| 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 | 2020-05-15 16:07:13 UTC |
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| HMDB ID | HMDB0001498 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | myo-Inositol 1,4,5-trisphosphate |
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| Description | myo-Inositol 1,4,5-trisphosphate (CAS: 20298-95-7), also known as Ins(1,4,5)P3 or InsP3, is an intracellular messenger formed by the action of phospholipase C on phosphatidylinositol 4,5-bisphosphate, which is one of the phospholipids that make up the cell membrane (PMID: 22453946 ). It is released into the cytoplasm where it releases calcium ions from internal stores within the cell's endoplasmic reticulum. These calcium ions stimulate the activity of B kinase or calmodulin (PMID: 15189149 ). Its transient accumulation is due both to the enhanced metabolism via the Ca2+-calmodulin-sensitive Ins(1,4,5)P3 kinase, as well as a down-regulation of phosphatidylinositol 4,5-bisphosphate hydrolysis (PMID: 3041962 ). It is a major regulator of apoptotic signalling driving calcium (Ca2+) transients from the endoplasmic reticulum to mitochondria, thereby establishing a functional and physical link between these organelles. It also regulates autophagy through the interaction with Beclin 1 complex, and in particular, its inhibition/depletion strongly induces macroautophagy (PMID: 19325567 ). In addition, recent evidence suggests that the penetrating sperm delivers into mammalian eggs a novel isoform of phospholipase C (PLC), which promotes the formation of inositol 1,4,5-trisphosphate (PMID: 15362223 ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| 1,4,5-Insp3 | ChEBI | | D-Myo-inositol 1,4,5-trisphosphate | ChEBI | | D-MYO-inositol-1,4,5-triphosphATE | ChEBI | | Ins(1,4,5)P3 | ChEBI | | InsP3 | ChEBI | | IP3 | ChEBI | | 1D-Myo-inositol 1,4,5-trisphosphate | Kegg | | D-Myo-inositol 1,4,5-trisphosphoric acid | Generator | | D-MYO-inositol-1,4,5-triphosphoric acid | Generator | | 1D-Myo-inositol 1,4,5-trisphosphoric acid | Generator | | Inositol 1,4,5-trisphosphoric acid | Generator | | Myo-inositol 1,4,5-trisphosphate | HMDB | | 1,4,5-IP3 | HMDB | | Inositol 1,4,5-triphosphate | HMDB | | Myoinositol 1,4,5-triphosphate | HMDB | | D-myo-Inositol 1,4,5-triphosphate | HMDB | | IP 3 | HMDB | | Inositol 1,4,5-trisphosphate | HMDB | | Inositol triphosphate | HMDB | | Inositol trisphosphate | HMDB | | Triphosphoinositol | HMDB | | myo-Inositol 1,4,5-triphosphate | HMDB | | myo-Inositol triphosphate | HMDB | | myo-Inositol trisphosphate | HMDB |
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| Chemical Formula | C6H15O15P3 |
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| Average Molecular Weight | 420.0956 |
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| Monoisotopic Molecular Weight | 419.962379346 |
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| IUPAC Name | {[(1R,2S,3R,4R,5S,6R)-2,3,5-trihydroxy-4,6-bis(phosphonooxy)cyclohexyl]oxy}phosphonic acid |
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| Traditional Name | InsP3 |
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| CAS Registry Number | 85166-31-0 |
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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](O)[C@@H]1OP(O)(O)=O |
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| InChI Identifier | 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)/t1-,2+,3+,4-,5-,6-/m1/s1 |
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| InChI Key | MMWCIQZXVOZEGG-XJTPDSDZSA-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
- Polyol
- 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: Biological location: |
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| Process | Naturally occurring process: |
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| Role | Industrial application: 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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| General References | - Nibbering PH, Zomerdijk TP, van Haastert PJ, van Furth R: A competition binding assay for determination of the inositol (1,4,5)-trisphosphate content of human leucocytes. Biochem Biophys Res Commun. 1990 Jul 31;170(2):755-62. [PubMed:2383266 ]
- Brann JH, Dennis JC, Morrison EE, Fadool DA: Type-specific inositol 1,4,5-trisphosphate receptor localization in the vomeronasal organ and its interaction with a transient receptor potential channel, TRPC2. J Neurochem. 2002 Dec;83(6):1452-60. [PubMed:12472899 ]
- Poeckel D, Tausch L, Altmann A, Feisst C, Klinkhardt U, Graff J, Harder S, Werz O: Induction of central signalling pathways and select functional effects in human platelets by beta-boswellic acid. Br J Pharmacol. 2005 Oct;146(4):514-24. [PubMed:16086030 ]
- Koizumi H, Tanaka H, Ohkawara A: beta-Adrenergic stimulation induces activation of protein kinase C and inositol 1,4,5-trisphosphate increase in epidermis. Exp Dermatol. 1997 Jun;6(3):128-32. [PubMed:9226135 ]
- Eberhard M, Erne P: Inositol 1,4,5-trisphosphate-induced calcium release in permeabilized platelets is coupled to hydrolysis of inositol 1,4,5-trisphosphate to inositol 1,4-bisphosphate. Biochem Biophys Res Commun. 1993 Aug 31;195(1):19-24. [PubMed:8363599 ]
- Garlind A, Wiehager B, Winblad B, Fowler CJ: Intracellular inositol (1,4,5)-trisphosphate receptor levels are preserved in Alzheimer's disease platelets. Neurobiol Aging. 1997 Sep-Oct;18(5):559-61. [PubMed:9390785 ]
- Eberhard M, Erne P: Regulation of inositol 1,4,5-trisphosphate-induced calcium release by inositol 1,4,5-trisphosphate and calcium in human platelets. J Recept Signal Transduct Res. 1995 Jan-Mar;15(1-4):297-309. [PubMed:8903946 ]
- Petersen OH, Burdakov D, Tepikin AV: Polarity in intracellular calcium signaling. Bioessays. 1999 Oct;21(10):851-60. [PubMed:10497335 ]
- Arranz B, Rosel P, Sarro S, Ramirez N, Duenas R, Cano R, Maria Sanchez J, San L: Altered platelet serotonin 5-HT2A receptor density but not second messenger inositol trisphosphate levels in drug-free schizophrenic patients. Psychiatry Res. 2003 May 30;118(2):165-74. [PubMed:12798981 ]
- Smith RJ, Justen JM, Nidy EG, Sam LM, Bleasdale JE: Transmembrane signaling in human polymorphonuclear neutrophils: 15(S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid modulates receptor agonist-triggered cell activation. Proc Natl Acad Sci U S A. 1993 Aug 1;90(15):7270-4. [PubMed:8394015 ]
- Laffi G, Marra F, Failli P, Ruggiero M, Cecchi E, Carloni V, Giotti A, Gentilini P: Defective signal transduction in platelets from cirrhotics is associated with increased cyclic nucleotides. Gastroenterology. 1993 Jul;105(1):148-56. [PubMed:8390377 ]
- Kalra R, Singh SP, Kracko D, Matta SG, Sharp BM, Sopori ML: Chronic self-administration of nicotine in rats impairs T cell responsiveness. J Pharmacol Exp Ther. 2002 Sep;302(3):935-9. [PubMed:12183649 ]
- Vanags DM, Lloyd JV, Rodgers SE, Bochner F: ADP, adrenaline and serotonin stimulate inositol 1,4,5-trisphosphate production in human platelets. Eur J Pharmacol. 1998 Sep 25;358(1):93-100. [PubMed:9809874 ]
- Saito H, Nishida A, Shimizu M, Motohashi N, Yamawaki S: Decreased inositol 1,4,5-trisphosphate-specific binding in platelets from alcoholic subjects. Biol Psychiatry. 1996 Nov 1;40(9):886-91. [PubMed:8896775 ]
- Suganuma A, Nakashima S, Okano Y, Nozawa Y: Mass contents of inositol 1,4,5-trisphosphate and 1,2-diacylglycerol in human platelets stimulated with a thromboxane analogue and thrombin. Thromb Haemost. 1992 Sep 7;68(3):341-5. [PubMed:1440502 ]
- Dwivedi Y, Janicak PG, Pandey GN: Elevated [3H]inositol 1,4,5-trisphosphate binding sites and expressed inositol 1,4,5-trisphosphate receptor protein level in platelets of depressed patients. Psychopharmacology (Berl). 1998 Jul;138(1):47-54. [PubMed:9694526 ]
- Willets JM, Nahorski SR, Challiss RA: Roles of phosphorylation-dependent and -independent mechanisms in the regulation of M1 muscarinic acetylcholine receptors by G protein-coupled receptor kinase 2 in hippocampal neurons. J Biol Chem. 2005 May 13;280(19):18950-8. Epub 2005 Mar 2. [PubMed:15743771 ]
- Goncalves I, Hughan SC, Schoenwaelder SM, Yap CL, Yuan Y, Jackson SP: Integrin alpha IIb beta 3-dependent calcium signals regulate platelet-fibrinogen interactions under flow. Involvement of phospholipase C gamma 2. J Biol Chem. 2003 Sep 12;278(37):34812-22. Epub 2003 Jun 27. [PubMed:12832405 ]
- Santella L, Lim D, Moccia F: Calcium and fertilization: the beginning of life. Trends Biochem Sci. 2004 Aug;29(8):400-8. [PubMed:15362223 ]
- Parys JB, De Smedt H: Inositol 1,4,5-trisphosphate and its receptors. Adv Exp Med Biol. 2012;740:255-79. doi: 10.1007/978-94-007-2888-2_11. [PubMed:22453946 ]
- Patterson RL, Boehning D, Snyder SH: Inositol 1,4,5-trisphosphate receptors as signal integrators. Annu Rev Biochem. 2004;73:437-65. doi: 10.1146/annurev.biochem.73.071403.161303. [PubMed:15189149 ]
- Biden TJ, Vallar L, Wollheim CB: Regulation of inositol 1,4,5-trisphosphate metabolism in insulin-secreting RINm5F cells. Biochem J. 1988 Apr 15;251(2):435-40. doi: 10.1042/bj2510435. [PubMed:3041962 ]
- Vicencio JM, Ortiz C, Criollo A, Jones AW, Kepp O, Galluzzi L, Joza N, Vitale I, Morselli E, Tailler M, Castedo M, Maiuri MC, Molgo J, Szabadkai G, Lavandero S, Kroemer G: The inositol 1,4,5-trisphosphate receptor regulates autophagy through its interaction with Beclin 1. Cell Death Differ. 2009 Jul;16(7):1006-17. doi: 10.1038/cdd.2009.34. Epub 2009 Mar 27. [PubMed:19325567 ]
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