You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB00500
NameMyo-Inositol hexakisphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description1D-Myo-Inositol 1,2,3,4,5,6-hexakisphosphate (phytic acid or IP6) is an intermediate in inositol pyrophosphates 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. In plant cells IP6 serves as a storage form of myo-inositol, phosphate and mineral nutrients for utilization during seed germination and seedling growth. [Biocyc PWY-6369 and PWY-6361]
Structure
Thumb
Synonyms
  • [2,3,4,5,6-pentakis(phosphonatooxy)cyclohexyl] phosphate
  • 1D-myo-Inositol 1,2,3,4,5,6-hexakisphosphate
  • 1D-myo-inositol hexakisphosphate
  • D-myo-Inositol 1,2,3,4,5,6-hexakisphosphate
  • Inositol 1,2,3,4,5,6-hexakisphosphate
  • myo-Inositol 1,2,3,4,5,6-hexakisphosphate
  • myo-Inositol hexakisphosphate
  • myo-Inositol hexakisphosphic acid
  • Phytate
  • Phytic acid
  • Myo-inositol hexakisphosphoric acid
  • Sodium phytate
  • Calcium phytate
  • Phytate, calcium
  • Acid, phytic
  • Hexakisphosphate, inositol
  • Inositol hexakisphosphate
  • Phytate, sodium
  • Phytin
  • Hexaphosphate, inositol
  • Inositol hexaphosphate
CAS number83-86-3
WeightAverage: 660.0353
Monoisotopic: 659.861370576
InChI KeyIMQLKJBTEOYOSI-GPIVLXJGSA-N
InChIInChI=1S/C6H18O24P6/c7-31(8,9)25-1-2(26-32(10,11)12)4(28-34(16,17)18)6(30-36(22,23)24)5(29-35(19,20)21)3(1)27-33(13,14)15/h1-6H,(H2,7,8,9)(H2,10,11,12)(H2,13,14,15)(H2,16,17,18)(H2,19,20,21)(H2,22,23,24)/t1-,2-,3-,4+,5-,6-
IUPAC Name{[2,3,4,5,6-pentakis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional IUPAC Namephytic acid
Chemical FormulaC6H18O24P6
SMILESOP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=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
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting point< 25 °C
Experimental Properties
PropertyValueReference
Water Solubility1000 mg/mL [MERCK INDEX (1996)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility13.7 g/LALOGPS
logP0.11ALOGPS
logP-4.5ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)0.14ChemAxon
Physiological Charge-12ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area400.56 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity101.01 m³·mol⁻¹ChemAxon
Polarizability42.71 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • nucleus
  • cytoplasm
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
5-Diphosphoinositol pentakisphosphate + water Myo-Inositol hexakisphosphate + phosphate
Myo-Inositol hexakisphosphate + Adenosine triphosphate5-Diphosphoinositol pentakisphosphate + ADP
Myo-Inositol hexakisphosphate + Adenosine triphosphate + hydron1-Diphosinositol pentakisphosphate + ADP
Myo-Inositol hexakisphosphate + Adenosine triphosphate + hydron5-Diphosphoinositol pentakisphosphate + ADP
Myo-Inositol hexakisphosphate + Adenosine triphosphate + hydron3-diphospho-1D-myo-inositol 1,2,4,5,6-pentakisphosphate + ADP
KEGG Reactions
water + 4-Diphospho-1D-myo-inositol pentakisphosphateMyo-Inositol hexakisphosphate + phosphate + hydron
5-Diphosphoinositol pentakisphosphate + waterMyo-Inositol hexakisphosphate + phosphate + hydron
Myo-Inositol hexakisphosphate + Adenosine triphosphate + hydron5-Diphosphoinositol pentakisphosphate + ADP
water + 6-Diphospho-1D-myo-inositol pentakisphosphateMyo-Inositol hexakisphosphate + phosphate + hydron
Adenosine triphosphate + hydron + Inositol 1,3,4,5,6-pentakisphosphateMyo-Inositol hexakisphosphate + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9011130000-5431c0ee735538ced179JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2000029000-170b59b987d1793da521JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2000029000-2abfcb8b1f82e5ed9d0fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5000910000-898702e2b03bf951e93bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-4000009000-9f6af14cfd403477a602JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000002000-e40f60df66da33ed1adcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4637889507d0d883c7beJSpectraViewer
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
  • Smolka, M. B., Albuquerque, C. P., Chen, S. H., Zhou, H. (2007). "Proteome-wide identification of in vivo targets of DNA damage checkpoint kinases." Proc Natl Acad Sci U S A 104:10364-10369.17563356
  • Mulugu, S., Bai, W., Fridy, P. C., Bastidas, R. J., Otto, J. C., Dollins, D. E., Haystead, T. A., Ribeiro, A. A., York, J. D. (2007). "A conserved family of enzymes that phosphorylate inositol hexakisphosphate." Science 316:106-109.17412958
  • 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
  • Lee, Y. S., Mulugu, S., York, J. D., O'Shea, E. K. (2007). "Regulation of a cyclin-CDK-CDK inhibitor complex by inositol pyrophosphates." Science 316:109-112.17412959
  • Gruhler, A., Olsen, J. V., Mohammed, S., Mortensen, P., Faergeman, N. J., Mann, M., Jensen, O. N. (2005). "Quantitative phosphoproteomics applied to the yeast pheromone signaling pathway." Mol Cell Proteomics 4:310-327.15665377
  • Albuquerque, C. P., Smolka, M. B., Payne, S. H., Bafna, V., Eng, J., Zhou, H. (2008). "A multidimensional chromatography technology for in-depth phosphoproteome analysis." Mol Cell Proteomics 7:1389-1396.18407956
  • Huh, W. K., Falvo, J. V., Gerke, L. C., Carroll, A. S., Howson, R. W., Weissman, J. S., O'Shea, E. K. (2003). "Global analysis of protein localization in budding yeast." Nature 425:686-691.14562095
  • Ives, E. B., Nichols, J., Wente, S. R., York, J. D. (2000). "Biochemical and functional characterization of inositol 1,3,4,5, 6-pentakisphosphate 2-kinases." J Biol Chem 275:36575-36583.10960485
  • Safrany, S. T., Ingram, S. W., Cartwright, J. L., Falck, J. R., McLennan, A. G., Barnes, L. D., Shears, S. B. (1999). "The diadenosine hexaphosphate hydrolases from Schizosaccharomyces pombe and Saccharomyces cerevisiae are homologues of the human diphosphoinositol polyphosphate phosphohydrolase. Overlapping substrate specificities in a MutT-type protein." J Biol Chem 274:21735-21740.10419486
  • Li, X., Gerber, S. A., Rudner, A. D., Beausoleil, S. A., Haas, W., Villen, J., Elias, J. E., Gygi, S. P. (2007). "Large-scale phosphorylation analysis of alpha-factor-arrested Saccharomyces cerevisiae." J Proteome Res 6:1190-1197.17330950
  • Miller, A. L., Suntharalingam, M., Johnson, S. L., Audhya, A., Emr, S. D., Wente, S. R. (2004). "Cytoplasmic inositol hexakisphosphate production is sufficient for mediating the Gle1-mRNA export pathway." J Biol Chem 279:51022-51032.15459192
Synthesis Reference:Mitsuhashi Naoto; Ohnishi Miwa; Sekiguchi Yoko; Kwon Yong-Uk; Chang Young-Tae; Chung Sung-Kee; Inoue Yoshinori; Reid Robert J; Yagisawa Hitoshi; Mimura Tetsuro Phytic acid synthesis and vacuolar accumulation in suspension-cultured cells of Catharanthus r
External Links:
ResourceLink
CHEBI ID17401
HMDB IDHMDB03502
Pubchem Compound ID890
Kegg IDC01204
ChemSpider ID25060692
FOODB IDFDB000374
WikipediaPhytic_acid
BioCyc IDMI-HEXAKISPHOSPHATE

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 hydrolase activity
Specific function:
May eliminate potentially toxic dinucleoside polyphosphates during sporulation. Most active against diadenosine 5',5'''-P1,P6-hexaphosphate (Ap6A). Can also hydrolyze diadenosine 5',5'''-P1,P5-pentaphosphate (Ap5A), adenosine 5'-pentaphosphate, and adenosine 5'-tetraphosphate are also substrates, but not diadenosine 5',5'''-P1,P4-tetraphosphate (Ap4A) or other dinucleotides, mononucleotides, nucleotide sugars, or nucleotide alcohols. Also cleaves a beta-phosphate from the diphosphate groups in PP-InsP5 (diphosphoinositol pentakisphosphate) and [PP]2-InsP4 (bisdiphosphoinositol tetrakisphosphate)
Gene Name:
DDP1
Uniprot ID:
Q99321
Molecular weight:
21572.30078
Reactions
Diphospho-myo-inositol polyphosphate + H(2)O → myo-inositol polyphosphate + phosphate.
General function:
Involved in inositol trisphosphate 3-kinase activity
Specific function:
Converts inositol hexakisphosphate (InsP6) to diphosphoinositol pentakisphosphate (InsP7/PP-InsP5). Involved in phosphate regulation and polyphosphate accumulation. Required for resistance to salt stress, cell wall integrity, vacuole morphogenesis, and telomere maintenance
Gene Name:
KCS1
Uniprot ID:
Q12494
Molecular weight:
119549.0
Reactions
ATP + 1D-myo-inositol hexakisphosphate → ADP + 5-diphospho-1D-myo-inositol (1,2,3,4,6)pentakisphosphate.
ATP + 1D-myo-inositol 1,3,4,5,6-pentakisphosphate → ADP + diphospho-1D-myo-inositol tetrakisphosphate (isomeric configuration unknown).
General function:
Involved in acid phosphatase activity
Specific function:
Bifunctional inositol kinase that catalyzes the formation of diphosphoinositol pentakisphosphate (InsP7 or PP- InsP5) and bi-diphosphoinositol tetrakisphosphate (InsP8 or PP2- InsP4). Converts inositolitol hexakisphosphate (InsP6) to InsP7. Also able to convert InsP7 to InsP8. Probably specifically mediates the formation of 4PP-InsP5 and 6PP-InsP5 InsP7 isomers but not of 5PP-IP5 InsP7 isomer. Required for maintaining celllular integrity, normal growth and interactions with the ARP complex. Acts as a regulator of the PHO80-PHO85 cyclin/cyclin-dependent kinase (CDK) complex, thereby regulating signaling of phosphate availability. Required for the function of the cortical actin cytoskeleton, possibly by participating in correct F-actin localization and ensuring polarized growth
Gene Name:
VIP1
Uniprot ID:
Q06685
Molecular weight:
129754.0
Reactions
ATP + 1D-myo-inositol hexakisphosphate → ADP + 5-diphospho-1D-myo-inositol (1,2,3,4,6)pentakisphosphate.
ATP + 1D-myo-inositol 1,3,4,5,6-pentakisphosphate → ADP + diphospho-1D-myo-inositol tetrakisphosphate (isomeric configuration unknown).
ATP + 1D-myo-inositol 5-diphosphate pentakisphosphate → ADP + 1D-myo-inositol bisdiphosphate tetrakisphosphate (isomeric configuration unknown).
General function:
Involved in ATP binding
Specific function:
Has kinase activity and phosphorylates inositol- 1,3,4,5,6-pentakisphosphate (Ins(1,3,4,5,6)P5) to produce 1,2,3,4,5,6-hexakisphosphate (InsP6), also known as phytate
Gene Name:
IPK1
Uniprot ID:
Q06667
Molecular weight:
32917.69922
Reactions
ATP + 1D-myo-inositol 1,3,4,5,6-pentakisphosphate → ADP + 1D-myo-inositol hexakisphosphate.