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Sorbitol-6-phosphate (M2MDB000371)

Record Information
Version2.0
Creation Date2012-05-31 13:51:45 -0600
Update Date2015-06-03 15:54:05 -0600
Secondary Accession Numbers
  • ECMDB01400
Identification
Name:Sorbitol-6-phosphate
DescriptionSorbitol 6-phosphate (Sor6P) is an intermediate in sorbitol biosynthesis. It is a competitive inhibitor for both cytosolic and chloroplastic PGIs with a K(i) of 61 and 40muM, respectively. PMID: 18242768
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • 1-O-Phosphono-D-glucitol
  • 1-O-Phosphono-D-mannitol
  • Alditol 6-phosphate
  • Alditol 6-phosphoric acid
  • D-Glucitol-6-phosphate
  • D-Glucitol-6-phosphoric acid
  • D-Mannitol 1-(dihydrogen phosphate)
  • D-Mannitol 1-(dihydrogen phosphoric acid)
  • D-Mannitol 1-phosphate
  • D-Mannitol 1-phosphoric acid
  • D-Mannitol, 1-(dihydrogenphosphate)
  • D-Mannitol, 1-(dihydrogenphosphoric acid)
  • D-Mannitol-6-phosphate
  • D-Mannitol-6-phosphoric acid
  • D-Sorbitol 6-phosphate
  • D-Sorbitol 6-phosphoric acid
  • Glucitol-6-phosphate
  • Glucitol-6-phosphoric acid
  • Sorbitol 6-phosphate
  • Sorbitol 6-phosphoric acid
  • Sorbitol-6-phosphate
  • Sorbitol-6-phosphoric acid
Chemical Formula:C6H15O9P
Weight:Average: 262.1517
Monoisotopic: 262.04536859
InChI Key:GACTWZZMVMUKNG-UHFFFAOYSA-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)
CAS number:20479-58-7
IUPAC Name:[(2,3,4,5,6-pentahydroxyhexyl)oxy]phosphonic acid
Traditional IUPAC Name:(2,3,4,5,6-pentahydroxyhexyl)oxyphosphonic acid
SMILES:OCC(O)C(O)C(O)C(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
Polarizability21.73 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Phosphoenolpyruvic acid + Sorbitol > Pyruvic acid + Sorbitol-6-phosphate
Phosphoenolpyruvic acid + Mannitol > Sorbitol-6-phosphate + Pyruvic acid
NAD + Sorbitol-6-phosphate <> Fructose 6-phosphate + Hydrogen ion + NADH
Sorbitol-6-phosphate + NAD <> beta-D-Fructose 6-phosphate + NADH + Hydrogen ion
Protein N(pi)-phospho-L-histidine + Mannitol <> Protein histidine + Sorbitol-6-phosphate
Protein N(pi)-phospho-L-histidine + Sorbitol <> Protein histidine + Sorbitol-6-phosphate
Phosphoenolpyruvic acid + Mannitol > Sorbitol-6-phosphate + Pyruvic acid
Phosphoenolpyruvic acid + Sorbitol > Sorbitol-6-phosphate + Pyruvic acid
Sorbitol-6-phosphate + NAD > Fructose 6-phosphate + NADH
Sorbitol-6-phosphate + HPr - phosphorylated > HPr
Sorbitol-6-phosphate + NAD <> beta-D-Fructose 6-phosphate + NADH + Hydrogen ion
SMPDB Pathways:
D-sorbitol degradation IIPW002022 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Fructose and mannose metabolism ec00051
  • Phosphotransferase system (PTS) ec02060
EcoCyc Pathways:
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
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-1490000000-12387329e9bd6200d625View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9100000000-750e7db58e5f275fa30dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-e36b916ac2d8b0b51b27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fv-9770000000-0cbecca1580218d23951View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-d1fa83df44a17d03f706View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-177256aadc387d9ad236View 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:
  • 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
  • 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
  • Zhou, R., Cheng, L. (2008). "Competitive inhibition of phosphoglucose isomerase of apple leaves by sorbitol 6-phosphate." J Plant Physiol 165:903-910. Pubmed: 18242768
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17044
HMDB IDHMDB05831
Pubchem Compound ID618
Kegg IDC02810
ChemSpider ID598
Wikipedia IDNot Available
BioCyc IDD-SORBITOL-6-P
EcoCyc IDD-SORBITOL-6-P

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. Glucitol/sorbitol-specific phosphotransferase enzyme IIA component
General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase 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 glucitol/sorbitol transport
Gene Name:
srlB
Uniprot ID:
P05706
Molecular weight:
13304
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein Details
3. Sorbitol-6-phosphate 2-dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
D-sorbitol 6-phosphate + NAD(+) = D-fructose 6-phosphate + NADH
Gene Name:
srlD
Uniprot ID:
P05707
Molecular weight:
27858
Reactions
D-sorbitol 6-phosphate + NAD(+) = D-fructose 6-phosphate + NADH.
Protein Details
4. Phosphoenolpyruvate-protein phosphotransferase
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. Enzyme I transfers the phosphoryl group from phosphoenolpyruvate (PEP) to the phosphoryl carrier protein (HPr)
Gene Name:
ptsI
Uniprot ID:
P08839
Molecular weight:
63561
Reactions
Phosphoenolpyruvate + protein L-histidine = pyruvate + protein N(pi)-phospho-L-histidine.
Protein Details
5. 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
6. Glucitol/sorbitol-specific phosphotransferase enzyme IIB component
General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase 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 glucitol/sorbitol transport
Gene Name:
srlE
Uniprot ID:
P56580
Molecular weight:
33332
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
Protein Details
7. PTS system mannose-specific EIIAB component
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
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 mannose transport
Gene Name:
manX
Uniprot ID:
P69797
Molecular weight:
35047
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
8. 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
9. 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.
Protein Details
10. Glucitol/sorbitol permease IIC component
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in glucitol/sorbitol transport
Gene Name:
srlA
Uniprot ID:
P56579
Molecular weight:
20580
Protein Details
11. Mannose permease IIC component
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manY
Uniprot ID:
P69801
Molecular weight:
27636
Protein Details
12. Mannose permease IID component
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manZ
Uniprot ID:
P69805
Molecular weight:
31303
Protein Details
13. Phosphocarrier protein HPr
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. The phosphoryl group from phosphoenolpyruvate (PEP) is transferred to the phosphoryl carrier protein HPr by enzyme I. Phospho-HPr then transfers it to the permease (enzymes II/III)
Gene Name:
ptsH
Uniprot ID:
P0AA04
Molecular weight:
9119
Reactions
Protein HPr N(pi)-phospho-L-histidine + protein EIIA = protein HPr + protein EIIA N(tau)-phospho-L-histidine.

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.
Protein Details
3. Glucitol/sorbitol permease IIC component
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in glucitol/sorbitol transport
Gene Name:
srlA
Uniprot ID:
P56579
Molecular weight:
20580
Protein Details
4. Mannose permease IIC component
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manY
Uniprot ID:
P69801
Molecular weight:
27636
Protein Details
5. Mannose permease IID component
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manZ
Uniprot ID:
P69805
Molecular weight:
31303