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Showing metabocard for D-myo-Inositol 3,4,5,6-tetrakisphosphate (HMDB0003848)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 05:55:54 UTC
Update Date2020-02-26 21:24:48 UTC
HMDB IDHMDB0003848
Secondary Accession Numbers
  • HMDB0006233
  • HMDB03848
  • HMDB06233
Metabolite Identification
Common NameD-myo-Inositol 3,4,5,6-tetrakisphosphate
DescriptionInositol phosphates are a family of water-soluble intracellular signalling 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, also known as 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 challenges with Ca2+-dependent agonists (PMID: 12388102 , 11408264 ).
Structure
Data?1582752288
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Inositol-3,4,5,6-tetraphosphateChEBI
Ins-3,4,5,6-P4ChEBI
Myo-inositol-3,4,5,6-tetrakisphosphateChEBI
Inositol 3,4,5,6-tetrakisphosphateKegg
Inositol-3,4,5,6-tetraphosphoric acidGenerator
Myo-inositol-3,4,5,6-tetrakisphosphoric acidGenerator
Inositol 3,4,5,6-tetrakisphosphoric acidGenerator
D-Myo-inositol 3,4,5,6-tetrakisphosphoric acidGenerator
1D-Myo-inositol 3,4,5,6-tetrakisphosphateHMDB
D-Myo-inositol, 3,4,5,6-tetrakis(dihydrogen phosphate)HMDB
Ins(3,4,5,6)P3HMDB
D-myo-Inositol 3,4,5,6-tetrakisphosphateHMDB
D-myo-Inositol 3,4,5,6-tetraphosphateHMDB
Inositol 3,4,5,6-tetrakis(phosphate)HMDB
Inositol 3,4,5,6-tetraphosphateHMDB
Ins(3,4,5,6)P4HMDB
Chemical FormulaC6H16O18P4
Average Molecular Weight500.0755
Monoisotopic Molecular Weight499.928709756
IUPAC Name{[(1R,2S,3R,4S,5S,6R)-3,4-dihydroxy-2,5,6-tris(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional Name[(1R,2S,3R,4S,5S,6R)-3,4-dihydroxy-2,5,6-tris(phosphonooxy)cyclohexyl]oxyphosphonic acid
CAS Registry Number112791-61-4
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+/m0/s1
InChI KeyMRVYFOANPDTYBY-UZAAGFTCSA-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:

Process

Naturally occurring process:

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
Polarizability33.99 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, Positivesplash10-0002-9122600000-383a9e0d030e04f9efbcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fdk-9721484000-b7d5efdc25d786b39d17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-5000790000-5390e100a7edacead23dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-3000940000-553717cc294ea575f253Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pba-3109000000-2fceafe8a79fc5fd8156Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-3000900000-724d0d2ad6f25c90d193Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9002100000-815d445436dd2d0ccdbcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-2dc66a8603e5713437a3Spectrum
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 IDFDB023236
KNApSAcK IDNot Available
Chemspider ID108765
KEGG Compound IDC04520
BioCyc IDNot Available
BiGG ID43973
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound121920
PDB IDNot Available
ChEBI ID15844
Food Biomarker OntologyNot Available
VMH IDMI3456P
References
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. [PubMed: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. [PubMed:11408264 ]

Enzymes

Enzyme Details
1. Inositol-tetrakisphosphate 1-kinase
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 + 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