Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-08-13 05:55:54 UTC |
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Update Date | 2020-05-14 21:05:49 UTC |
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HMDB ID | HMDB0003848 |
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Secondary Accession Numbers | - HMDB0006233
- HMDB03848
- HMDB06233
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Metabolite Identification |
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Common Name | D-myo-Inositol 3,4,5,6-tetrakisphosphate |
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Description | Inositol 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 ). |
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Structure | |
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Synonyms | Value | Source |
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Inositol-3,4,5,6-tetraphosphate | ChEBI | Ins-3,4,5,6-P4 | ChEBI | Myo-inositol-3,4,5,6-tetrakisphosphate | ChEBI | Inositol 3,4,5,6-tetrakisphosphate | Kegg | Inositol-3,4,5,6-tetraphosphoric acid | Generator | Myo-inositol-3,4,5,6-tetrakisphosphoric acid | Generator | Inositol 3,4,5,6-tetrakisphosphoric acid | Generator | D-Myo-inositol 3,4,5,6-tetrakisphosphoric acid | Generator | 1D-Myo-inositol 3,4,5,6-tetrakisphosphate | HMDB | D-Myo-inositol, 3,4,5,6-tetrakis(dihydrogen phosphate) | HMDB | Ins(3,4,5,6)P3 | HMDB | D-Myo-inositol 3,4,5,6-tetraphosphate | HMDB | Inositol 3,4,5,6-tetrakis(phosphate) | HMDB | Inositol 3,4,5,6-tetraphosphate | HMDB | Ins(3,4,5,6)P4 | HMDB | D-myo-Inositol 3,4,5,6-tetrakisphosphate | HMDB |
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Chemical Formula | C6H16O18P4 |
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Average Molecular Weight | 500.0755 |
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Monoisotopic Molecular Weight | 499.928709756 |
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IUPAC Name | {[(1R,2S,3R,4S,5S,6R)-3,4-dihydroxy-2,5,6-tris(phosphonooxy)cyclohexyl]oxy}phosphonic acid |
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Traditional Name | [(1R,2S,3R,4S,5S,6R)-3,4-dihydroxy-2,5,6-tris(phosphonooxy)cyclohexyl]oxyphosphonic acid |
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CAS Registry Number | 112791-61-4 |
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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 |
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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 |
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InChI Key | MRVYFOANPDTYBY-UZAAGFTCSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Alcohols and polyols |
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Direct Parent | Inositol phosphates |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Source: |
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Process | Naturally occurring process: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | -7.268 | Not Available |
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Predicted Properties | |
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Synthesis Reference | Morgan 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. |
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