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Identification
YMDB IDYMDB00966
NameD-mannose 6-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-mannose 6-phosphate 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. D-mannose 6-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). D-mannose 6-phosphate may be a unique S. cerevisiae (yeast) metabolite. In yeast, D-mannose 6-phosphate is involved in the metabolic pathway called the mannose metabolism pathway.
Structure
Thumb
Synonyms
  • 6-O-phosphono-D-mannose
  • alpha-D-mannose-6-P
  • alpha-D-mannose-6-phosphate
  • alpha-delta-mannose-6-P
  • alpha-delta-mannose-6-phosphate
  • D-Mannose 6-phosphate
  • D-Mannose, 6-(dihydrogen phosphate)
  • delta-Mannose 6-phosphate
  • Man-6-p
  • Mannose 6-phosphate
  • Mannose 6-phosphic acid
  • Mannose-6-phosphate
  • D-Mannose 6-phosphoric acid
  • Mannose-6-phosphate disodium salt
  • Mannose-6-phosphate sodium salt, (D)-isomer
  • Mannose-6-phosphate dilithium salt
CAS number3672-15-9
WeightAverage: 260.1358
Monoisotopic: 260.029718526
InChI KeyNBSCHQHZLSJFNQ-QTVWNMPRSA-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)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Namemannose 6-phosphate
Chemical FormulaC6H13O9P
SMILESOC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O
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
Polarizability20.59 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
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 ReactionsNot Available
KEGG Reactions
Adenosine triphosphate + D-MannoseD-mannose 6-phosphate + hydron + ADP
D-mannose 6-phosphateFructose 6-phosphate
D-Mannose 1-phosphateD-mannose 6-phosphate
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 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
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
  • Roux, C., Lee, J. H., Jeffery, C. J., Salmon, L. (2004). "Inhibition of type I and type II phosphomannose isomerases by the reaction intermediate analogue 5-phospho-D-arabinonohydroxamic acid supports a catalytic role for the metal cofactor." Biochemistry 43:2926-2934.15005628
  • Foret, J., de Courcy, B., Gresh, N., Piquemal, J. P., Salmon, L. (2009). "Synthesis and evaluation of non-hydrolyzable D-mannose 6-phosphate surrogates reveal 6-deoxy-6-dicarboxymethyl-D-mannose as a new strong inhibitor of phosphomannose isomerases." Bioorg Med Chem 17:7100-7107.19783448
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17369
HMDB IDHMDB01078
Pubchem Compound ID65127
Kegg IDC00275
ChemSpider ID25057696
FOODB IDFDB030772
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:
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 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.