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discounted EARLY registration ends Dec 31, 2014
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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 Sun Dec 21, 2014, biocyc14.