Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
twitter

MetaCyc Compound: D-myo-inositol (1,4,5)-trisphosphate

Abbrev Name: Ins(1,4,5)P3

Synonyms: inositol (1,4,5)-trisphosphate, 1D-myo-inositol (1,4,5)-trisphosphate, Ins(1,4,5)P3, I(1,4,5)P3, InsP3, IP3, triphosphoinositol

Superclasses: an alcohol a cyclic alcohol a cyclitol an inositol a modified inositol an inositol phosphate a myo-inositol-polyphosphate a myo-inositol trisphosphate

Summary:
D-myo-inositol (1,4,5)-trisphosphate is a secondary messenger molecule used in signal transduction and lipid signaling in eukaryoticl cells. D-myo-inositol (1,4,5)-trisphosphate is soluble and diffuses through the cell. It is synthesized by hydrolysis of phosphatidylinositol 4,5-bisphosphate (PIP2), a phospholipid that is located in the plasma membrane, by the action of phospholipase C, as described in D-myo-inositol (1,4,5)-trisphosphate biosynthesis.

Chemical Formula: C6H9O15P3

Molecular Weight: 414.05 Daltons

Monoisotopic Molecular Weight: 419.96237934299995 Daltons

SMILES: C1(O)(C(OP([O-])([O-])=O)C(O)C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(O)1)

InChI: InChI=1S/C6H15O15P3/c7-1-2(8)5(20-23(13,14)15)6(21-24(16,17)18)3(9)4(1)19-22(10,11)12/h1-9H,(H2,10,11,12)(H2,13,14,15)(H2,16,17,18)/p-6/t1-,2+,3+,4-,5-,6-/m1/s1

InChIKey: InChIKey=MMWCIQZXVOZEGG-XJTPDSDZSA-H

Unification Links: CAS:85166-31-0 , CAS:88269-39-0 , ChEBI:203600 , ChemSpider:10375590 , HMDB:HMDB01498 , KEGG:C01245 , MetaboLights:MTBLC203600 , PubChem:21761708 , Wikipedia:Inositol_triphosphate

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -776.2541 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

1D-myo-inositol hexakisphosphate biosynthesis I (from Ins(1,4,5)P3) :
D-myo-inositol (1,4,5)-trisphosphate + ATP → D-myo-inositol (1,4,5,6)-tetrakisphosphate + ADP + H+
D-myo-inositol (1,4,5)-trisphosphate + ATP → D-myo-inositol (1,3,4,5)-tetrakisphosphate + ADP + H+

1D-myo-inositol hexakisphosphate biosynthesis II (mammalian) , D-myo-inositol (1,3,4)-trisphosphate biosynthesis :
D-myo-inositol (1,4,5)-trisphosphate + ATP → D-myo-inositol (1,3,4,5)-tetrakisphosphate + ADP + H+

D-myo-inositol (1,4,5)-trisphosphate degradation :
D-myo-inositol (1,4,5)-trisphosphate + H2O → D-myo-inositol (1,4)-bisphosphate + phosphate

Not in pathways:
a cyclic alcohol + a quinone → a cyclic ketone + a quinol

Reactions known to produce the compound:

D-myo-inositol (1,3,4)-trisphosphate biosynthesis :
D-myo-inositol (1,3,4,5)-tetrakisphosphate + H2O → D-myo-inositol (1,4,5)-trisphosphate + phosphate

D-myo-inositol (1,4,5)-trisphosphate biosynthesis , D-myo-inositol-5-phosphate metabolism , phosphatidate metabolism, as a signaling molecule , phospholipases :
a 1-phosphatidyl-1D-myo-inositol 4,5-bisphosphate + H2O → a 1,2-diacyl-sn-glycerol + D-myo-inositol (1,4,5)-trisphosphate + H+

Not in pathways:
D-myo-inositol (1,4,5,6)-tetrakisphosphate + H2O → D-myo-inositol (1,4,5)-trisphosphate + phosphate

β-D-glucuronide and D-glucuronate degradation :
a β-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol

glycerophosphodiester degradation :
a glycerophosphodiester + H2O → an alcohol + sn-glycerol 3-phosphate + H+

phosphate acquisition , phosphate utilization in cell wall regeneration :
a phosphate monoester + H2O ↔ an alcohol + phosphate


an alcohol + NAD+ + H2O ← an organic hydroperoxide + NADH + H+
an α-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol
an α amino acid ester + H2O → an alcohol + an α amino acid + H+
a phosphate monoester + H2O → an alcohol + phosphate
RH + a reduced [NADPH-hemoprotein reductase] + oxygen → ROH + an oxidized [NADPH-hemoprotein reductase] + H2O
an oligosaccharide with β-L-arabinopyranose at the non-reducing end + H2O → β-L-arabinopyranose + an alcohol
an N-acetyl-β-D-hexosaminide + H2O → an N-acetyl-β-D-hexosamine + an alcohol
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an acetic ester + H2O → an alcohol + acetate + H+
a reduced thioredoxin + an organic hydroperoxide → an oxidized thioredoxin + an alcohol + H2O
a 6-O-(β-D-xylopyranosyl)-β-D-glucopyranoside + H2O → β-primeverose + an alcohol
an organic molecule + H2O + 2 oxygen → an alcohol + 2 superoxide + 2 H+
an N5-acyl-L-ornithine-ester + H2O → an N5-acyl-L-ornithine + an alcohol
α-L-fucoside + H2O → L-fucopyranose + an alcohol
a 2-deoxy-α-D-glucoside + H2O → 2-deoxy-D-glucose + an alcohol
a 6-phospho-β-D-galactoside + H2O → α-D-galactose 6-phosphate + an alcohol

In Reactions of unknown directionality:

Not in pathways:
D-myo-inositol (4,5)-bisphosphate + ATP = D-myo-inositol (1,4,5)-trisphosphate + ADP + H+
D-myo-inositol (1,4,5)-trisphosphate + 2 ATP = D-myo-inositol 1,3,4,5,6-pentakisphosphate + 2 ADP + 2 H+


a pyrophosphate-containing inositol phosphate + H2O = a myo-inositol-polyphosphate + phosphate


an alcohol + 3'-phosphoadenylyl-sulfate = adenosine 3',5'-bisphosphate + an organosulfate + H+
an alcohol + NAD(P)+ = an aldehyde + NAD(P)H + H+
an alcohol + NADP+ = an aldehyde + NADPH + H+
trans-cinnamoyl-β-D-glucoside + an alcohol = β-D-glucose + alkyl cinnamate
an alcohol + acetyl-CoA = an acetic ester + coenzyme A
2 protein cysteines + an organic hydroperoxide = a protein disulfide + an alcohol + H2O
an organic molecule + an organic hydroperoxide = 2 an alcohol
an organic molecule + hydrogen peroxide = an alcohol + H2O

Enzymes activated by D-myo-inositol (1,4,5)-trisphosphate, sorted by the type of activation, are:

Activator (Mechanism unknown) of: phosphoenolpyruvate carboxylase [Izui83]

Credits:
Revised 09-Oct-2009 by Caspi R , SRI International


References

Izui83: Izui K, Matsuda Y, Kameshita I, Katsuki H, Woods AE (1983). "Phosphoenolpyruvate carboxylase of Escherichia coli. Inhibition by various analogs and homologs of phosphoenolpyruvate." J Biochem (Tokyo) 1983;94(6);1789-95. PMID: 6368527

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Lecompte08: Lecompte O, Poch O, Laporte J (2008). "PtdIns5P regulation through evolution: roles in membrane trafficking?." Trends Biochem Sci 33(10);453-60. PMID: 18774718

Rohde02: Rohde G, Wenzel D, Haucke V (2002). "A phosphatidylinositol (4,5)-bisphosphate binding site within mu2-adaptin regulates clathrin-mediated endocytosis." J Cell Biol 158(2);209-14. PMID: 12119359


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Fri Nov 28, 2014, BIOCYC13A.