name:
YUR1
Uniprot ID:
P26725
Molecular weight:
50835.60156
Reactions