Mannitol 1-phosphate (ECMDB21434) (M2MDB001829)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (4)Transporters (2)XML
Proteins (179)
Record Information
Version2.0
Creation Date2012-08-09 09:16:14 -0600
Update Date2015-06-03 17:21:29 -0600
Secondary Accession Numbers
  • ECMDB21434
Identification
Name:Mannitol 1-phosphate
DescriptionMannitol-1-phosphate is a sugar alcohol. Mannitol-1-phosphate dehydrogenase (EC 1.1.1.17) reduces fructose 6-phosphate into mannitol 1-phosphate, in the mannitol cycle of organisms such as Lactobacillus plantarum, a lactic acid bacterium found in many fermented food products and in the gastrointestinal tract of mammals. (HMDB) This redox reaction also occurs in E. coli, catalyzed by mannitol-1-phosphate 5-dehydrogenase which is encoded by gene mtlD. (EcoCyc) In E. coli, the transport of mannitol into the cell is done through a phosphotransferase system which attaches a phosphate to mannitol, producing mannitol 1-phosphate. (KEGG)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • D-Mannitol-1-phosphate
  • D-Mannitol-1-phosphoric acid
  • D-Mannitol-6-phosphate
  • D-Mannitol-6-phosphoric acid
  • Mannitol 1-phosphoric acid
  • Mannitol-1-P
  • Mannitol-1-phosphate
  • Mannitol-1-phosphoric acid
  • Mannitol-6-P
  • Mant1P
Chemical Formula:C6H15O9P
Weight:Average: 262.1517
Monoisotopic: 262.04536859
InChI Key:GACTWZZMVMUKNG-KVTDHHQDSA-N
InChI:InChI=1S/C6H15O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h3-11H,1-2H2,(H2,12,13,14)/t3-,4-,5-,6-/m1/s1
CAS number:15806-48-1
IUPAC Name:{[(2R,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]oxy}phosphonic acid
Traditional IUPAC Name:mannitol-1-phosphate
SMILES:OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=O
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
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility26.6 g/LALOGPS
logP-2.3ALOGPS
logP-3.9ChemAxon
logS-0.99ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area167.91 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity49.28 m³·mol⁻¹ChemAxon
Polarizability21.53 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Mannitol 1-phosphate + NAD > Fructose 6-phosphate + NADH
Mannitol 1-phosphate + NAD <> Fructose 6-phosphate + NADH + Hydrogen ion
Fructose 6-phosphate + NADH + Hydrogen ion + Fructose 6-phosphate <> NAD + Mannitol 1-phosphate
Mannitol + HPr - phosphorylated > Mannitol 1-phosphate + HPr
SMPDB Pathways:
glycolysis and pyruvate dehydrogenasePW000785 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Fructose and mannose metabolism ec00051
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006y-9540000000-86cf8d59afcce7584a3fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-0a4r-4923567000-26272b4c862b92140c1dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0w34-1490000000-d2e962eeeb8b5314f806View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9670000000-03053fb004aa1c4e49ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01q9-9300000000-4ba001d15034930de63bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-08i0-9300000000-9c3caddbe76982beb86cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0159-6900000000-eb42bdad711c5a7235ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-03di-0090000000-ae29abfa6b43be45ec2dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-03di-3090000000-4cd26f2bbad6c4388684View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-01r2-9050000000-ea7e8f0586758c6aba0dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, negativesplash10-002b-9010000000-93fe5d73664c635a907eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-002b-9000000000-e377d371c29e68aebaaaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 17V, negativesplash10-004j-9000000000-574c45306f876b8fb577View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 21V, negativesplash10-004i-9000000000-c903273e5dc08f87bedfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, negativesplash10-002b-9000000000-f8d2372dae0d91dd5c9bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-00di-0020090000-17eaa3895d63654aadfbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-03r0-0090090000-daad02df2a8857e3b044View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-03di-0090020000-51fd69100fe5fcfd7caaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-03di-0090000000-2b445bd7c879872a7e72View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, negativesplash10-03di-0090000000-7d28445e31e474a97c45View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 13V, negativesplash10-03di-0090000000-3fa243df5a46b4b1106dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-3690000000-bcc5097fd962872341bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03kc-9610000000-ac374a4fe18a51efbab7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03kd-9200000000-651b0e98592a21df2d7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-084v-9820000000-12be868166849360c049View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-7c23a52e0da63d89cc95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-0fa94fd955a1b1afa23aView in MoNA
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
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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 ID16298
HMDB IDHMDB01530
Pubchem Compound ID130418
Kegg IDC00644
ChemSpider ID115387
Wikipedia IDNot Available
BioCyc IDMANNITOL-1P
EcoCyc IDMANNITOL-1P

Enzymes

Protein Details
1. PTS system mannitol-specific EIICBA component
General function:
Involved in transporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in mannitol transport
Gene Name:
mtlA
Uniprot ID:
P00550
Molecular weight:
67972
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
Protein Details
2. Mannitol-1-phosphate 5-dehydrogenase
General function:
Involved in oxidation-reduction process
Specific function:
D-mannitol 1-phosphate + NAD(+) = D-fructose 6-phosphate + NADH
Gene Name:
mtlD
Uniprot ID:
P09424
Molecular weight:
41139
Reactions
D-mannitol 1-phosphate + NAD(+) = D-fructose 6-phosphate + NADH.
Protein Details
3. Mannitol-specific cryptic phosphotransferase enzyme IIA component
General function:
Involved in transporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in mannitol transport
Gene Name:
cmtB
Uniprot ID:
P69824
Molecular weight:
16046
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein Details
4. PTS system mannitol-specific cryptic EIICB component
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in mannitol transport
Gene Name:
cmtA
Uniprot ID:
P69826
Molecular weight:
48971
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.

Transporters

Protein Details
1. PTS system mannitol-specific EIICBA component
General function:
Involved in transporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in mannitol transport
Gene Name:
mtlA
Uniprot ID:
P00550
Molecular weight:
67972
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
Protein Details
2. PTS system mannitol-specific cryptic EIICB component
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in mannitol transport
Gene Name:
cmtA
Uniprot ID:
P69826
Molecular weight:
48971
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.