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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
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-phosphateD-Mannose 1-phosphate
D-Mannose 1-phosphate + GTP + hydronPyrophosphate + Guanosine diphosphate mannose
KEGG Reactions
GTP + hydron + D-Mannose 1-phosphatePyrophosphate + Guanosine diphosphate mannose
D-Mannose 1-phosphateD-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, 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
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
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

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.
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.
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.
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.