Record Information
Version2.0
Creation Date2012-05-31 13:52:38 -0600
Update Date2015-06-03 15:54:07 -0600
Secondary Accession Numbers
  • ECMDB01436
Identification
Name:D-Mannose 1-phosphate
DescriptionD-Mannose 1-phosphate is a normal metabolite intermediate in the Fructose and mannose metabolism, and substrate of phosphomannomutase 1 (PMM, EC: 5.4.2.8), an enzyme necessary for the synthesis of GDP-mannose. PMM converts mannose 6-phosphate to mannose-1-phosphate, which is required for the synthesis of GDP-mannose, a substrate for dolichol-linked oligosaccharide synthesis.
Structure
Thumb
Synonyms:
  • 1-(Dihydrogen phosphate)-D-Mannopyranose
  • 1-(Dihydrogen phosphate)-delta-Mannopyranose
  • 1-(Dihydrogen phosphate)-δ-mannopyranose
  • 1-(Dihydrogen phosphoric acid)-D-mannopyranose
  • 1-(Dihydrogen phosphoric acid)-delta-mannopyranose
  • 1-(Dihydrogen phosphoric acid)-δ-mannopyranose
  • a-D-Mannose 1-phosphate
  • a-D-Mannose 1-phosphoric acid
  • a-delta-Mannose 1-phosphate
  • a-delta-Mannose 1-phosphoric acid
  • a-δ-Mannose 1-phosphate
  • a-δ-Mannose 1-phosphoric acid
  • Alpha-D-Mannose 1-phosphate
  • alpha-D-Mannose 1-phosphoric acid
  • Alpha-delta-Mannose 1-phosphate
  • alpha-delta-Mannose 1-phosphoric acid
  • D-Mannose 1-phosphates
  • D-Mannose 1-phosphoric acid
  • D-Mannose-1-phosphate
  • D-Mannose-1-phosphoric acid
  • Delta-Mannose 1-phosphates
  • Delta-Mannose-1-phosphate
  • delta-Mannose-1-phosphoric acid
  • Man1P
  • Mannose 1-phosphate
  • Mannose 1-phosphate-Mannopyranose
  • Mannose 1-phosphoric acid
  • Mannose 1-phosphoric acid-mannopyranose
  • Mannose-1-P
  • Mannose-1-phosphate
  • Mannose-1-phosphoric acid
  • α-D-Mannose 1-phosphate
  • α-D-Mannose 1-phosphoric acid
  • α-δ-Mannose 1-phosphate
  • α-δ-Mannose 1-phosphoric acid
  • δ-Mannose 1-phosphates
  • δ-Mannose-1-phosphate
  • δ-Mannose-1-phosphoric acid
Chemical Formula:C6H13O9P
Weight:Average: 260.1358
Monoisotopic: 260.029718526
InChI Key:HXXFSFRBOHSIMQ-QTVWNMPRSA-N
InChI:InChI=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
CAS number:27251-84-9
IUPAC Name:{[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional IUPAC Name:D-mannose 1-phosphate
SMILES:OC[C@H]1OC(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
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Reactions:
SMPDB Pathways:
Mannose MetabolismPW000822 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-014i-1893000000-0ec9e139257029be0d07View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1893000000-0ec9e139257029be0d07View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9110000000-ee60e23a7f8053dae6d3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0fsi-3930250000-c69e78c38872d5ee6b95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9240000000-4057005941a73b47e92bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9240000000-2b520b8d7520453613e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9100000000-adafd3ed58bf5371e4a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6s-9480000000-6d21f499da6e13bbe38dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-68aeffe1ebca2d4d4362View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-dfc211275bafe42581aeView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Korner C, Lehle L, von Figura K: Abnormal synthesis of mannose 1-phosphate derived carbohydrates in carbohydrate-deficient glycoprotein syndrome type I fibroblasts with phosphomannomutase deficiency. Glycobiology. 1998 Feb;8(2):165-71. Pubmed: 9451026
  • Orvisky E, Stubblefield B, Long RT, Martin BM, Sidransky E, Krasnewich D: Phosphomannomutase activity in congenital disorders of glycosylation type Ia determined by direct analysis of the interconversion of mannose-1-phosphate to mannose-6-phosphate by high-pH anion-exchange chromatography with pulsed amperometric detection. Anal Biochem. 2003 Jun 1;317(1):12-8. Pubmed: 12729595
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Van Schaftingen E, Jaeken J: Phosphomannomutase deficiency is a cause of carbohydrate-deficient glycoprotein syndrome type I. FEBS Lett. 1995 Dec 27;377(3):318-20. Pubmed: 8549746
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID35374
HMDB IDHMDB06330
Pubchem Compound ID644175
Kegg IDC00636
ChemSpider ID559210
Wikipedia IDMannose_1-phosphate
BioCyc IDMANNOSE-1P
EcoCyc IDMANNOSE-1P

Enzymes

General function:
Involved in nucleotidyltransferase activity
Specific function:
Involved in the biosynthesis of the capsular polysaccharide colanic acid
Gene Name:
manC
Uniprot ID:
P24174
Molecular weight:
53016
Reactions
GTP + alpha-D-mannose 1-phosphate = diphosphate + GDP-mannose.
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
Involved in the biosynthesis of the capsular polysaccharide colanic acid
Gene Name:
manB
Uniprot ID:
P24175
Molecular weight:
50462
Reactions
Alpha-D-mannose 1-phosphate = D-mannose 6-phosphate.
General function:
Involved in hydrolase activity, acting on acid anhydrides, in phosphorus-containing anhydrides
Specific function:
Catalyzes the hydrolysis of GDP-mannose. Can also use other substrates, catalyzing the hydrolysis of the pyrophosphate bond, releasing a nucleoside monophosphate and a phosphorylated moiety, depending on the substrate
Gene Name:
nudK
Uniprot ID:
P37128
Molecular weight:
21749
Reactions
GDP-mannose + H(2)O = GMP + mannose-1-phosphate.