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D-Mannose 1-phosphate (YMDB00386)

Identification
YMDB IDYMDB00386
NameD-Mannose 1-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-Mannose 1-phosphate, also known as mannose 1-phosphoric acid, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. D-Mannose 1-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Mannose 1-phosphate exists in both E. coli (prokaryote) and yeast (eukaryote). D-mannose 1-phosphate can be biosynthesized from mannose 6-phosphate through the action of the enzyme phosphomannomutase. In yeast, D-mannose 1-phosphate is involved in the metabolic pathway called the mannose metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-(dihydrogen phosphate)-D-Mannopyranose
  • 1-(dihydrogen phosphate)-delta-Mannopyranose
  • alpha-D-Mannose 1-phosphate
  • alpha-delta-Mannose 1-phosphate
  • D-mannose 1-phosphates
  • D-mannose-1-phosphate
  • delta-mannose 1-phosphates
  • delta-mannose-1-phosphate
  • Mannose 1-phosphate
  • Mannose 1-phosphate-Mannopyranose
  • mannose-1-P
  • Mannose 1-phosphoric acid
  • D-Mannose 1-phosphoric acid
CAS number27251-84-9
WeightAverage: 260.1358
Monoisotopic: 260.029718526
InChI KeyHXXFSFRBOHSIMQ-QTVWNMPRSA-N
InChIInChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6?/m1/s1
IUPAC Name{[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional IUPAC NameD-mannose 1-phosphate
Chemical FormulaC6H13O9P
SMILES[H]OC([H])([H])[C@@]1([H])OC([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 monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Oxane
  • Alkyl phosphate
  • Phosphoric acid ester
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Primary 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 Solubility32.3 g/LALOGPS
logP-2ALOGPS
logP-3.1ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)1.16ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.8 m³·mol⁻¹ChemAxon
Polarizability20.68 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
SMPDB Reactions
Mannose 6-phosphate → D-Mannose 1-phosphate
D-Mannose 1-phosphate + GTP + hydron → Pyrophosphate + Guanosine diphosphate mannose
KEGG Reactions
GTP + hydron + D-Mannose 1-phosphate → Pyrophosphate + Guanosine diphosphate mannose
D-Mannose 1-phosphate ↔ D-mannose 6-phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-014i-1893000000-0ec9e139257029be0d07JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1893000000-0ec9e139257029be0d07JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9110000000-ee60e23a7f8053dae6d3JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0fsi-3930250000-c69e78c38872d5ee6b95JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6s-9480000000-6d21f499da6e13bbe38dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-68aeffe1ebca2d4d4362JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-dfc211275bafe42581aeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9240000000-4057005941a73b47e92bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9240000000-2b520b8d7520453613e5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9100000000-adafd3ed58bf5371e4a1JSpectraViewer
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
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • 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
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID35374
HMDB IDHMDB06330
Pubchem Compound ID644175
Kegg IDC03812
ChemSpider ID24604707
FOODB IDFDB023892
Wikipedia IDMannose_1-phosphate
BioCyc IDMANNOSE-1P

Enzymes

Protein Details
1. Ectonucleotide pyrophosphatase/phosphodiesterase 1
General function:
Involved in catalytic activity
Specific function:
Mediates extracellular nucleotide derived phosphate hydrolysis along with NPP2 and PHO5
Gene Name:
NPP1
Uniprot ID:
P25353
Molecular weight:
84733.20313
Reactions
A dinucleotide + H(2)O → 2 mononucleotides.
Protein Details
2. Ectonucleotide pyrophosphatase/phosphodiesterase 2
General function:
Involved in catalytic activity
Specific function:
Mediates extracellular nucleotide derived phosphate hydrolysis along with NPP1 and PHO5
Gene Name:
NPP2
Uniprot ID:
P39997
Molecular weight:
57354.10156
Reactions
A dinucleotide + H(2)O → 2 mononucleotides.
Protein Details
3. Mannose-1-phosphate guanyltransferase
General function:
Involved in transferase activity
Specific function:
Involved in cell wall synthesis where it is required for glycosylation. Involved in cell cycle progression through cell- size checkpoint
Gene Name:
MPG1
Uniprot ID:
P41940
Molecular weight:
39565.60156
Reactions
GTP + alpha-D-mannose 1-phosphate → diphosphate + GDP-mannose.
Protein Details
4. Phosphomannomutase
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.