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Identification
YMDB IDYMDB00581
Namealpha-D-mannosyl-beta-D-mannosyldiacetylchitobiosyldiphosphodolichol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionalpha-D-mannosyl-beta-D-mannosyldiacetylchitobiosyldiphosphodolichol is an extremely weak basic (essentially neutral) compound (based on its pKa). alpha-D-mannosyl-beta-D-mannosyldiacetylchitobiosyldiphosphodolichol may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
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
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 mannosealpha-D-mannosyl-beta-D-mannosyldiacetylchitobiosyldiphosphodolichol + hydron + Guanosine diphosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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

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
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
General function:
Involved in mannosyltransferase activity
Specific function:
Involved in N-linked glycosylation
Gene Name:
KTR2
Uniprot ID:
P33550
Molecular weight:
50650.89844
Reactions
General function:
Involved in mannosyltransferase activity
Specific function:
Possible glycosyltransferase
Gene Name:
KTR3
Uniprot ID:
P38130
Molecular weight:
47482.0
Reactions
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