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Record Information
Version3.6
Creation Date2006-08-12 23:08:41 UTC
Update Date2016-02-11 01:06:21 UTC
HMDB IDHMDB03529
Secondary Accession Numbers
  • HMDB06232
Metabolite Identification
Common NameInositol 1,3,4,5,6-pentakisphosphate
Descriptionmyo-Inositol 1,3,4,5,6-pentakisphosphate (Ins(1,3,4,5,6)P(5)), an inositol polyphosphate of emerging significance in cellular signalling, and its C-2 epimer scyllo-inositol pentakisphosphate (scyllo-InsP(5)) were synthesised from the same myo-inositol-based precursor. (PMID: 16755629 ). InsP6, Ins(1,3,4,5,6)P5 and their close metabolic relatives, which are amongst the more abundant intracellular inositol polyphosphates, in chromatin organization, DNA maintenance, gene transcription, nuclear mRNA transport, membrane trafficking and control of cell proliferation. (PMID: 14992690 ).
Structure
Thumb
Synonyms
ValueSource
1D-myo-Inositol 1,3,4,5,6-pentakisphosphateChEBI
D-myo-Inositol 1,3,4,5,6-pentakisphosphateChEBI
Inositol 1,3,4,5,6-pentakisphosphateChEBI
1D-myo-Inositol 1,3,4,5,6-pentakisphosphoric acidGenerator
myo-Inositol 1,3,4,5,6-pentakisphosphoric acidGenerator
D-myo-Inositol 1,3,4,5,6-pentakisphosphoric acidGenerator
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
Chemical FormulaC6H17O21P5
Average Molecular Weight580.0554
Monoisotopic Molecular Weight579.895040166
IUPAC Name{[(1S,2r,3R,4S,5r,6R)-2-hydroxy-3,4,5,6-tetrakis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional Nameinositol pentaphosphate
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 KeyInChIKey=CTPQAXVNYGZUAJ-KXXVROSKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as inositol phosphates. These are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassAlcohols and polyols
Sub ClassCyclic alcohols and derivatives
Direct ParentInositol phosphates
Alternative Parents
Substituents
  • Inositol phosphate
  • Monoalkyl phosphate
  • Cyclohexanol
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Secondary alcohol
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Nucleus
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity90.14 m3·mol-1ChemAxon
Polarizability38.48 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Nucleus
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Inositol MetabolismSMP00011map00562
Inositol Phosphate MetabolismSMP00462map00562
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023187
KNApSAcK IDNot Available
Chemspider ID10333900
KEGG Compound IDC01284
BioCyc IDNot Available
BiGG ID37275
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03529
Metagene LinkHMDB03529
METLIN IDNot Available
PubChem CompoundNot Available
PDB ID5MY
ChEBI ID16322
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. [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. [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 + 1D-Myo-inositol 1,4,5,6-tetrakisphosphate → ADP + Inositol 1,3,4,5,6-pentakisphosphatedetails
Adenosine triphosphate + Inositol 1,4,5-trisphosphate → ADP + 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 + 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 → Inositol 1,3,4,5,6-pentakisphosphate + Adenosine triphosphatedetails