Inositol 1,4,5-Trisphosphate
PubChem CID
439456
Structure
Molecular Formula
Synonyms
- inositol 1,4,5-trisphosphate
- 85166-31-0
- d-myo-inositol-1,4,5-triphosphate
- 1,4,5-Insp3
- InsP3
Molecular Weight
420.10 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2004-09-16
- Modify:2025-01-18
Description
1D-myo-inositol 1,4,5-trisphosphate is a myo-inositol trisphosphate. It has a role as a mouse metabolite. It is a conjugate acid of a 1D-myo-inositol 1,4,5-trisphosphate(6-).
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. 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.
d-Myo-inositol-1,4,5-triphosphate has been reported in Homo sapiens with data available.
Chemical Structure Depiction
[(1R,2S,3R,4R,5S,6R)-2,3,5-trihydroxy-4,6-diphosphonooxycyclohexyl] dihydrogen phosphate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
MMWCIQZXVOZEGG-XJTPDSDZSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
[C@H]1([C@@H]([C@H]([C@@H]([C@H]([C@@H]1OP(=O)(O)O)O)OP(=O)(O)O)OP(=O)(O)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C6H15O15P3
Computed by PubChem 2.2 (PubChem release 2021.10.14)
- 1,4,5-InsP3
- 1,4,5-IP3
- Inositol 1,4,5-Triphosphate
- Inositol 1,4,5-Trisphosphate
- Myo-Inositol 1,4,5-Trisphosphate
- Myoinositol 1,4,5-Triphosphate
- inositol 1,4,5-trisphosphate
- 85166-31-0
- d-myo-inositol-1,4,5-triphosphate
- 1,4,5-Insp3
- InsP3
- 1D-myo-Inositol 1,4,5-trisphosphate
- D-myo-Inositol 1,4,5-trisphosphate
- Ins(1,4,5)P3
- Triphosphoinositol
- Inositol trisphosphate
- IP3
- D-myo-Inositol, 1,4,5-tris(dihydrogen phosphate)
- myo-Inositol 1,4,5-trisphosphate
- myo-Inositol triphosphate
- 142656-03-9
- 1,4,5-IP3
- Ionositol 1,4,5-triphosphate
- CHEMBL279107
- CHEBI:16595
- DTXSID80893598
- 1D-myo-inositol 1,4,5-tris(dihydrogen phosphate)
- D-myo-Inositol 1,4,5-triphosphate
- Inositol 1,4,5-triphosphate
- [(1R,2S,3R,4R,5S,6R)-2,3,5-trihydroxy-4,6-diphosphonooxycyclohexyl] dihydrogen phosphate
- I3P
- {[(1R,2S,3R,4R,5S,6R)-2,3,5-trihydroxy-4,6-bis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
- MU34XVK5NR
- myo-inositol 1,4,5-triphosphate
- Myoinositol 1,4,5-Triphosphate
- 1btn
- 1mai
- 1h0a
- 1n4k
- myo-Inositol trisphosphate
- Inositol 1,4,5 Trisphosphate
- GTPL4222
- SCHEMBL9383914
- D-MYO-INOSITOL-1,4,5-TRIPHOSPHATE, TRIPOTASSIUM SALT
- DTXCID601473971
- Inositol triphosphate (6CI,7CI)
- 88269-39-0
- CMC_6811
- CMC_7228
- Inositol 1,4,5-trisphosphoric acid
- BDBM50075183
- CMC_10501
- CMC_11728
- CMC_11837
- CMC_12664
- CMC_12735
- 1D-myo-inositol 1,4,5-triphosphate
- DB03401
- D-Myo-inositol 1,4,5-trisphosphoric acid
- D-MYO-inositol-1,4,5-triphosphoric acid
- 1D-Myo-inositol 1,4,5-trisphosphoric acid
- NS00069766
- 3,5,6-trioxyphosphate-1,2,4-cyclohexanetriol
- C01245
- Q26998374
- 1,2,3,4,5,6-cyclohexanehexol, 1,2,4-tris(dihydrogen phosphate)
- (1R,2R,3S,4R,5R,6S)-3,5,6-trihydroxycyclohexane-1,2,4-triyl tris[dihydrogen (phosphate)]
- [(1R,2S,3R,4R,5S,6R)-2,3,5-trihydroxy-4,6-diphosphonooxy-cyclohexyl] dihydrogen phosphate
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
420.10 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-7
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
15
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
419.96238076 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
419.96238076 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
261 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
24
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
574
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
6
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
Solid
Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
Spectra ID
Instrument Type
n/a
Ionization Mode
negative
Top 5 Peaks
241.0 82.41
321.0 14.74
158.9 2.85
Notes
adduct_type [339.0]- original_collision_energy 35 % nominal CannabisDB spectra from NIST14 2020 June Thermo Finnigan Elite Orbitrap
Spectra ID
Instrument Type
n/a
Ionization Mode
negative
Top 5 Peaks
79.0 43.53
97.0 31.42
223.0 25.04
Notes
adduct_type [241.0]- original_collision_energy 35 % nominal CannabisDB spectra from NIST14 2020 June Thermo Finnigan Elite Orbitrap
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Stereo Count
Same Isotope Count
Same Parent, Connectivity Count
Same Parent, Stereo Count
Same Parent, Isotope Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
- Epidermis
- Neuron
- Pancreas
- Platelet
- Spleen
- Cytoplasm
- Nucleus
- Acebutolol Action Pathway
- Acrivastine H1-Antihistamine Action
- Activation of PKC through G protein coupled receptor
- Alcaftadine H1-Antihistamine Action
- Alimemazine H1-Antihistamine Action
- Alprenolol Action Pathway
- Amiodarone Action Pathway
- Amlodipine Action Pathway
- Antazoline H1-Antihistamine Action
- Arbutamine Action Pathway
- Total 147 pathways, visit the HMDB page for details
WormJam Metabolites Local CSV for MetFrag | DOI:10.5281/zenodo.3403364
WormJam: A consensus C. elegans Metabolic Reconstruction and Metabolomics Community and Workshop Series, Worm, 6:2, e1373939, DOI:10.1080/21624054.2017.1373939
Zebrafish Pathway Metabolite MetFrag Local CSV (Beta) | DOI:10.5281/zenodo.3457553
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
- CAS Common ChemistryLICENSEThe data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc/4.0/
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_use1D-myo-inositol 1,4,5-trisphosphatehttps://www.drugbank.ca/drugs/DB03401
- EPA DSSToxInositol 1,4,5-trisphosphatehttps://comptox.epa.gov/dashboard/DTXSID80893598CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- FDA Global Substance Registration System (GSRS)LICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linkingINOSITOL 1,4,5-TRISPHOSPHATEhttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/MU34XVK5NR
- Human Metabolome Database (HMDB)LICENSEHMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.http://www.hmdb.ca/citingmyo-Inositol 1,4,5-trisphosphatehttp://www.hmdb.ca/metabolites/HMDB0001498HMDB0001498_msms_1471711https://hmdb.ca/metabolites/HMDB0001498#spectra
- ChEBI1D-myo-inositol 1,4,5-trisphosphatehttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16595
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/d-Myo-inositol-1,4,5-triphosphatehttps://www.wikidata.org/wiki/Q26998374LOTUS Treehttps://lotus.naturalproducts.net/
- NCI Thesaurus (NCIt)LICENSEUnless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.https://www.cancer.gov/policies/copyright-reuse
- Yeast Metabolome Database (YMDB)Inositol 1,4,5-trisphosphatehttps://www.ymdb.ca/compounds/YMDB00291
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.htmlChEMBL Protein Target Treehttps://www.ebi.ac.uk/chembl/g/#browse/targets
- ClinicalTrials.govLICENSEThe ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
- Comparative Toxicogenomics Database (CTD)LICENSEIt is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.http://ctdbase.org/about/legal.jspInositol 1,4,5-Trisphosphatehttps://ctdbase.org/detail.go?type=chem&acc=D015544
- IUPHAR/BPS Guide to PHARMACOLOGYLICENSEThe Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/)https://www.guidetopharmacology.org/about.jsp#licenseGuide to Pharmacology Target Classificationhttps://www.guidetopharmacology.org/targets.jsp
- Therapeutic Target Database (TTD)D-myo-inositol 1,4,5-trisphosphatehttps://idrblab.net/ttd/data/drug/details/D0MR1K
- ECI Group, LCSB, University of Luxembourg1D-myo-inositol 1,4,5-trisphosphate
- Natural Product Activity and Species Source (NPASS)
- FooDBLICENSEFooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.https://foodb.ca/aboutInositol 1,4,5-trisphosphatehttps://foodb.ca/compounds/FDB022657
- NIST Mass Spectrometry Data CenterLICENSEData covered by the Standard Reference Data Act of 1968 as amended.https://www.nist.gov/srd/public-lawD-myo-Inositol-1,4,5-triphosphatehttp://www.nist.gov/srd/nist1a.cfm
- Japan Chemical Substance Dictionary (Nikkaji)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.html
- Metabolomics WorkbenchInositol 1,4,5-trisphosphatehttps://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=37831
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://creativecommons.org/licenses/by/4.0/Inositol 1,4,5-trisphosphateNORMAN Suspect List Exchange Classificationhttps://www.norman-network.com/nds/SLE/
- PharmGKBLICENSEPharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).https://www.pharmgkb.org/page/policiesinositol 1,4,5-trisphosphatehttps://www.pharmgkb.org/chemical/PA166163464
- Protein Data Bank in Europe (PDBe)
- RCSB Protein Data Bank (RCSB PDB)LICENSEData files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.https://www.rcsb.org/pages/policies
- SpectraBaseD-MYO-INOSITOL-1,4,5-TRISPHOSPHATEhttps://spectrabase.com/spectrum/3eXZCF7Xt73D-MYO-INOSITOL-1,4,5-TRISPHOSPHATEhttps://spectrabase.com/spectrum/Br49S0zKc0v
- Wikidata
- WikipediaInositol trisphosphatehttps://en.wikipedia.org/wiki/Inositol_trisphosphate
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlInositol 1,4,5-Trisphosphatehttps://www.ncbi.nlm.nih.gov/mesh/68015544
- PubChem
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- NCBI
CONTENTS