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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-12 23:08:41 UTC
Update Date2020-05-15 16:43:08 UTC
HMDB IDHMDB0003529
Secondary Accession Numbers
  • HMDB0006232
  • HMDB03529
  • HMDB06232
Metabolite Identification
Common Namemyo-Inositol 1,3,4,5,6-pentakisphosphate
Descriptionmyo-Inositol 1,3,4,5,6-pentakisphosphate, also known as Ins(1,3,4,5,6)P5 or inositol pentaphosphate, is an inositol polyphosphate of emerging significance in cellular signalling. Both Ins(1,3,4,5,6)P5 and its C-2 epimer scyllo-inositol pentakisphosphate (scyllo-InsP(5)) were synthesized from the same myo-inositol-based precursor (PMID: 16755629 ). InsP6, Ins(1,3,4,5,6)P5, and their close metabolic relatives are amongst the more abundant intracellular inositol polyphosphates. They are involved in chromatin organization, DNA maintenance, gene transcription, nuclear mRNA transport, membrane trafficking, and control of cell proliferation (PMID: 14992690 ).
Structure
Data?1589560988
Synonyms
ValueSource
1D-myo-Inositol 1,3,4,5,6-pentakisphosphateChEBI
D-myo-Inositol 1,3,4,5,6-pentakisphosphateChEBI
1D-myo-Inositol 1,3,4,5,6-pentakisphosphoric acidGenerator
Inositol 1,3,4,5,6-pentakisphosphoric acidGenerator
D-myo-Inositol 1,3,4,5,6-pentakisphosphoric acidGenerator
Inositol 1,3,4,5,6-pentaphosphateHMDB
Inositol pentaphosphateHMDB
myo-Inositol 1,3,4,5,6-pentakis(phosphate)HMDB
myo-Inositol 1,3,4,5,6-pentaphosphateHMDB
myo-Inositol pentakisphosphateHMDB
I(1,3,4,5,6)P5HMDB
Inositol 1,3,4,5,6-pentakisphosphateHMDB
Ins(1,3,4,5,6)P5HMDB
myo-inositol 1,3,4,5,6-pentakisphosphateHMDB
Chemical FormulaC6H17O21P5
Average Molecular Weight580.0554
Monoisotopic Molecular Weight579.895040166
IUPAC Name{[(1R,2S,3r,4R,5S,6r)-3-hydroxy-2,4,5,6-tetrakis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional Name[(1R,2S,3r,4R,5S,6r)-3-hydroxy-2,4,5,6-tetrakis(phosphonooxy)cyclohexyl]oxyphosphonic acid
CAS Registry Number20298-95-7
SMILES
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
InChI Identifier
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+
InChI KeyCTPQAXVNYGZUAJ-KXXVROSKSA-N
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
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-7.999Not Available
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-9022820000-0b347c8feac8081572f2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udj-8421291000-e7a6038279ed0bab458bSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 40V, negativesplash10-0udi-1000900000-189387da7b3691739738Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 40V, negativesplash10-001i-0009000000-d8e4bd96982581664cb8Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 40V, negativesplash10-06si-0976000000-4348a6ca785e225be82bSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 40V, negativesplash10-0udi-0000900000-73573d716178b0ffb8ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 40V, negativesplash10-0udi-0109000000-21271275bbff7f497e41Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 40V, negativesplash10-08gi-0977000000-4950d48887941a016c30Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 40V, negativesplash10-004i-9000000000-46d4cee1b5ac630ba9b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 40V, negativesplash10-052r-0900000000-4df79b7aad7183429c3eSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 40V, negativesplash10-0a4i-0941000000-ebf11ba55edea9d0d03cSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 40V, negativesplash10-0udi-0109000000-4701557ed0d5f78bceeeSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 40V, negativesplash10-0a4i-0970000000-64206d567dce176ff875Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 40V, negativesplash10-001i-0009200000-ddb1fa1c37d0ac5a6c75Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 40V, negativesplash10-06ri-0977000000-778f76090718afa48252Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 23V, negativesplash10-004i-0000090000-09b887f4588457992521Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 26V, negativesplash10-004i-0000290000-99907810b58601057eb2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, negativesplash10-0059-0000890000-1db30e238cc14e69ef7cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 32V, negativesplash10-003r-0000940000-cdf319ca2ef7756b6fa2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 39V, negativesplash10-001i-0102900000-2a426dc0f4578da92fc2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 49V, negativesplash10-0kcr-0816900000-c79cbf49bffaaf498cbeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-2000590000-a78e46f1069068bb0c1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-1000390000-aeca364d94e2aaa6c4d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-2019200000-69fb19c69da99cd9f2d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-4000190000-e7d2cc4d7c8bcd94a4e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000220000-c245a52aad69af0e69aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-2809ce202dff18cc242cSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Nucleus
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023187
KNApSAcK IDNot Available
Chemspider ID10333900
KEGG Compound IDC01284
BioCyc IDCPD-1107
BiGG ID37275
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID16322
Food Biomarker OntologyNot Available
VMH IDMI13456P
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Riley AM, Trusselle M, Kuad P, Borkovec M, Cho J, Choi JH, Qian X, Shears SB, Spiess B, Potter BV: scyllo-inositol pentakisphosphate as an analogue of myo-inositol 1,3,4,5,6-pentakisphosphate: chemical synthesis, physicochemistry and biological applications. Chembiochem. 2006 Jul;7(7):1114-22. [PubMed:16755629 ]
  2. Barker CJ, Wright J, Hughes PJ, Kirk CJ, Michell RH: Complex changes in cellular inositol phosphate complement accompany transit through the cell cycle. Biochem J. 2004 Jun 1;380(Pt 2):465-73. [PubMed:14992690 ]

Enzymes

General function:
Involved in inositol trisphosphate 3-kinase activity
Specific function:
Inositol phosphate kinase with a broad substrate specificity. Has a preference for inositol 1,4,5-trisphosphate (Ins(1,4,5)P3) and inositol 1,3,4,6-tetrakisphosphate (Ins(1,3,4,6)P4).
Gene Name:
IPMK
Uniprot ID:
Q8NFU5
Molecular weight:
47221.455
Reactions
Adenosine triphosphate + D-myo-Inositol 1,4,5,6-tetrakisphosphate → ADP + myo-Inositol 1,3,4,5,6-pentakisphosphatedetails
Adenosine triphosphate + myo-Inositol 1,4,5-trisphosphate → ADP + myo-Inositol 1,3,4,5,6-pentakisphosphatedetails
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Acts as a modulator of macrophage activation through control of glucose metabolism (By similarity).
Gene Name:
SHPK
Uniprot ID:
Q9UHJ6
Molecular weight:
51504.425
General function:
Involved in catalytic activity
Specific function:
Kinase that can phosphorylate various inositol polyphosphate such as Ins(3,4,5,6)P4 or Ins(1,3,4)P3. Phosphorylates Ins(3,4,5,6)P4 at position 1 to form Ins(1,3,4,5,6)P5. This reaction is thought to have regulatory importance, since Ins(3,4,5,6)P4 is an inhibitor of plasma membrane Ca(2+)-activated Cl(-) channels, while Ins(1,3,4,5,6)P5 is not. Also phosphorylates Ins(1,3,4)P3 on O-5 and O-6 to form Ins(1,3,4,6)P4, an essential molecule in the hexakisphosphate (InsP6) pathway. Also acts as an inositol polyphosphate phosphatase that dephosphorylate Ins(1,3,4,5)P4 and Ins(1,3,4,6)P4 to Ins(1,3,4)P3, and Ins(1,3,4,5,6)P5 to Ins(3,4,5,6)P4. May also act as an isomerase that interconverts the inositol tetrakisphosphate isomers Ins(1,3,4,5)P4 and Ins(1,3,4,6)P4 in the presence of ADP and magnesium. Probably acts as the rate-limiting enzyme of the InsP6 pathway. Modifies TNF-alpha-induced apoptosis by interfering with the activation of TNFRSF1A-associated death domain.
Gene Name:
ITPK1
Uniprot ID:
Q13572
Molecular weight:
45620.645
Reactions
Adenosine triphosphate + D-myo-Inositol 3,4,5,6-tetrakisphosphate → ADP + myo-Inositol 1,3,4,5,6-pentakisphosphatedetails
General function:
Involved in ATP binding
Specific function:
Phosphorylates Ins(1,3,4,5,6)P5 at position 2 to form Ins(1,2,3,4,5,6)P6 (InsP6 or phytate). InsP6 is involved in many processes such as mRNA export, non-homologous end-joining, endocytosis, ion channel regulation. It also protects cells from TNF-alpha-induced apoptosis.
Gene Name:
IPPK
Uniprot ID:
Q9H8X2
Molecular weight:
56016.12
Reactions
myo-Inositol hexakisphosphate + ADP → myo-Inositol 1,3,4,5,6-pentakisphosphate + Adenosine triphosphatedetails