Identification
YMDB IDYMDB00242
NameMannose 6-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionMannose 6-phosphate (M6P) is an intermediate in carboydrates biosynthesis. M6P is converted to fructose 6-phosphate by mannose phosphate isomerase. M6P is a targeting signal for acid hydrolase precursor proteins that are destined for transport to lysosomes. The M6P tag is added to such proteins in the cis-Golgi apparatus. Specifically, in a reaction involving uridine diphosphate (UDP) and N-acetylglucosamine, the enzyme UDP-N-acetylglucosamine:N-acetylglucosaminyl-1-phosphotransferase catalyzes the N-linked glycosylation of asparagine residues with M6P. Once appropriately marked with the M6P targeting signal, these proteins are moved to the trans-Golgi. There, the M6P moiety is recognized by mannose 6-phosphate receptor (MPR) proteins. The MPRs traffic in vesicles to the lysosome via an endosome. [Wikipedia]
Structure
Thumb
Synonyms
  • alpha-D-mannose-6-P
  • alpha-D-mannose-6-phosphate
  • alpha-delta-mannose-6-P
  • alpha-delta-mannose-6-phosphate
  • D-Mannose 6-phosphate
  • delta-Mannose 6-phosphate
  • Man-6-p
  • Mannose 6-phosphate
  • Mannose 6-phosphic acid
  • Mannose-6-phosphate
  • Mannose 6-phosphoric acid
  • Mannose-6-phosphate dilithium salt
  • Mannose-6-phosphate disodium salt
  • Mannose-6-phosphate sodium salt, (D)-isomer
CAS number3672-15-9
WeightAverage: 260.1358
Monoisotopic: 260.029718526
InChI KeyNBSCHQHZLSJFNQ-RWOPYEJCSA-N
InChIInChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6-/m1/s1
IUPAC Name{[(2R,3S,4S,5S,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Namemannose 6 phosphate
Chemical FormulaC6H13O9P
SMILES[H]O[C@]1([H])O[C@]([H])(C([H])([H])OP(=O)(O[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 hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexose phosphates
Alternative Parents
Substituents
  • Hexose phosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Oxane
  • Phosphoric acid ester
  • Hemiacetal
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility31.4 g/LALOGPS
logP-2.1ALOGPS
logP-3.1ChemAxon
logS-0.92ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.8 m³·mol⁻¹ChemAxon
Polarizability20.99 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Amino sugar and nucleotide sugar metabolismPW002413 ThumbThumb?image type=greyscaleThumb?image type=simple
Mannose MetabolismPW002391 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Amino sugar and nucleotide sugar metabolismec00520 Map00520
Fructose and mannose metabolismec00051 Map00051
SMPDB Reactions
D-Mannose + Adenosine triphosphatehydron + ADP + Mannose 6-phosphate
Mannose 6-phosphateBeta-D-Fructose 6-phosphate
Mannose 6-phosphateD-Mannose 1-phosphate
Adenosine triphosphate + D-MannoseADP + Mannose 6-phosphate
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9740000000-a6e81224fb97751dc2e6JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001i-2533590000-b6a62e882bfffed3184aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0007-3490000000-734a88a9b3fd55b3e43fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052b-9300000000-2c63b28f70b6b2eb75a1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00l2-9000000000-5406aea843f73d03563cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0490000000-94ea79ec673f4688b7a0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dm-5940000000-c649262446626dcb8d6eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uka-9800000000-aae2cb792906d2dec6cdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-8290000000-8e20219f94b3fe964e38JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-b19b64f5cb4124047bafJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-ecb75a44e3d25affdf31JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6s-9060000000-b446300429049a22bea4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-d5aaca13a836cb9f1725JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dm-0970000000-40dbaf3d3c72cf65bf47JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-7900000000-00bc03290b6c0bfb7f84JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-9000000000-7a6ff6606f1dbc2f0ae4JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Pascual, C.; Herrera, L. Use of permeabilized yeast cells as a system of enzyme immobilization. Its use for the preparation of mannose 6-phosphate. Folia Microbiologica (Prague, Czech Republic) (1981), 26(2), 103-6.
External Links:
ResourceLink
CHEBI ID49728
HMDB IDHMDB01078
Pubchem Compound ID65127
Kegg IDC00275
ChemSpider ID25057696
FOODB IDFDB022411
WikipediaMannose_6-phosphate
BioCyc IDMANNOSE-6P

Enzymes

General function:
Involved in ATP binding
Specific function:
Main glucose phosphorylating enzyme. May play a regulatory role in both induction and repression of gene expression by glucose
Gene Name:
HXK2
Uniprot ID:
P04807
Molecular weight:
53942.0
Reactions
ATP + D-hexose → ADP + D-hexose 6-phosphate.
ATP + D-fructose → ADP + D-fructose 1-phosphate
General function:
Involved in ATP binding
Specific function:
ATP + D-hexose = ADP + D-hexose 6-phosphate
Gene Name:
Not Available
Uniprot ID:
Q06204
Molecular weight:
48968.80078
Reactions
ATP + D-hexose → ADP + D-hexose 6-phosphate.
General function:
Involved in ATP binding
Specific function:
ATP + D-hexose = ADP + D-hexose 6-phosphate
Gene Name:
HXK1
Uniprot ID:
P04806
Molecular weight:
53737.89844
Reactions
ATP + D-hexose → ADP + D-hexose 6-phosphate.
ATP + D-fructose → ADP + D-fructose 1-phosphate
General function:
Involved in mannose-6-phosphate isomerase activity
Specific function:
Involved in the synthesis of the GDP-mannose and dolichol-phosphate-mannose required for a number of critical mannosyl transfer reactions
Gene Name:
PMI40
Uniprot ID:
P29952
Molecular weight:
48188.30078
Reactions
D-mannose 6-phosphate → D-fructose 6-phosphate.
General function:
Involved in ATP binding
Specific function:
Putative glucokinase involved in phosphorylation of aldohexoses and glucose uptake. Involved in sporulation. Required for the full activation of the early meiotic inducer IME1
Gene Name:
EMI2
Uniprot ID:
Q04409
Molecular weight:
55920.30078
Reactions
ATP + D-glucose → ADP + D-glucose 6-phosphate.
General function:
Involved in ATP binding
Specific function:
Two isoenzymes, hexokinase-1 and hexokinase-2, can phosphorylate keto- and aldohexoses in yeast, whereas a third isoenzyme, GLK, is specific for aldohexoses. All glucose phosphorylating enzymes are involved in glucose uptake
Gene Name:
GLK1
Uniprot ID:
P17709
Molecular weight:
55376.89844
Reactions
ATP + D-glucose → ADP + D-glucose 6-phosphate.
General function:
Involved in catalytic activity
Specific function:
Involved in the synthesis of the GDP-mannose and dolichol-phosphate-mannose required for a number of critical mannosyl transfer reactions
Gene Name:
SEC53
Uniprot ID:
P07283
Molecular weight:
29062.69922
Reactions
Alpha-D-mannose 1-phosphate → D-mannose 6-phosphate.