Inositol 1,3,4,5,6-pentakisphosphate (YMDB00946)

Identification

YMDB ID

YMDB00946

Name

Inositol 1,3,4,5,6-pentakisphosphate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Inositol 1,3,4,5,6-pentakisphosphate, also known as inositol pentaphosphate, 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 1,3,4,5,6-pentakisphosphate is an extremely strong acidic compound (based on its pKa). Inositol 1,3,4,5,6-pentakisphosphate exists in all living species, ranging from bacteria to humans. Within yeast, inositol 1,3,4,5,6-pentakisphosphate participates in a number of enzymatic reactions. In particular, inositol 1,3,4,5,6-pentakisphosphate can be converted into myo-inositol hexakisphosphate through its interaction with the enzyme inositol-pentakisphosphate 2-kinase. In addition, inositol 1,3,4,5,6-pentakisphosphate can be biosynthesized from myo-inositol hexakisphosphate; which is mediated by the enzyme multiple inositol polyphosphate phosphatase 1. In yeast, inositol 1,3,4,5,6-pentakisphosphate is involved in the metabolic pathway called the inositol phosphate metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

1D-myo-Inositol 1,3,4,5,6-pentakisphosphate
Inositol 1,3,4,5,6-pentaphosphate
Inositol pentaphosphate
myo-Inositol 1,3,4,5,6-pentakis(phosphate)
myo-Inositol 1,3,4,5,6-pentaphosphate
myo-inositol pentakisphosphate
D-myo-Inositol 1,3,4,5,6-pentakisphosphate
1D-myo-Inositol 1,3,4,5,6-pentakisphosphoric acid
Inositol 1,3,4,5,6-pentakisphosphoric acid
D-myo-Inositol 1,3,4,5,6-pentakisphosphoric acid
I(1,3,4,5,6)P5
Inositol 1,3,4,5,6-pentakisphosphate
Ins(1,3,4,5,6)P5
myo-inositol 1,3,4,5,6-pentakisphosphate

CAS number

20298-95-7

Weight

Average: 580.0554
Monoisotopic: 579.895040166

InChI Key

CTPQAXVNYGZUAJ-KXXVROSKSA-N

InChI

InChI=1S/C6H17O21P5/c7-1-2(23-28(8,9)10)4(25-30(14,15)16)6(27-32(20,21)22)5(26-31(17,18)19)3(1)24-29(11,12)13/h1-7H,(H2,8,9,10)(H2,11,12,13)(H2,14,15,16)(H2,17,18,19)(H2,20,21,22)/t1-,2+,3-,4-,5+,6+

IUPAC Name

{[(1R,2S,3r,4R,5S,6r)-3-hydroxy-2,4,5,6-tetrakis(phosphonooxy)cyclohexyl]oxy}phosphonic acid

Traditional IUPAC Name

[(1R,2S,3r,4R,5S,6r)-3-hydroxy-2,4,5,6-tetrakis(phosphonooxy)cyclohexyl]oxyphosphonic acid

Chemical Formula

C₆H₁₇O₂₁P₅

SMILES

[H]O[C@]1([H])[C@]([H])(OP(=O)(O[H])O[H])[C@@]([H])(OP(=O)(O[H])O[H])[C@]([H])(OP(=O)(O[H])O[H])[C@@]([H])(OP(=O)(O[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.

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
Cyclohexanol
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Secondary alcohol
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

myo-inositol pentakisphosphate (CHEBI:16322 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	-7.999	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	13.4 g/L	ALOGPS
logP	-0.14	ALOGPS
logP	-4.4	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	0.19	ChemAxon
Physiological Charge	-10	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	354.03 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	90.14 m³·mol⁻¹	ChemAxon
Polarizability	38.48 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

Inositol 1,3,4,5,6-pentakisphosphate + Adenosine triphosphate → Myo-Inositol hexakisphosphate + ADP

Myo-Inositol hexakisphosphate + water → Inositol 1,3,4,5,6-pentakisphosphate + phosphate

Inositol 1,3,4,5,6-pentakisphosphate + water → 1D-Myo-inositol 1,4,5,6-tetrakisphosphate + phosphate

Inositol 1,3,4,5,6-pentakisphosphate + ADP → D-Myo-inositol 3,4,5,6-tetrakisphosphate + Adenosine triphosphate

1D-Myo-Inositol 1,3,4,5-tetrakisphosphate + Adenosine triphosphate → Inositol 1,3,4,5,6-pentakisphosphate + ADP

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	splash10-000t-9022820000-0b347c8feac8081572f2	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0udj-8421291000-e7a6038279ed0bab458b	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("myo-Inositol 1,3,4,5,6-pentakisphosphate,1TMS,#1" TMS) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_5) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_6) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - n/a 40V, negative	splash10-0udi-1000900000-189387da7b3691739738	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 40V, negative	splash10-001i-0009000000-d8e4bd96982581664cb8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 40V, negative	splash10-06si-0976000000-4348a6ca785e225be82b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 40V, negative	splash10-0udi-0000900000-73573d716178b0ffb8dd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 40V, negative	splash10-0udi-0109000000-21271275bbff7f497e41	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 40V, negative	splash10-08gi-0977000000-4950d48887941a016c30	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 40V, negative	splash10-004i-9000000000-46d4cee1b5ac630ba9b8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 40V, negative	splash10-052r-0900000000-4df79b7aad7183429c3e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 40V, negative	splash10-0a4i-0941000000-ebf11ba55edea9d0d03c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 40V, negative	splash10-0udi-0109000000-4701557ed0d5f78bceee	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 40V, negative	splash10-0a4i-0970000000-64206d567dce176ff875	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 40V, negative	splash10-001i-0009200000-ddb1fa1c37d0ac5a6c75	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 40V, negative	splash10-06ri-0977000000-778f76090718afa48252	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 23V, negative	splash10-004i-0000090000-09b887f4588457992521	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 26V, negative	splash10-004i-0000290000-99907810b58601057eb2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 30V, negative	splash10-0059-0000890000-1db30e238cc14e69ef7c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 32V, negative	splash10-003r-0000940000-cdf319ca2ef7756b6fa2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 39V, negative	splash10-001i-0102900000-2a426dc0f4578da92fc2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 49V, negative	splash10-0kcr-0816900000-c79cbf49bffaaf498cbe	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-2000590000-a78e46f1069068bb0c1a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-1000390000-aeca364d94e2aaa6c4d6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-2019200000-69fb19c69da99cd9f2d2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-4000190000-e7d2cc4d7c8bcd94a4e4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000220000-c245a52aad69af0e69ae	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-2809ce202dff18cc242c	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
Saiardi, A., Caffrey, J. J., Snyder, S. H., Shears, S. B. (2000). "Inositol polyphosphate multikinase (ArgRIII) determines nuclear mRNA export in Saccharomyces cerevisiae." FEBS Lett 468:28-32.10683435
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
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:

Not Available

External Links:

Resource	Link
CHEBI ID	16322
HMDB ID	HMDB03529
Pubchem Compound ID	439468
Kegg ID	C01284
ChemSpider ID	23097113
FOODB ID	FDB023187
Wikipedia	Inositol_pentakisphosphate
BioCyc ID	Not Available

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.

Inositol 1,3,4,5,6-pentakisphosphate (YMDB00946)

Structure for #<Compound:0xad210e3c>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions