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Identification
YMDB IDYMDB00291
NameInositol 1,4,5-trisphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionInositol 1,4,5-trisphosphate, also known as 1,4,5-insp3 or IP3, 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. Inositol 1,4,5-trisphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Inositol 1,4,5-trisphosphate exists in all eukaryotes, ranging from yeast to humans. Within yeast, inositol 1,4,5-trisphosphate participates in a number of enzymatic reactions. In particular, inositol 1,4,5-trisphosphate can be converted into 1D-myo-inositol 1,4,5,6-tetrakisphosphate; which is catalyzed by the enzyme inositol polyphosphate multikinase. In addition, inositol 1,4,5-trisphosphate can be converted into 1D-myo-inositol 1,4-bisphosphate; which is mediated by the enzyme phosphatidylinositol 4,5-bisphosphate 5-phosphatase a. In yeast, inositol 1,4,5-trisphosphate is involved in the metabolic pathway called the inositol phosphate metabolism pathway.
Structure
Thumb
Synonyms
  • 1D-myo-Inositol 1,4,5-trisphosphate
  • D-myo-Inositol 1,4,5-trisphosphate
  • Inositol 1,4,5-trisphosphate
  • Inositol 1,4,5-trisphosphic acid
  • 1,4,5-Insp3
  • D-MYO-inositol-1,4,5-triphosphATE
  • Ins(1,4,5)P3
  • InsP3
  • IP3
  • D-Myo-inositol 1,4,5-trisphosphoric acid
  • D-MYO-inositol-1,4,5-triphosphoric acid
  • 1D-Myo-inositol 1,4,5-trisphosphoric acid
  • Inositol 1,4,5-trisphosphoric acid
  • Myo-inositol 1,4,5-trisphosphate
  • 1,4,5-IP3
  • Inositol 1,4,5-triphosphate
  • Myoinositol 1,4,5-triphosphate
CAS number88269-39-0
WeightAverage: 420.0956
Monoisotopic: 419.962379346
InChI KeyMMWCIQZXVOZEGG-XJTPDSDZSA-N
InChIInChI=1S/C6H15O15P3/c7-1-2(8)5(20-23(13,14)15)6(21-24(16,17)18)3(9)4(1)19-22(10,11)12/h1-9H,(H2,10,11,12)(H2,13,14,15)(H2,16,17,18)/t1-,2+,3+,4-,5-,6-/m1/s1
IUPAC Name{[(1R,2S,3R,4R,5S,6R)-2,3,5-trihydroxy-4,6-bis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional IUPAC NameInsP3
Chemical FormulaC6H15O15P3
SMILES[H]O[C@]1([H])[C@]([H])(O[H])[C@@]([H])(OP(=O)(O[H])O[H])[C@]([H])(OP(=O)(O[H])O[H])[C@@]([H])(O[H])[C@]1([H])OP(=O)(O[H])O[H]
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility14.8 g/LALOGPS
logP-0.86ALOGPS
logP-4.2ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)0.54ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-6ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area260.97 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity68.39 m³·mol⁻¹ChemAxon
Polarizability29.64 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • nucleus
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
1D-Myo-Inositol 1,3,4,5-tetrakisphosphate + waterInositol 1,4,5-trisphosphate + phosphate
Inositol 1,4,5-trisphosphate + Adenosine triphosphate1D-Myo-Inositol 1,3,4,5-tetrakisphosphate + ADP
Adenosine triphosphate + Inositol 1,4,5-trisphosphateADP + 1D-Myo-inositol 1,4,5,6-tetrakisphosphate
Inositol 1,4,5-trisphosphate + water1D-myo-inositol 1,4-bisphosphate + phosphate
Inositol 1,4,5-trisphosphate + Adenosine triphosphate1D-Myo-Inositol 1,3,4,5-tetrakisphosphate + ADP
KEGG Reactions
Adenosine triphosphate + hydron + Inositol 1,4,5-trisphosphate1D-Myo-inositol 1,4,5,6-tetrakisphosphate + ADP
Adenosine triphosphate + hydron + Inositol 1,4,5-trisphosphate1D-Myo-Inositol 1,3,4,5-tetrakisphosphate + ADP
water + 1D-myo-inositol 4,5-bisphosphateDG(16:0/16:0/0:0) + Inositol 1,4,5-trisphosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002b-7195200000-2871156f7c1e00704088JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0002-9052133000-5094b6ef55759c5a19ddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-3008900000-e987cfb2603d94f1a6a4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-2006900000-95047338604f8928313fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-4291000000-8e9bb388f01ec6d535abJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-4001900000-395b5e207aa26dd43f27JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9003200000-5e6369906fdedd08ad60JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4b72b937fe3bf7fe817eJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Dubois, E., Scherens, B., Vierendeels, F., Ho, M. M., Messenguy, F., Shears, S. B. (2002). "In Saccharomyces cerevisiae, the inositol polyphosphate kinase activity of Kcs1p is required for resistance to salt stress, cell wall integrity, and vacuolar morphogenesis." J Biol Chem 277:23755-23763.11956213
  • Flick, J. S., Thorner, J. (1993). "Genetic and biochemical characterization of a phosphatidylinositol-specific phospholipase C in Saccharomyces cerevisiae." Mol Cell Biol 13:5861-5876.8395015
Synthesis Reference:Cooke, Allan M.; Potter, Barry V. L.; Gigg, Roy. Synthesis of DL-myo-inositol 1,4,5-trisphosphate. Tetrahedron Letters (1987), 28(20), 2305-8.
External Links:
ResourceLink
CHEBI ID16595
HMDB IDHMDB01498
Pubchem Compound ID439456
Kegg IDC01245
ChemSpider ID23097104
FOODB IDFDB022657
WikipediaInositol 1,4,5-trisphosphate
BioCyc IDinositol_1,4,5-trisphosphate

Enzymes

General function:
Involved in inositol trisphosphate 3-kinase activity
Specific function:
Has kinase activity and phosphorylates inositol-1,4,5- trisphosphate (Ins(1,4,5)P3) and inositol-1,3,4,5- tetrakisphosphate (Ins(1,3,4,5)P4). Has low kinase activity towards InsP6. Originally it was proposed that the ARGRI and ARGRIII proteins are more likely to be involved in the control of ARGRII activity
Gene Name:
ARG82
Uniprot ID:
P07250
Molecular weight:
40352.5
Reactions
ATP + 1D-myo-inositol 1,4,5-trisphosphate → ADP + 1D-myo-inositol 1,4,5,6-tetrakisphosphate.
ATP + 1D-myo-inositol 1,4,5,6-tetrakisphosphate → ADP + 1D-myo-inositol 1,3,4,5,6-pentakisphosphate.
General function:
Involved in protein binding
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes. Required for cell growth, osmoresistance and expression of GPD1
Gene Name:
PLC1
Uniprot ID:
P32383
Molecular weight:
100547.0
Reactions
1-phosphatidyl-1D-myo-inositol 4,5-bisphosphate + H(2)O → 1D-myo-inositol 1,4,5-trisphosphate + diacylglycerol.
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.