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Record Information
Creation Date2006-08-13 05:55:54 UTC
Update Date2016-02-11 01:06:26 UTC
Secondary Accession Numbers
  • HMDB06233
Metabolite Identification
Common NameD-Myo-inositol 3,4,5,6-tetrakisphosphate
DescriptionInositol phosphates are a family of water-soluble intracellular signaling molecules derived from membrane inositol phospholipids. They undergo a variety of complex interconversion pathways, and their levels are dynamically regulated within the cytosol in response to a variety of agonists. D-Myo-inositol (3,4,5,6) tetrakisphosphate (Ins(3,4,5,6)P4) has a direct biphasic (activation/inhibition) effect on an epithelial Ca2+-activated chloride channel. The effect of Ins(3,4,5,6)P4 is not mimicked by other inositol tetrakisphosphate isomers, is dependent on the prevailing calcium concentration, and is influenced when channels are phosphorylated by calmodulin kinase II. The predominant effect of Ins(3,4,5,6)P4 on phosphorylated channels is inhibitory at levels of intracellular calcium observed in stimulated cells. Ins(3,4,5,6)P4 activity acts to inhibit calcium-dependent chloride secretion. The secretion of fluid and electrolytes across intestinal epithelial cells in response to Ca2+-dependent secretagogues is a tightly regulated process that is subject to both positive and negative influences. Agonists of Gq protein-coupled receptor (GqPCRs) appear to have the ability to evoke antisecretory mechanisms. One is mediated by the generation of Ins(3,4,5,6)P4 and serves to chronically downregulate epithelial responsiveness to subsequent challenge with Ca2+-dependent agonists. (PMID: 12388102 , 11408264 ).
D-myo-Inositol 3,4,5,6-tetrakisphosphateChEBI
D-myo-Inositol 3,4,5,6-tetrakisphosphoric acidGenerator
1D-myo-Inositol 3,4,5,6-tetrakisphosphoric acidGenerator
Inositol-3,4,5,6-tetraphosphoric acidGenerator
myo-Inositol-3,4,5,6-tetrakisphosphoric acidGenerator
D-myo-Inositol, 3,4,5,6-tetrakis(dihydrogen phosphate)HMDB
Inositol 3,4,5,6-tetrakisphosphateHMDB
Chemical FormulaC6H16O18P4
Average Molecular Weight500.0755
Monoisotopic Molecular Weight499.928709756
IUPAC Name{[(1S,2R,3S,4S,5R,6R)-2,3-dihydroxy-4,5,6-tris(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional Name[(1S,2R,3S,4S,5R,6R)-2,3-dihydroxy-4,5,6-tris(phosphonooxy)cyclohexyl]oxyphosphonic acid
CAS Registry Number112791-61-4
InChI Identifier
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
  • Inositol phosphate
  • Monoalkyl phosphate
  • Cyclohexanol
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Secondary alcohol
  • 1,2-diol
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
StatusExpected but not Quantified
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-7.268Not Available
Predicted Properties
Water Solubility11.5 mg/mLALOGPS
pKa (Strongest Acidic)0.24ChemAxon
Physiological Charge-8ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area307.5 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity79.27 m3·mol-1ChemAxon
Polarizability33.99 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
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 IDFDB023236
KNApSAcK IDNot Available
Chemspider ID108765
KEGG Compound IDC04520
BioCyc IDNot Available
BiGG ID43973
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03848
Metagene LinkHMDB03848
METLIN IDNot Available
PubChem Compound121920
ChEBI ID15844
Synthesis ReferenceMorgan Adam J; Komiya Shio; Xu Yingju; Miller Scott J Unified total syntheses of the inositol polyphosphates: D-I-3,5,6P3, D-I-3,4,5P3, D-I-3,4,6P3, and D-I-3,4,5,6P4 via catalytic enantioselective and site-selective phosphorylation. The Journal of organic chemistry (2006), 71(18), 6923-31.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Keely SJ, Barrett KE: p38 mitogen-activated protein kinase inhibits calcium-dependent chloride secretion in T84 colonic epithelial cells. Am J Physiol Cell Physiol. 2003 Feb;284(2):C339-48. Epub 2002 Oct 3. [12388102 ]
  2. Chang N, Uribe JM, Keely SJ, Calandrella S, Barrett KE: Insulin and IGF-I inhibit calcium-dependent chloride secretion by T84 human colonic epithelial cells. Am J Physiol Gastrointest Liver Physiol. 2001 Jul;281(1):G129-37. [11408264 ]


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:
Uniprot ID:
Molecular weight:
Adenosine triphosphate + D-Myo-inositol 3,4,5,6-tetrakisphosphate → ADP + 1D-myo-inositol 1,3,4,5,6-pentakisphosphatedetails
Adenosine triphosphate + D-Myo-inositol 3,4,5,6-tetrakisphosphate → ADP + Inositol 1,3,4,5,6-pentakisphosphatedetails