Inositol 1,4,5-trisphosphate (CHEM035245)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:36:16 UTC
Update Date2016-11-09 01:21:16 UTC
Accession NumberCHEM035245
Identification
Common NameInositol 1,4,5-trisphosphate
ClassSmall Molecule
DescriptionIntracellular 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. Inositol 1,4,5-trisphosphate 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.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1,4,5-Insp3ChEBI
D-Myo-inositol 1,4,5-trisphosphateChEBI
D-MYO-inositol-1,4,5-triphosphATEChEBI
Ins(1,4,5)P3ChEBI
InsP3ChEBI
IP3ChEBI
1D-Myo-inositol 1,4,5-trisphosphateKegg
D-Myo-inositol 1,4,5-trisphosphoric acidGenerator
D-MYO-inositol-1,4,5-triphosphoric acidGenerator
1D-Myo-inositol 1,4,5-trisphosphoric acidGenerator
Inositol 1,4,5-trisphosphoric acidGenerator
Myo-inositol 1,4,5-trisphosphateHMDB
1,4,5-IP3HMDB
Inositol 1,4,5-triphosphateHMDB
Myoinositol 1,4,5-triphosphateHMDB
D-myo-Inositol 1,4,5-triphosphateHMDB
IP 3HMDB
Inositol 1,4,5-trisphosphateHMDB
Inositol triphosphateHMDB
Inositol trisphosphateHMDB
TriphosphoinositolHMDB
myo-Inositol 1,4,5-triphosphateHMDB
myo-Inositol triphosphateHMDB
myo-Inositol trisphosphateHMDB
Chemical FormulaC6H15O15P3
Average Molecular Mass420.096 g/mol
Monoisotopic Mass419.962 g/mol
CAS Registry Number85166-31-0
IUPAC Name{[(1R,2S,3R,4R,5S,6R)-2,3,5-trihydroxy-4,6-bis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional NameInsP3
SMILESO[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
InChI IdentifierInChI=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
InChI KeyMMWCIQZXVOZEGG-XJTPDSDZSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentInositol phosphates
Alternative Parents
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
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility14.8 g/LALOGPS
logP-0.86ALOGPS
logP-4.2ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)0.54ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-6ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area260.97 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity68.39 m³·mol⁻¹ChemAxon
Polarizability29.61 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002b-7195200000-2871156f7c1e00704088Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0002-9052133000-5094b6ef55759c5a19ddSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-0006-0091000000-66258d5943e8e34a4f1bSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-00ba-9030000000-9567cb0f36d067bd98e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 13V, negativesplash10-0udi-0000900000-a08362b50609e7868113Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 19V, negativesplash10-0udi-0205900000-c9a653bc0177b1f5ec0cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, negativesplash10-0udi-1509800000-0c58a55629c8bdde91c4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 25V, negativesplash10-0zi0-2709200000-f834442aa900d5925ee0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 29V, negativesplash10-0kk9-6908000000-bce10d89581b945182c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 34V, negativesplash10-056r-9603000000-b83a25f979d90dcaacecSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 40V, negativesplash10-004i-9300000000-83996fe12a20b170e2dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 47V, negativesplash10-004i-9100000000-9c6fa50af864d3ab9cccSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-0udi-0109000000-f750488015579ddac395Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-004i-9000000000-0ae8d2338f48c17984cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-0zfr-0970000000-d129d480332834af8631Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-004r-5900000000-4dffa7896e57b68d360eSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-08fr-0639000000-1fc55e97bbb62fd98506Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-0a4i-0943000000-4b6820f7da0e5d559167Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 13V, negativesplash10-014i-0000900000-4422ae3f5c5cbce0813dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 16V, negativesplash10-014i-0103900000-60bb04a7db68b52b301aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 22V, negativesplash10-05fr-1409300000-c28e47a55145868de89dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-3008900000-e987cfb2603d94f1a6a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-2006900000-95047338604f8928313fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-4291000000-8e9bb388f01ec6d535abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-4001900000-395b5e207aa26dd43f27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9003200000-5e6369906fdedd08ad60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4b72b937fe3bf7fe817eSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB03401
HMDB IDHMDB0001498
FooDB IDFDB022657
Phenol Explorer IDNot Available
KNApSAcK IDC00007460
BiGG ID1485108
BioCyc IDINOSITOL-1-4-5-TRISPHOSPHATE
METLIN ID6282
PDB IDNot Available
Wikipedia LinkInositol trisphosphate
Chemspider ID388562
ChEBI ID16595
PubChem Compound ID439456
Kegg Compound IDC01245
YMDB IDYMDB00291
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Cooke, Allan M.; Potter, Barry V. L.; Gigg, Roy. Synthesis of DL-myo-inositol 1,4,5-trisphosphate. Tetrahedron Letters (1987), 28(20), 2305-8.
2. 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.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. Petersen OH, Burdakov D, Tepikin AV: Polarity in intracellular calcium signaling. Bioessays. 1999 Oct;21(10):851-60.
10. 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.
11. 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.
12. 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.
13. 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.
14. 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.
15. 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.
16. 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.
17. 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.
18. 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.
19. 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.
20. Santella L, Lim D, Moccia F: Calcium and fertilization: the beginning of life. Trends Biochem Sci. 2004 Aug;29(8):400-8.