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Identification
YMDB IDYMDB00946
NameInositol 1,3,4,5,6-pentakisphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description1D-Myo-Inositol 1,3,4,5,6-pentakisphosphate (IP5) is an intermediate in inositol pyrophosphates biosynthesis pathway. IP5 is the precursor 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
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
  • D-Myo-inositol 1,3,4,5,6-pentakisphosphoric acid
  • Inositol 1,3,4,5,6-pentakisphosphoric acid
  • alpha-D-Glucose 1,6-biphosphate
  • D-Glucose 1,6-biphosphate
  • D-Glucose 1,6-bisphosphate
  • a-D-Glucose 1,6-biphosphate
  • a-D-Glucose 1,6-biphosphoric acid
  • alpha-D-Glucose 1,6-biphosphoric acid
  • Α-D-glucose 1,6-biphosphate
  • Α-D-glucose 1,6-biphosphoric acid
  • D-Glucose 1,6-biphosphoric acid
  • D-Glucose 1,6-bisphosphoric acid
  • a-D-Glucose 1,6-bisphosphate
  • a-D-Glucose 1,6-bisphosphoric acid
  • alpha-D-Glucose 1,6-bisphosphoric acid
  • Α-D-glucose 1,6-bisphosphate
  • Α-D-glucose 1,6-bisphosphoric acid
  • a-D-Glucose 1,6-bis(dihydrogen phosphate)
  • a-D-Glucose 1,6-diphosphate
  • alpha-D-1,6-Bis(dihydrogen phosphate) glucopyranose
  • alpha-D-Glucose 1,6-bis(dihydrogen phosphate)
  • alpha-D-Glucose 1,6-diphosphate
  • alpha-delta-1,6-Bis(dihydrogen phosphate) glucopyranose
  • alpha-delta-Glucose 1,6-bis(dihydrogen phosphate)
  • alpha-delta-Glucose 1,6-bisphosphate
  • alpha-delta-Glucose 1,6-diphosphate
  • D-Glucose 1,6-diphosphate
  • delta-Glucose 1,6-diphosphate
  • Glucose 1,6-bisphosphate
  • Glucose 1,6-diphosphate
  • beta-D-Glucose 1,6-(bis)phosphate
  • Glucose-1,6-diphosphate
  • Glucose-1,6-bisphosphate
  • 1D-Myo-inositol 1,2,3,4,5,6-hexakisphosphate
  • 1D-Myo-inositol hexakisphosphate
  • Acide fytique
  • Acido fitico
  • Acidum fyticum
  • D-Myo-inositol 1,2,3,4,5,6-hexakisphosphate
  • Inosithexaphosphorsaeure
  • Myo-inositol 1,2,3,4,5,6-hexakisphosphate
  • Phytate
  • Phytic acid
  • Phytine
  • Saeure des phytins
  • Inositol 1,2,3,4,5,6-hexakisphosphate
  • 1D-Myo-inositol 1,2,3,4,5,6-hexakisphosphoric acid
  • 1D-Myo-inositol hexakisphosphoric acid
  • D-Myo-inositol 1,2,3,4,5,6-hexakisphosphoric acid
  • Myo-inositol 1,2,3,4,5,6-hexakisphosphoric acid
  • Inositol 1,2,3,4,5,6-hexakisphosphoric acid
  • Myo-inositol hexakisphosphoric acid
  • Inositol hexakis(phosphate)
  • Inositol hexaphosphate
  • Meso-inositol hexaphosphate
  • Myo-inositol hexakis(phosphate)
  • Myo-inositol hexaphosphate
  • 6-H2PO3glcbeta
  • 6-O-Phosphono-beta-D-glucopyranose
  • beta-D-Glucose 6-(dihydrogen phosphate)
  • beta-D-Glucose 6-phosphic acid
  • BETA-D-GLUCOSE-6-phosphATE
  • 6-O-Phosphono-b-D-glucopyranose
  • 6-O-Phosphono-β-D-glucopyranose
  • b-D-Glucose 6-(dihydrogen phosphate)
  • b-D-Glucose 6-(dihydrogen phosphoric acid)
  • beta-D-Glucose 6-(dihydrogen phosphoric acid)
  • Β-D-glucose 6-(dihydrogen phosphate)
  • Β-D-glucose 6-(dihydrogen phosphoric acid)
  • b-D-Glucose 6-phosphate
  • b-D-Glucose 6-phosphoric acid
  • beta-D-Glucose 6-phosphoric acid
  • Β-D-glucose 6-phosphate
  • Β-D-glucose 6-phosphoric acid
  • b-D-GLUCOSE-6-phosphate
  • b-D-GLUCOSE-6-phosphoric acid
  • beta-D-GLUCOSE-6-phosphoric acid
  • Β-D-glucose-6-phosphate
  • Β-D-glucose-6-phosphoric acid
  • [CO(OH)2]
  • Dihydrogen carbonate
  • H2CO3
  • Koehlensaeure
  • Dihydrogen carbonic acid
  • Hydrogen carbonic acid
  • Carbonate
  • Acid OF air
  • Aerial acid
  • Bisodium carbonate
  • Calcined
  • Carbonic acid sodium salt
  • Consal
  • Crystol carbonate
  • Disodium carbonate
  • Mild alkali
  • Na-X
  • Oxyper
  • Sal soda
  • Salt OF soda
  • Scotch soda
  • Soda
  • Soda ash
  • Sodium carbonate
  • Sodium carbonate anhydrous
  • Sodium carbonate hydrated
  • Sodium carbonate peroxyhydrate
  • Solvay soda
  • Trona soda ash
  • Tronalight light soda ash
  • Acid, carbonic
  • Carbonic acid
  • 3'-Adenosine monophosphate
  • 3'-Adenylic acid
  • Adenosine 3'-monophosphate
  • Adenosine 3'-phosphate
  • Adenosine-3'-monophosphate
  • AMP 3'-Phosphate
  • Synadenylic acid
  • 3'-Adenosine monophosphoric acid
  • 3'-Adenylate
  • Adenosine 3'-monophosphoric acid
  • Adenosine 3'-phosphoric acid
  • Adenosine-3'-monophosphoric acid
  • AMP 3'-Phosphoric acid
  • Synadenylate
  • Adenosine-3'-phosphate
  • Yeast adenylic acid
  • 2' Adenylic acid
  • 5' Adenylic acid
  • Phosphate dipotassium, adenosine
  • 5'-Adenylic acid
  • Adenylic acid
  • 5'-Phosphate, adenosine
  • Adenosine 2'-phosphate
  • Dipotassium, adenosine phosphate
  • Phosphate disodium, adenosine
  • monoPhosphate, 2'-adenosine
  • 2'-AMP
  • 2'-Adenosine monophosphate
  • Adenosine 2' phosphate
  • Adenosine phosphate dipotassium
  • Adenosine 3' phosphate
  • Disodium, adenosine phosphate
  • Phosphaden
  • 2'-Adenylic acid
  • AMP
  • Adenosine monophosphate
  • Adenosine phosphate disodium
  • 2' Adenosine monophosphate
  • Acid, 2'-adenylic
  • Acid, 5'-adenylic
  • Adenosine 5' phosphate
  • Adenosine 5'-phosphate
CAS number20298-95-7
WeightAverage: 580.0554
Monoisotopic: 579.895040166
InChI KeyCTPQAXVNYGZUAJ-KXXVROSKSA-N
InChIInChI=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{[(1S,2r,3R,4S,5r,6R)-2-hydroxy-3,4,5,6-tetrakis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional IUPAC Nameinositol pentaphosphate
Chemical FormulaC6H17O21P5
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.
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
LogP-7.999PhysProp
Predicted Properties
PropertyValueSource
Water Solubility13.4 g/LALOGPS
logP-0.14ALOGPS
logP-4.4ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)0.19ChemAxon
Physiological Charge-10ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area354.03 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity90.14 m³·mol⁻¹ChemAxon
Polarizability38.48 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
Inositol 1,3,4,5,6-pentakisphosphate + Adenosine triphosphateMyo-Inositol hexakisphosphate + ADP
Myo-Inositol hexakisphosphate + waterInositol 1,3,4,5,6-pentakisphosphate + phosphate
Inositol 1,3,4,5,6-pentakisphosphate + water1D-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 triphosphateInositol 1,3,4,5,6-pentakisphosphate + ADP
KEGG Reactions
5,6-Bis(diphospho)-1D-myo-inositol tetrakisphosphate + waterhydron + phosphate + Inositol 1,3,4,5,6-pentakisphosphate
Adenosine triphosphate + hydron + phosphate + Inositol 1,3,4,5,6-pentakisphosphatewater + ADP + 5,6-Bis(diphospho)-1D-myo-inositol tetrakisphosphate
Adenosine triphosphate + hydron + Inositol 1,3,4,5,6-pentakisphosphateMyo-Inositol hexakisphosphate + ADP
Adenosine triphosphate + hydron + 1D-Myo-Inositol 1,3,4,5-tetrakisphosphateADP + Inositol 1,3,4,5,6-pentakisphosphate
Adenosine triphosphate + hydron + 1D-Myo-inositol 1,4,5,6-tetrakisphosphateADP + Inositol 1,3,4,5,6-pentakisphosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-9022820000-0b347c8feac8081572f2JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udj-8421291000-e7a6038279ed0bab458bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-2000590000-a78e46f1069068bb0c1aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-1000390000-aeca364d94e2aaa6c4d6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-2019200000-69fb19c69da99cd9f2d2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-4000190000-e7d2cc4d7c8bcd94a4e4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000220000-c245a52aad69af0e69aeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-2809ce202dff18cc242cJSpectraViewer
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:
ResourceLink
CHEBI ID16322
HMDB IDHMDB03529
Pubchem Compound ID439468
Kegg IDC01284
ChemSpider ID23097113
FOODB IDFDB023187
WikipediaInositol_pentakisphosphate
BioCyc IDNot Available

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.