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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 20:34:43 UTC
Update Date2019-07-23 05:46:13 UTC
HMDB IDHMDB0004527
Secondary Accession Numbers
  • HMDB04527
Metabolite Identification
Common Name1D-Myo-inositol 1,4,5,6-tetrakisphosphate
Description1D-Myo-inositol 1,4,5,6-tetrakisphosphate has been shown to regulate Cl- transport, to be a phosphoinositide 3-kinase antagonist, and to bind tightly to some pleckstrin homology domains, and finally, it may contribute to transcriptional regulation. Inositol phosphates comprise a large family of intracellular signals which play many important roles in cell biology. These biological actions can be quite specific to one particular inositol phosphate. 1D-myo-Inositol 1,4,5,6-tetrakisphosphate (Ins(1,4,5,6)P4) is phosphorylated by inositolphosphate-multikinase (IPMK; this enzyme has the capacity to regulate the cellular levels of Ins(1,4,5,6)P4 in mammalian cells. (PMID: 16376887 , 10720331 , 8809047 , 9405634 ).
Structure
Data?1563860773
Synonyms
ValueSource
D-Myo-inositol 1,4,5,6-tetrakisphosphateChEBI
Inositol 1,4,5,6-tetrakisphosphateChEBI
D-Myo-inositol 1,4,5,6-tetrakisphosphoric acidGenerator
Inositol 1,4,5,6-tetrakisphosphoric acidGenerator
1D-Myo-inositol 1,4,5,6-tetrakisphosphoric acidGenerator
Ins(1,4,5,6)P3HMDB
Chemical FormulaC6H16O18P4
Average Molecular Weight500.0755
Monoisotopic Molecular Weight499.928709756
IUPAC Name{[(1R,2R,3S,4R,5S,6S)-2,3-dihydroxy-4,5,6-tris(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional Name[(1R,2R,3S,4R,5S,6S)-2,3-dihydroxy-4,5,6-tris(phosphonooxy)cyclohexyl]oxyphosphonic acid
CAS Registry Number121010-58-0
SMILES
O[C@H]1[C@@H](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/C6H16O18P4/c7-1-2(8)4(22-26(12,13)14)6(24-28(18,19)20)5(23-27(15,16)17)3(1)21-25(9,10)11/h1-8H,(H2,9,10,11)(H2,12,13,14)(H2,15,16,17)(H2,18,19,20)/t1-,2+,3-,4-,5+,6+/m1/s1
InChI KeyMRVYFOANPDTYBY-YORTWTKJSA-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
  • 1,2-diol
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-7.268Not Available
Predicted Properties
PropertyValueSource
Water Solubility11.5 g/LALOGPS
logP-0.45ALOGPS
logP-4.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)0.24ChemAxon
Physiological Charge-8ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area307.5 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity79.27 m³·mol⁻¹ChemAxon
Polarizability34.03 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9122400000-491cb901d4da4438adcdJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fka-9613563000-db65528e199a9ef0a1deJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-3001890000-6d29fe43af2dfe333746JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-2001940000-a2d065ccf972f5a0d31eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-3229000000-9cd7e10c0f436d320056JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-3000900000-566dc92f1bd23a27ac86JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000300000-cf0d92f7ca1ea1c60f4eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-cff85d73f31b0c0695c3JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
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
FoodDB IDFDB023378
KNApSAcK IDNot Available
Chemspider ID391520
KEGG Compound IDC11555
BioCyc IDNot Available
BiGG ID2264980
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound443266
PDB IDNot Available
ChEBI ID16067
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Riley AM, Deleu S, Qian X, Mitchell J, Chung SK, Adelt S, Vogel G, Potter BV, Shears SB: On the contribution of stereochemistry to human ITPK1 specificity: Ins(1,4,5,6)P4 is not a physiologic substrate. FEBS Lett. 2006 Jan 9;580(1):324-30. Epub 2005 Dec 19. [PubMed:16376887 ]
  2. Odom AR, Stahlberg A, Wente SR, York JD: A role for nuclear inositol 1,4,5-trisphosphate kinase in transcriptional control. Science. 2000 Mar 17;287(5460):2026-9. [PubMed:10720331 ]
  3. Takeuchi H, Kanematsu T, Misumi Y, Yaakob HB, Yagisawa H, Ikehara Y, Watanabe Y, Tan Z, Shears SB, Hirata M: Localization of a high-affinity inositol 1,4,5-trisphosphate/inositol 1,4,5,6-tetrakisphosphate binding domain to the pleckstrin homology module of a new 130 kDa protein: characterization of the determinants of structural specificity. Biochem J. 1996 Sep 1;318 ( Pt 2):561-8. [PubMed:8809047 ]
  4. Eckmann L, Rudolf MT, Ptasznik A, Schultz C, Jiang T, Wolfson N, Tsien R, Fierer J, Shears SB, Kagnoff MF, Traynor-Kaplan AE: D-myo-Inositol 1,4,5,6-tetrakisphosphate produced in human intestinal epithelial cells in response to Salmonella invasion inhibits phosphoinositide 3-kinase signaling pathways. Proc Natl Acad Sci U S A. 1997 Dec 23;94(26):14456-60. [PubMed:9405634 ]

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