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Identification
YMDB IDYMDB00831
Namealpha-D-mannose 1-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionα-D-Mannose 1-phosphate belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. α-D-Mannose 1-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). α-D-Mannose 1-phosphate exists in both E. coli (prokaryote) and yeast (eukaryote).
Structure
Thumb
Synonyms
  • 1-(dihydrogen phosphate)-D-Mannopyranose
  • 1-(dihydrogen phosphate)-delta-Mannopyranose
  • 1-O-phosphono-alpha-D-mannopyranose
  • alpha-D-mannose 1-phosphate
  • alpha-delta-Mannose 1-phosphate
  • D-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
  • 1-O-Phosphono-a-D-mannopyranose
  • 1-O-Phosphono-α-D-mannopyranose
  • a-D-Mannose 1-phosphate
  • a-D-Mannose 1-phosphoric acid
  • alpha-D-Mannose 1-phosphoric acid
  • Α-D-mannose 1-phosphoric acid
  • D-Mannose 1-phosphoric acid
CAS number27251-84-9
WeightAverage: 260.1358
Monoisotopic: 260.029718526
InChI KeyHXXFSFRBOHSIMQ-RWOPYEJCSA-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{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional IUPAC Nameα-D-mannose 1-phosphate
Chemical FormulaC6H13O9P
SMILESOC[C@H]1O[C@H](OP(O)(O)=O)[C@@H](O)[C@@H](O)[C@@H]1O
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
Polarizability20.79 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 ReactionsNot Available
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, Positivesplash10-0002-9110000000-ee60e23a7f8053dae6d3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9240000000-0a7885872856fe43526bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9240000000-b437590c213fb263989dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0532-9100000000-97504a02d14244b901cbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-9360000000-98c3aee1d36863dc12abJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-92ad15ffc9eae3eed039JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-dfc211275bafe42581aeJSpectraViewer
References
References:
  • 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
  • Hashimoto, H., Sakakibara, A., Yamasaki, M., Yoda, K. (1997). "Saccharomyces cerevisiae VIG9 encodes GDP-mannose pyrophosphorylase, which is essential for protein glycosylation." J Biol Chem 272:16308-16314.9195935
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18205
HMDB IDHMDB06330
Pubchem Compound ID25245607
Kegg IDC00636
ChemSpider ID24604707
FOODB IDNot Available
Wikipediaalpha-D-mannose_1-phosphate
BioCyc IDMANNOSE-1P

Enzymes

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.