Identification
YMDB IDYMDB00852
Name1D-myo-inositol 1,4-bisphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-myo-Inositol 1,4-bisphosphate, also known as inositol 1,4-bisphosphoric acid, belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety. D-myo-Inositol 1,4-bisphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). D-myo-Inositol 1,4-bisphosphate exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
Synonyms
  • 1d-myo-inositol 1
  • 1D-myo-Inositol 1,4-bisphosphate
  • 1D-Myo-inositol 1,4-bisphosphic acid
  • 4-bisphosphate
  • D-myo-inositol 1,4-bisphosphate
  • D-MYO-INOSITOL-1,4-BISPHOSPHATE
  • inositol 1
  • inositol 1,4-bisphosphate
  • myo-inositol 1
  • myo-inositol 1,4-bisphosphate
  • D-MYO-inositol-1,4-bisphosphoric acid
  • Inositol 1,4-bisphosphoric acid
  • Myo-inositol 1,4-bisphosphoric acid
  • D-Myo-inositol 1,4-bisphosphoric acid
  • 1D-Myo-inositol 1,4-bisphosphoric acid
CAS number47055-78-7
WeightAverage: 340.1157
Monoisotopic: 339.996048936
InChI KeyPELZSPZCXGTUMR-RTPHHQFDSA-N
InChIInChI=1S/C6H14O12P2/c7-1-2(8)6(18-20(14,15)16)4(10)3(9)5(1)17-19(11,12)13/h1-10H,(H2,11,12,13)(H2,14,15,16)/t1-,2-,3-,4+,5+,6+/m1/s1
IUPAC Name{[(1R,2R,3R,4R,5R,6S)-2,3,5,6-tetrahydroxy-4-(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional IUPAC Name[(1R,2R,3R,4R,5R,6S)-2,3,5,6-tetrahydroxy-4-(phosphonooxy)cyclohexyl]oxyphosphonic acid
Chemical FormulaC6H14O12P2
SMILESO[C@H]1[C@@H](O)[C@@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1OP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentInositol phosphates
Alternative Parents
Substituents
  • Inositol phosphate
  • Monoalkyl phosphate
  • Cyclohexanol
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility24.4 g/LALOGPS
logP-1.3ALOGPS
logP-4ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)0.86ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area214.44 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.52 m³·mol⁻¹ChemAxon
Polarizability25.1 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Inositol MetabolismPW002498 ThumbThumb?image type=greyscaleThumb?image type=simple
Inositol phosphate metabolismPW002495 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Inositol phosphate metabolismec00562 Map00562
SMPDB Reactions
Inositol 1,4,5-trisphosphate + water1D-myo-inositol 1,4-bisphosphate + phosphate
1D-Myo-Inositol 1,3,4,5-tetrakisphosphate + water1D-myo-inositol 1,4-bisphosphate + phosphate
1D-myo-inositol 1,4-bisphosphate + waterD-Myo-inositol 4-phosphate + Phosphoric acid
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9321000000-9f623a36e7cbbf411892JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-03dj-9163026000-1848e4d3af73c15a6fe2JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2039000000-30867310a54aeefc9f07JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-2029000000-09a80b30252576945f03JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-8920000000-da85c9dd4243595988ccJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-4009000000-0bfc6eac93cb1d6f5150JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9012000000-52b4d66a2cc414f3c15fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-188d2aa04460c53bd120JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-409ec2d369e3f269fc61JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-9008000000-6a58e24bfb6d7b7533d3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f53a8156649b945c2aeeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-0c0a6b1789da56429e47JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0029000000-7b521123b7ad2af2e51cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9100000000-1e618537818490a76e76JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Whisstock, J. C., Romero, S., Gurung, R., Nandurkar, H., Ooms, L. M., Bottomley, S. P., Mitchell, C. A. (2000). "The inositol polyphosphate 5-phosphatases and the apurinic/apyrimidinic base excision repair endonucleases share a common mechanism for catalysis." J Biol Chem 275:37055-37061.10962003
  • Morales-Johansson, H., Jenoe, P., Cooke, F. T., Hall, M. N. (2004). "Negative regulation of phosphatidylinositol 4,5-bisphosphate levels by the INP51-associated proteins TAX4 and IRS4." J Biol Chem 279:39604-39610.15265867
Synthesis Reference:Auchus, Richard J.; Kaiser, Susan L.; Majerus, Philip W. Synthesis of inositol 1,2-(cyclic)-4,5-trisphosphate. Proceedings of the National Academy of Sciences of the United States of America (1987), 84(5), 1206-9.
External Links:
ResourceLink
CHEBI ID17816
HMDB IDHMDB00968
Pubchem Compound ID805
Kegg IDC01220
ChemSpider ID17216032
FOODB IDFDB022343
Wikipedia IDNot Available
BioCyc IDINOSITOL-1,4-BISPHOSPHATE

Enzymes

General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Controls the cellular levels and subcellular distribution of phosphatidylinositol 3-phosphate and phosphatidylinositol 4,5-bisphosphate. Plays an essential role in a TGN (trans Golgi network)-to-early endosome pathway. Involved in clathrin-mediated protein sorting at the TGN
Gene Name:
INP53
Uniprot ID:
Q12271
Molecular weight:
124576.0
Reactions
1-phosphatidyl-1D-myo-inositol 4,5-bisphosphate + H(2)O → 1-phosphatidyl-1D-myo-inositol 4-phosphate + phosphate.
D-myo-inositol 1,4,5-trisphosphate + H2O → D-myo-inositol 1,4-bisphosphate + phosphate
D-myo-inositol 1,3,4,5-tetrakisphosphate + H2O → D-myo-inositol 1,3,4-trisphosphate + phosphate
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Controls the cellular levels and subcellular distribution of phosphatidylinositol 3-phosphate and phosphatidylinositol 4,5-bisphosphate. Specifically functions within the early endocytic pathway and actin organization
Gene Name:
INP52
Uniprot ID:
P50942
Molecular weight:
133330.0
Reactions
1-phosphatidyl-1D-myo-inositol 4,5-bisphosphate + H(2)O → 1-phosphatidyl-1D-myo-inositol 4-phosphate + phosphate.
D-myo-inositol 1,4,5-trisphosphate + H2O → D-myo-inositol 1,4-bisphosphate + phosphate
D-myo-inositol 1,3,4,5-tetrakisphosphate + H2O → D-myo-inositol 1,3,4-trisphosphate + phosphate
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Controls the cellular levels and subcellular distribution of phosphatidylinositol 3-phosphate and phosphatidylinositol 4,5-bisphosphate. Plays an essential role in a TGN (trans Golgi network)-to-early endosome pathway. Involved in endocytosis and acts as a negative regulator of the Slm pathway which modulates polarized actin assembly and growth
Gene Name:
INP51
Uniprot ID:
P40559
Molecular weight:
108429.0
Reactions
1-phosphatidyl-1D-myo-inositol 4,5-bisphosphate + H(2)O → 1-phosphatidyl-1D-myo-inositol 4-phosphate + phosphate.