Record Information
Version2.0
Creation Date2012-05-31 14:09:53 -0600
Update Date2015-06-03 15:54:55 -0600
Secondary Accession Numbers
  • ECMDB06872
Identification
Name:D-Tagatose 1,6-bisphosphate
Description:D-Tagatose 1,6-bisphosphate is an intermediate in galactose metabolism.
Structure
Thumb
Synonyms:
  • 1,6-Di-O-phosphono-D-tagatofuranose
  • D-Tagatose 1,6-bisphosphate
  • D-Tagatose 1,6-bisphosphoric acid
  • Tagatose-1,6-diphosphate
  • Tagatose-1,6-diphosphoric acid
  • Tagatose1,6BP
Chemical Formula:C6H14O12P2
Weight:Average: 340.1157
Monoisotopic: 339.996048936
InChI Key:RNBGYGVWRKECFJ-OEXCPVAWSA-N
InChI:InChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4+,5+,6?/m1/s1
CAS number:Not Available
IUPAC Name:{[(3S,4R,5R)-2,3,4-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name:D-tagatose 1,6-bisphosphate
SMILES:O[C@@H]1[C@H](O)C(O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexose phosphates
Alternative Parents
Substituents
  • Hexose phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • C-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Tetrahydrofuran
  • 1,2-diol
  • Hemiacetal
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility16.1 g/LALOGPS
logP-1.5ALOGPS
logP-3ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)0.89ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.44 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity58.11 m³·mol⁻¹ChemAxon
Polarizability25.12 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Galactose metabolismPW000821 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01xt-9532000000-c3c4929a4987e34c0dc0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-003f-9461230000-19da9c5afe0fe39a52b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-6469000000-934f8ed1edcbd28bc667View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006y-7295000000-a5ca0806e65ba8c99e88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9700000000-02fcc2f4b95b801c5949View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-8509000000-2992f67772e061c3ffe5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-9ac5383c77bff5f6cb96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9d902dae0eabfe2165daView in MoNA
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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID4250
HMDB IDHMDB06872
Pubchem Compound ID6535
Kegg IDC03785
ChemSpider ID389117
Wikipedia IDNot Available
BioCyc IDTAGATOSE-1-6-DIPHOSPHATE
EcoCyc IDTAGATOSE-1-6-DIPHOSPHATE

Enzymes

General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
ATP + D-fructose 6-phosphate = ADP + D- fructose 1,6-bisphosphate
Gene Name:
pfkB
Uniprot ID:
P06999
Molecular weight:
32456
Reactions
ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate.
General function:
Involved in ATP binding
Specific function:
ATP + D-fructose 6-phosphate = ADP + D- fructose 1,6-bisphosphate
Gene Name:
pfkA
Uniprot ID:
P0A796
Molecular weight:
34842
Reactions
ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate.
General function:
Involved in catalytic activity
Specific function:
Catalytic subunit of the tagatose-1,6-bisphosphate aldolase kbaYZ, which catalyzes the reversible aldol condensation of dihydroxyacetone phosphate (DHAP or glycerone-phosphate) with glyceraldehyde 3-phosphate (G3P) to produce tagatose 1,6- bisphosphate (TBP). Requires kbaZ subunit for full activity and stability
Gene Name:
kbaY
Uniprot ID:
P0AB74
Molecular weight:
31293
Reactions
D-tagatose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate.
General function:
Involved in catalytic activity
Specific function:
Catalytic subunit of the tagatose-1,6-bisphosphate aldolase gatYZ, which catalyzes the reversible aldol condensation of dihydroxyacetone phosphate (DHAP or glycerone-phosphate) with glyceraldehyde 3-phosphate (G3P) to produce tagatose 1,6- bisphosphate (TBP). Requires gatZ subunit for full activity and stability. Is involved in the catabolism of galactitol
Gene Name:
gatY
Uniprot ID:
P0C8J6
Molecular weight:
30812
Reactions
D-tagatose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate.
General function:
Involved in catalytic activity
Specific function:
Component of the tagatose-1,6-bisphosphate aldolase gatYZ that is required for full activity and stability of the Y subunit. Could have a chaperone-like function for the proper and stable folding of gatY. When expressed alone, gatZ does not show any aldolase activity. Is involved in the catabolism of galactitol
Gene Name:
gatZ
Uniprot ID:
P0C8J8
Molecular weight:
47108
General function:
Involved in catalytic activity
Specific function:
Component of the tagatose-1,6-bisphosphate aldolase kbaYZ that is required for full activity and stability of the Y subunit. Could have a chaperone-like function for the proper and stable folding of kbaY. When expressed alone, kbaZ does not show any aldolase activity
Gene Name:
kbaZ
Uniprot ID:
P0C8K0
Molecular weight:
47192