1D-Myo-Inositol 1,3,4,5-tetrakisphosphate (YMDB00711)

Identification
YMDB IDYMDB00711
Name1D-Myo-Inositol 1,3,4,5-tetrakisphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description1D-Myo-Inositol 1,3,4,5-tetrakisphosphate (IP4) is an intermediate in inositol pyrophosphates biosynthesis pathway. IP4 is the precursor to IP5 in 1D-myo-inositol hexakisphosphate (IP6) biosynthesis pathway. IP6 is one of the most prevalent forms of phosphorylated inositols in the eukaryotic cell. It is a strong chelator of important minerals such as calcium, magnesium, iron and zinc. The main function of IP6 in yeast is related to regulation of mRNA export from the nucleus. [Biocyc PWY-6369 and PWY-6361]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1,3,4,5-tetrakis(dihydrogen phosphate) myo-Inositol
  • 1D-myo-inositol 1,3,4,5-tetrakis(dihydrogen phosphate)
  • 1D-myo-Inositol 1,3,4,5-tetrakisphosphate
  • 1D-Myo-inositol 1,3,4,5-tetrakisphosphic acid
  • d-myo-inositol 1,3,4,5-tetrakisphosphate
  • Inositol 1,3,4,5-tetrakis(phosphate)
  • inositol 1,3,4,5-tetrakisphosphate
  • inositol-(1,3,4,5)-tetrakisphosphate
  • Inositol-1,3,4,5-tetrakisphosphate
  • Inositol-1,3,4,5-tetraphosphate
  • myo-Inositol 1,3,4,5-tetrakis(phosphate)
  • myo-Inositol 1,3,4,5-tetraphosphate
  • myo-Inositol-1,3,4,5-tetrakisphosphate
  • myo-Inositol, 1,3,4,5-tetrakis(dihydrogen phosphate)
  • D-Myo-inositol 1,3,4,5-tetrakisphosphoric acid
  • Inositol 1,3,4,5-tetrakisphosphoric acid
  • 1D-myo-Inositol 1,3,4,5-tetrakisphosphoric acid
  • D-myo-Inositol 1,3,4,5-tetrakis(phosphate)
  • IP4
  • Inositol 1,3,4,5-tetraphosphate
  • Ins(1,3,4,5)P(4)
  • Ins(1,3,4,5)P4
  • Ins-1,3,4,5-P4
CAS number102850-29-3
WeightAverage: 500.0755
Monoisotopic: 499.928709756
InChI KeyCIPFCGZLFXVXBG-CNWJWELYSA-N
InChIInChI=1S/C6H16O18P4/c7-1-3(21-25(9,10)11)2(8)5(23-27(15,16)17)6(24-28(18,19)20)4(1)22-26(12,13)14/h1-8H,(H2,9,10,11)(H2,12,13,14)(H2,15,16,17)(H2,18,19,20)/t1-,2-,3-,4+,5-,6-/m0/s1
IUPAC Name{[(1S,2S,3S,4S,5R,6S)-2,4-dihydroxy-3,5,6-tris(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional IUPAC Name[(1S,2S,3S,4S,5R,6S)-2,4-dihydroxy-3,5,6-tris(phosphonooxy)cyclohexyl]oxyphosphonic acid
Chemical FormulaC6H16O18P4
SMILESO[C@H]1[C@@H](OP(O)(O)=O)[C@H](O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=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
  • 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 Solubility11.5 g/LALOGPS
logP-0.45ALOGPS
logP-4.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)0.33ChemAxon
Physiological Charge-8ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area307.5 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity79.27 m³·mol⁻¹ChemAxon
Polarizability34.19 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 + water → Inositol 1,4,5-trisphosphate + phosphate
Inositol 1,3,4-trisphosphate + Adenosine triphosphate → 1D-Myo-Inositol 1,3,4,5-tetrakisphosphate + ADP
1D-Myo-Inositol 1,3,4,5-tetrakisphosphate + Adenosine triphosphate → Inositol 1,3,4,5,6-pentakisphosphate + ADP
Inositol 1,4,5-trisphosphate + Adenosine triphosphate → 1D-Myo-Inositol 1,3,4,5-tetrakisphosphate + ADP
1D-Myo-Inositol 1,3,4,5-tetrakisphosphate + water → Inositol 1,3,4-trisphosphate + phosphate
KEGG Reactions
Adenosine triphosphate + hydron + 1D-Myo-Inositol 1,3,4,5-tetrakisphosphate → ADP + Inositol 1,3,4,5,6-pentakisphosphate
Adenosine triphosphate + hydron + Inositol 1,4,5-trisphosphate → 1D-Myo-Inositol 1,3,4,5-tetrakisphosphate + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9033500000-40d3d4fb1dfc500ee207JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-3001950000-8bde1d0dcad1c609d6d4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-2001920000-c33b25f7e9af41d5d654JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-3129000000-f3f2e7fccb48b86bb61fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-3000900000-af9d7140e2bc712f10f3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9001400000-ab5da4d3f21cb6ec2131JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-d2897590cb37f5181545JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-43744c672ffce8e5f032JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-2000900000-6ab674f6f44d9a0c5209JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9001100000-64346515bbf245763135JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000090000-2a395f5fa8fd29e0fb49JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000590000-ed0820d6a0273f81a586JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ea-9125300000-590d6d9afcbefc5e29a8JSpectraViewer
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
  • 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
  • Xia, H. J., Yang, G. (2005). "Inositol 1,4,5-trisphosphate 3-kinases: functions and regulations." Cell Res 15:83-91.15740635
  • Pouillon, V., Hascakova-Bartova, R., Pajak, B., Adam, E., Bex, F., Dewaste, V., Van Lint, C., Leo, O., Erneux, C., Schurmans, S. (2003). "Inositol 1,3,4,5-tetrakisphosphate is essential for T lymphocyte development." Nat Immunol 4:1136-1143.14517551
  • 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
Synthesis Reference:DeSolms, S. Jane; Vacca, Joseph P.; Huff, Joel R. The total synthesis of (±)-myo-inositol-1,3,4-triphosphate, (±)-myo-inositol-2,4,5-triphosphate and (±)-myo-inositol-1,3,4,5-tetraphosphate. Tetrahedron Letters (1987), 28(39), 4503-6.
External Links:
ResourceLink
CHEBI ID16783
HMDB IDHMDB01059
Pubchem Compound ID107758
Kegg IDC01272
ChemSpider ID23097114
FOODB IDFDB022398
Wikipedia.
BioCyc IDCPD-506

Enzymes

Protein Details
1. Inositol polyphosphate multikinase
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.
Protein Details
2. Inositol-1,4,5-trisphosphate 5-phosphatase 1
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.