Myo-Inositol hexakisphosphate (YMDB00500)

Identification

YMDB ID

YMDB00500

Name

Myo-Inositol hexakisphosphate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

1D-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

MOL SDF PDB SMILES InChI

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 number

83-86-3

Weight

Average: 660.0353
Monoisotopic: 659.861370576

InChI Key

IMQLKJBTEOYOSI-GPIVLXJGSA-N

InChI

InChI=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 Name

phytic acid

Chemical Formula

C₆H₁₈O₂₄P₆

SMILES

OP(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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Inositol 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 Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Solid

Charge

Melting point

< 25 °C

Experimental Properties

Property	Value	Reference
Water Solubility	1000 mg/mL [MERCK INDEX (1996)]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	13.7 g/L	ALOGPS
logP	0.11	ALOGPS
logP	-4.5	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	0.14	ChemAxon
Physiological Charge	-12	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	400.56 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	101.01 m³·mol⁻¹	ChemAxon
Polarizability	42.71 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

nucleus
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Inositol Metabolism	PW002498
Inositol phosphate metabolism	PW002495

KEGG Pathways

Inositol phosphate metabolism

ec00562

SMPDB Reactions

KEGG Reactions

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9011130000-5431c0ee735538ced179	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-2000029000-170b59b987d1793da521	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-2000029000-2abfcb8b1f82e5ed9d0f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-5000910000-898702e2b03bf951e93b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-4000009000-9f6af14cfd403477a602	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000002000-e40f60df66da33ed1adc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-4637889507d0d883c7be	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	17401
HMDB ID	HMDB03502
Pubchem Compound ID	890
Kegg ID	C01204
ChemSpider ID	25060692
FOODB ID	FDB030293
Wikipedia	Phytic_acid
BioCyc ID	MI-HEXAKISPHOSPHATE

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. Diphosphoinositol polyphosphate phosphohydrolase DDP1

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.

Protein Details

3. Inositol hexakisphosphate kinase 1

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).

Protein Details

4. Inositol hexakisphosphate and diphosphoinositol-pentakisphosphate kinase

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).

Protein Details

5. Inositol-pentakisphosphate 2-kinase

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.

Structure for #<Compound:0xa6a0692c>

Enzymes

Reactions

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