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Record Information
Version	2.0
Creation Date	2012-05-31 13:52:38 -0600
Update Date	2015-06-03 15:54:07 -0600
Secondary Accession Numbers	ECMDB01436
Identification
Name:	D-Mannose 1-phosphate
Description	D-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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaf1ed480> Close
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.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Monosaccharide phosphates
Alternative Parents	Hexoses Monoalkyl phosphates Oxanes Secondary alcohols Polyols Oxacyclic compounds Primary alcohols Organic oxides Hydrocarbon derivatives
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 Framework	Aliphatic heteromonocyclic compounds
External Descriptors	mannose phosphate (CHEBI:35374 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 32.3 g/L ALOGPS logP -2 ALOGPS logP -3.1 ChemAxon logS -0.91 ALOGPS pKa (Strongest Acidic) 1.16 ChemAxon pKa (Strongest Basic) -3 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 156.91 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 46.8 m³·mol⁻¹ ChemAxon Polarizability 20.68 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	D-Mannose 1-phosphate <> Mannose 6-phosphate Guanosine diphosphate + Hydrogen ion + D-Mannose 1-phosphate > Guanosine diphosphate mannose + Phosphate Guanosine diphosphate mannose + Water > Guanosine monophosphate +2 Hydrogen ion + D-Mannose 1-phosphate Guanosine triphosphate + D-Mannose 1-phosphate <> Pyrophosphate + Guanosine diphosphate mannose Mannose 6-phosphate <> D-Mannose 1-phosphate Guanosine diphosphate mannose + Water > Hydrogen ion + Guanosine monophosphate + D-Mannose 1-phosphate Hydrogen ion + D-Mannose 1-phosphate + Guanosine triphosphate > Guanosine diphosphate mannose + Pyrophosphate α-D-mannose 6-phosphate > D-Mannose 1-phosphate D-Mannose 1-phosphate + Guanosine triphosphate + Hydrogen ion > Pyrophosphate + Guanosine diphosphate mannose Guanosine triphosphate + D-Mannose 1-phosphate <> Pyrophosphate + Guanosine diphosphate mannose Guanosine triphosphate + D-Mannose 1-phosphate <> Pyrophosphate + Guanosine diphosphate mannose
SMPDB Pathways:	Mannose Metabolism PW000822
KEGG Pathways:	Amino sugar and nucleotide sugar metabolism ec00520 Fructose and mannose metabolism ec00051 Metabolic pathways eco01100
EcoCyc Pathways:	GDP-mannose biosynthesis PWY-5659
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-MS (6 TMS) splash10-014i-1893000000-0ec9e139257029be0d07 View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-014i-1893000000-0ec9e139257029be0d07 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0002-9110000000-ee60e23a7f8053dae6d3 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive splash10-0fsi-3930250000-c69e78c38872d5ee6b95 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0002-9240000000-4057005941a73b47e92b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0002-9240000000-2b520b8d7520453613e5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0002-9100000000-adafd3ed58bf5371e4a1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0a6s-9480000000-6d21f499da6e13bbe38d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9110000000-68aeffe1ebca2d4d4362 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-dfc211275bafe42581ae View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View 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
Links
External Links:	Resource Link CHEBI ID 35374 HMDB ID HMDB06330 Pubchem Compound ID 644175 Kegg ID C00636 ChemSpider ID 559210 Wikipedia ID Mannose_1-phosphate BioCyc ID MANNOSE-1P EcoCyc ID MANNOSE-1P

Enzymes