Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2019-07-23 05:44:42 UTC |
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HMDB ID | HMDB0001059 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Inositol 1,3,4,5-tetraphosphate |
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Description | Inositol 1,3,4,5-tetrakisphopsphate (IP4) is a second messenger responsible for mediating Ca2+ entry through plasma membrane and mobilize intracellular Ca2+ by acting synergistically with inositol 1,4,5-trisphosphate (IP3). Inositol 1,4,5-trisphosphate 3-kinase (IP3K, EC 2.7.1.127) phosphorylates IP3 to IP4. Evidence shows that IP4 can activate a protein with ras- and rap-GAP activity and finally inactivate the G protein. This indicates that IP4 regulates Ca2+ influx in a GTP-dependent way, which potentially links the IP3 signaling pathway to GTP-regulated signaling mechanisms. IP4 is demonstrated to be a common regulator in Ca2+ homeostasis. IP4 can bind with high affinity to several intracellular proteins: synaptotagmin (I and II), Gap1, Btk, and centaurin-alpha-and may interact with synaptotagmin to inhibit synaptic transmission. IP4 also acts as a mediator in neuronal death in the ischemic hippocampus. IP4 production is not always associated with modification in calcium concentration, and control of calcium mobilization is not the sole function proposed for IP4. IP4 define an essential signaling pathway for T cell precursor responsiveness and development. In the thymus, IP4 is essential during positive and negative selection of double-positive thymocytes, and in the control of thymocyte reactivity to antigens. 1D-Myo-inositol 1,3,4,5-tetrakisphosphate is also a substrate for Type I inositol-1,4,5-trisphosphate 5-phosphatase, Phosphatidylinositol 4,5-bisphosphate 5-phosphatase A and Skeletal muscle and kidney enriched inositol phosphatase. (PMID: 15740635 , 14517551 ). |
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Structure | |
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Synonyms | Value | Source |
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Inositol 1,3,4,5-tetraphosphoric acid | Generator | 1,3,4,5-Tetrakis(dihydrogen phosphate) myo-inositol | HMDB | 1D-Myo-inositol 1,3,4,5-tetrakis(dihydrogen phosphate) | HMDB | 1D-Myo-inositol 1,3,4,5-tetrakisphosphate | HMDB | D-Myo-inositol 1,3,4,5-tetrakisphosphate | HMDB | Inositol 1,3,4,5-tetrakis(phosphate) | HMDB | Inositol 1,3,4,5-tetrakisphosphate | HMDB | Inositol-(1,3,4,5)-tetrakisphosphate | HMDB | Inositol-1,3,4,5-tetrakisphosphate | HMDB | Inositol-1,3,4,5-tetraphosphate | HMDB | Ins-1,3,4,5-P4 | HMDB | Myo-inositol 1,3,4,5-tetrakis(phosphate) | HMDB | Myo-inositol 1,3,4,5-tetraphosphate | HMDB | Myo-inositol, 1,3,4,5-tetrakis(dihydrogen phosphate) | HMDB | Myo-inositol-1,3,4,5-tetrakisphosphate | HMDB | [(2R,3S,5S,6S)-3,5-Dihydroxy-2,4,6-triphosphonooxycyclohexyl] dihydrogen phosphate | HMDB | Inositol-1,3,4,5-tetrakisphosphate, DL-isomer | HMDB | Ins(1,3,4,5)p(4) | HMDB | Inositol-1,3,4,5-tetrakisphosphate, D-isomer | HMDB | Ins(1,3,4,5)P4 | 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 | {[(2S,3R,5S,6S)-2,6-dihydroxy-3,4,5-tris(phosphonooxy)cyclohexyl]oxy}phosphonic acid |
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Traditional Name | [(2S,3R,5S,6S)-2,6-dihydroxy-3,4,5-tris(phosphonooxy)cyclohexyl]oxyphosphonic acid |
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CAS Registry Number | 102850-29-3 |
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SMILES | O[C@H]1C(OP(O)(O)=O)[C@H](O)[C@@H](OP(O)(O)=O)C(OP(O)(O)=O)[C@H]1OP(O)(O)=O |
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InChI Identifier | InChI=1S/C6H16O18P4/c7-1-3(21-25(9,10)11)2(8)5(23-27(15,16)17)6(24-28(18,19)20)4(1)22-26(12,13)14/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 | CIPFCGZLFXVXBG-FTSGZOCFSA-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
- Organic oxide
- Hydrocarbon derivative
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Biological location: Source: |
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Role | Biological role: |
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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 | Not Available | Not Available |
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Predicted Properties | |
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Synthesis Reference | DeSolms, S. Jane; Vacca, Joseph P.; Huff, Joel R. The total synthesis of (±)-myo-inositol-1,3,4-triphosphate, (±)-myo-inositol-2,4,5-triphosphate and (±)-myo-inositol-1,3,4,5-tetraphosphate. Tetrahedron Letters (1987), 28(39), 4503-6. |
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General References | - Cozier GE, Lockyer PJ, Reynolds JS, Kupzig S, Bottomley JR, Millard TH, Banting G, Cullen PJ: GAP1IP4BP contains a novel group I pleckstrin homology domain that directs constitutive plasma membrane association. J Biol Chem. 2000 Sep 8;275(36):28261-8. [PubMed:10869341 ]
- Horne G, Potter BV: Synthesis of the enantiomers of 6-deoxy-myo-inositol 1,3,4,5-tetrakisphosphate, structural analogues of myo-inositol 1,3,4,5-tetrakisphosphate. Chemistry. 2001 Jan 5;7(1):80-7. [PubMed:11205029 ]
- Han SY, Kato H, Kato S, Suzuki T, Shibata H, Ishii S, Shiiba K, Matsuno S, Kanamaru R, Ishioka C: Functional evaluation of PTEN missense mutations using in vitro phosphoinositide phosphatase assay. Cancer Res. 2000 Jun 15;60(12):3147-51. [PubMed:10866302 ]
- Xia HJ, Yang G: Inositol 1,4,5-trisphosphate 3-kinases: functions and regulations. Cell Res. 2005 Feb;15(2):83-91. [PubMed:15740635 ]
- Pouillon V, Hascakova-Bartova R, Pajak B, Adam E, Bex F, Dewaste V, Van Lint C, Leo O, Erneux C, Schurmans S: Inositol 1,3,4,5-tetrakisphosphate is essential for T lymphocyte development. Nat Immunol. 2003 Nov;4(11):1136-43. Epub 2003 Sep 28. [PubMed:14517551 ]
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