4,5-Bis(diphospho)-1D-myo-inositol tetrakisphosphate (YMDB00502)

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Identification

YMDB ID

YMDB00502

Name

4,5-Bis(diphospho)-1D-myo-inositol tetrakisphosphate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

4,5-Bis(diphospho)-1D-myo-inositol tetrakisphosphate 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. 4,5-Bis(diphospho)-1D-myo-inositol tetrakisphosphate is an extremely strong acidic compound (based on its pKa). 4,5-Bis(diphospho)-1D-myo-inositol tetrakisphosphate may be a unique S. cerevisiae (yeast) metabolite.

Structure

MOL SDF PDB SMILES InChI

Synonyms

4,5-Bis(diphospho)-1D-myo-inositol tetrakisphosphoric acid

CAS number

Not Available

Weight

Average: 819.9951
Monoisotopic: 819.794031396

InChI Key

GXPFHIDIIMSLOF-UZAAGFTCSA-N

InChI

InChI=1S/C6H20O30P8/c7-37(8,9)29-1-2(30-38(10,11)12)4(32-40(16,17)18)6(34-44(27,28)36-42(22,23)24)5(3(1)31-39(13,14)15)33-43(25,26)35-41(19,20)21/h1-6H,(H,25,26)(H,27,28)(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+/m0/s1

IUPAC Name

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

Traditional IUPAC Name

[(1R,2S,3R,4R,5S,6S)-3,4-di{[hydroxy(phosphonooxy)phosphoryl]oxy}-2,5,6-tris(phosphonooxy)cyclohexyl]oxyphosphonic acid

Chemical Formula

C₆H₂₀O₃₀P₈

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)OP(O)(O)=O)[C@H](OP(O)(=O)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
Organic pyrophosphate
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

1D-myo-inositol bis(diphosphate) tetrakisphosphate (CHEBI:53066 )

Physical Properties

State

Not Available

Charge

Melting point

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
Water Solubility	12.9 g/L	ALOGPS
logP	0.55	ALOGPS
logP	-5.4	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	0.14	ChemAxon
Physiological Charge	-13	ChemAxon
Hydrogen Acceptor Count	22	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	493.62 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	122.76 m³·mol⁻¹	ChemAxon
Polarizability	51.34 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

cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

phosphate + hydron + 4-Diphospho-1D-myo-inositol pentakisphosphate ↔ 4,5-Bis(diphospho)-1D-myo-inositol tetrakisphosphate + water

5-Diphosphoinositol pentakisphosphate + phosphate + hydron ↔ 4,5-Bis(diphospho)-1D-myo-inositol tetrakisphosphate + water

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 (TMS_1_8) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-2300004970-ced83d24ee7ebf6728fd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1100004910-a8a5b3d9099ec59f7ec6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006x-4300198200-9af96e295e6f5fcd3780	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-016r-4100000190-96155ec2cb529fa77cc8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9300001230-2a05f3cc062754a067b0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000010-144b88c8bfd557b7df36	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	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
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

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
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
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
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
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
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
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
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

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	53066
HMDB ID	Not Available
Pubchem Compound ID	44224022
Kegg ID	Not Available
ChemSpider ID	23107122
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. 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

2. 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).

4,5-Bis(diphospho)-1D-myo-inositol tetrakisphosphate (YMDB00502)

Structure for #<Compound:0xaef5e14c>

Enzymes

Reactions

Reactions