1D-myo-inositol 1,4,5-trisphosphate
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Identification
- Generic Name
- 1D-myo-inositol 1,4,5-trisphosphate
- DrugBank Accession Number
- DB03401
- Background
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.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 420.0956
Monoisotopic: 419.962379346 - Chemical Formula
- C6H15O15P3
- Synonyms
- 1,4,5-Insp3
- D-myo-Inositol 1,4,5-trisphosphate
- D-myo-Inositol-1,4,5-triphosphate
- Inositol 1,4,5-trisphosphate
- Ins(1,4,5)P3
- InsP3
- IP3
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AInositol 1,4,5-trisphosphate-gated calcium channel ITPR1 inhibitorHumans AInositol 1,4,5-trisphosphate-gated calcium channel ITPR3 inhibitorHumans AInositol 1,4,5-trisphosphate-gated calcium channel ITPR2 inhibitorHumans UCytohesin-2 Not Available Humans UEpsin-1 Not Available Humans U1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-1 Not Available Humans URadixin Not Available Humans USpectrin beta chain, non-erythrocytic 1 Not Available Humans UInositol-trisphosphate 3-kinase A Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as inositol phosphates. These are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Alcohols and polyols
- Direct Parent
- Inositol phosphates
- Alternative Parents
- Monoalkyl phosphates / Cyclohexanols / Polyols / Organic oxides / Hydrocarbon derivatives
- Substituents
- Aliphatic homomonocyclic compound / Alkyl phosphate / Cyclohexanol / Hydrocarbon derivative / Inositol phosphate / Monoalkyl phosphate / Organic oxide / Organic phosphoric acid derivative / Phosphoric acid ester / Polyol
- Molecular Framework
- Aliphatic homomonocyclic compounds
- External Descriptors
- myo-inositol trisphosphate (CHEBI:16595)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- MU34XVK5NR
- CAS number
- 85166-31-0
- InChI Key
- MMWCIQZXVOZEGG-XJTPDSDZSA-N
- InChI
- 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
- IUPAC Name
- {[(1R,2S,3R,4R,5S,6R)-2,3,5-trihydroxy-4,6-bis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
- 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
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0001498
- KEGG Compound
- C01245
- PubChem Compound
- 439456
- PubChem Substance
- 46506346
- ChemSpider
- 388562
- BindingDB
- 50075183
- ChEBI
- 16595
- ChEMBL
- CHEMBL279107
- ZINC
- ZINC000004095598
- PDBe Ligand
- I3P
- PDB Entries
- 1btn / 1djx / 1gc6 / 1h0a / 1mai / 1n4k / 1nu2 / 1oqn / 1u29 / 1w2c … show 49 more
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 14.8 mg/mL ALOGPS logP -0.86 ALOGPS logP -4.2 Chemaxon logS -1.4 ALOGPS pKa (Strongest Acidic) 0.54 Chemaxon pKa (Strongest Basic) -3.7 Chemaxon Physiological Charge -6 Chemaxon Hydrogen Acceptor Count 12 Chemaxon Hydrogen Donor Count 9 Chemaxon Polar Surface Area 260.97 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 68.39 m3·mol-1 Chemaxon Polarizability 29.61 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-002b-7195200000-2871156f7c1e00704088 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0000900000-d2838b10b80df1958e70 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0000900000-6facbbd04abf785addf3 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0014900000-978ae3dbee5930e0e930 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-4000900000-81a715d650a5f2f3702f Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-9221000000-64ffdbd4f9caba4175e3 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-004j-9211100000-f919f6dafb0c302af557 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 188.8982656 predictedDarkChem Lite v0.1.0 [M-H]- 188.9820656 predictedDarkChem Lite v0.1.0 [M-H]- 155.63837 predictedDeepCCS 1.0 (2019) [M+H]+ 186.0366656 predictedDarkChem Lite v0.1.0 [M+H]+ 187.0210656 predictedDarkChem Lite v0.1.0 [M+H]+ 158.03548 predictedDeepCCS 1.0 (2019) [M+Na]+ 187.5501656 predictedDarkChem Lite v0.1.0 [M+Na]+ 185.7850656 predictedDarkChem Lite v0.1.0 [M+Na]+ 164.19228 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Inositol 1,4,5-trisphosphate-gated calcium channel that, upon inositol 1,4,5-trisphosphate binding, mediates calcium release from the endoplasmic reticulum (ER) (PubMed:10620513, PubMed:27108797). Undergoes conformational changes upon ligand binding, suggesting structural flexibility that allows the channel to switch from a closed state, capable of interacting with its ligands such as 1,4,5-trisphosphate and calcium, to an open state, capable of transferring calcium ions across the ER membrane (By similarity). Cytoplasmic calcium released from the ER triggers apoptosis by the activation of CAMK2 complex (By similarity). Involved in the regulation of epithelial secretion of electrolytes and fluid through the interaction with AHCYL1 (By similarity). Part of a complex composed of HSPA9, ITPR1 and VDAC1 that regulates mitochondrial calcium-dependent apoptosis by facilitating calcium transport from the ER lumen to the mitochondria intermembrane space thus providing calcium for the downstream calcium channel MCU that directly releases it into mitochondria matrix (By similarity). Regulates fertilization and egg activation by tuning the frequency and amplitude of calcium oscillations (By similarity)
- Specific Function
- ATP binding
- Gene Name
- ITPR1
- Uniprot ID
- Q14643
- Uniprot Name
- Inositol 1,4,5-trisphosphate-gated calcium channel ITPR1
- Molecular Weight
- 313926.375 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Inositol 1,4,5-trisphosphate-gated calcium channel that, upon 1D-myo-inositol 1,4,5-trisphosphate binding, transports calcium from the endoplasmic reticulum lumen to cytoplasm, thus releasing the intracellular calcium and therefore participates in cellular calcium ion homeostasis (PubMed:32949214, PubMed:37898605, PubMed:8081734, PubMed:8288584). 1D-myo-inositol 1,4,5-trisphosphate binds to the ligand-free channel without altering its global conformation, yielding the low-energy resting state, then progresses through resting-to preactivated transitions to the higher energy preactivated state, which increases affinity for calcium, promoting binding of the low basal cytosolic calcium at the juxtamembrane domain (JD) site, favoring the transition through the ensemble of high-energy intermediate states along the trajectory to the fully-open activated state (PubMed:30013099, PubMed:35301323, PubMed:37898605). Upon opening, releases calcium in the cytosol where it can bind to the low-affinity cytoplasmic domain (CD) site and stabilizes the inhibited state to terminate calcium release (PubMed:30013099, PubMed:35301323, PubMed:37898605)
- Specific Function
- calcium ion binding
- Gene Name
- ITPR3
- Uniprot ID
- Q14573
- Uniprot Name
- Inositol 1,4,5-trisphosphate-gated calcium channel ITPR3
- Molecular Weight
- 304103.96 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Inositol 1,4,5-trisphosphate-gated calcium channel that upon inositol 1,4,5-trisphosphate binding transports calcium from the endoplasmic reticulum lumen to cytoplasm (PubMed:25329695). Exists in two states; a long-lived closed state where the channel is essentially 'parked' with only very rare visits to an open state and that ligands facilitate the transition from the 'parked' state into a 'drive' mode represented by periods of bursting activity (By similarity)
- Specific Function
- ATP binding
- Gene Name
- ITPR2
- Uniprot ID
- Q14571
- Uniprot Name
- Inositol 1,4,5-trisphosphate-gated calcium channel ITPR2
- Molecular Weight
- 308061.11 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
4. DetailsCytohesin-2
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Acts as a guanine-nucleotide exchange factor (GEF). Promotes guanine-nucleotide exchange on ARF1, ARF3 and ARF6. Activates ARF factors through replacement of GDP with GTP (By similarity). The cell membrane form, in association with ARL4 proteins, recruits ARF6 to the plasma membrane (PubMed:17398095). Involved in neurite growth (By similarity)
- Specific Function
- guanyl-nucleotide exchange factor activity
- Gene Name
- CYTH2
- Uniprot ID
- Q99418
- Uniprot Name
- Cytohesin-2
- Molecular Weight
- 46545.725 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
5. DetailsEpsin-1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Binds to membranes enriched in phosphatidylinositol 4,5-bisphosphate (PtdIns(4,5)P2). Modifies membrane curvature and facilitates the formation of clathrin-coated invaginations (By similarity). Regulates receptor-mediated endocytosis (PubMed:10393179, PubMed:10557078)
- Specific Function
- clathrin binding
- Gene Name
- EPN1
- Uniprot ID
- Q9Y6I3
- Uniprot Name
- Epsin-1
- Molecular Weight
- 60292.655 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes (PubMed:9188725). Essential for trophoblast and placental development (By similarity). Binds phosphatidylinositol 4,5-bisphosphate (PubMed:7890667, PubMed:9188725)
- Specific Function
- calcium ion binding
- Gene Name
- PLCD1
- Uniprot ID
- P51178
- Uniprot Name
- 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-1
- Molecular Weight
- 85664.285 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
7. DetailsRadixin
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Probably plays a crucial role in the binding of the barbed end of actin filaments to the plasma membrane
- Specific Function
- actin binding
- Gene Name
- RDX
- Uniprot ID
- P35241
- Uniprot Name
- Radixin
- Molecular Weight
- 68563.48 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
8. DetailsSpectrin beta chain, non-erythrocytic 1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Fodrin, which seems to be involved in secretion, interacts with calmodulin in a calcium-dependent manner and is thus candidate for the calcium-dependent movement of the cytoskeleton at the membrane. Plays a critical role in central nervous system development and function
- Specific Function
- actin binding
- Gene Name
- SPTBN1
- Uniprot ID
- Q01082
- Uniprot Name
- Spectrin beta chain, non-erythrocytic 1
- Molecular Weight
- 274606.995 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
9. DetailsInositol-trisphosphate 3-kinase A
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Catalyzes the phosphorylation of 1D-myo-inositol 1,4,5-trisphosphate (InsP3) into 1D-myo-inositol 1,3,4,5-tetrakisphosphate and participates to the regulation of calcium homeostasis
- Specific Function
- ATP binding
- Gene Name
- ITPKA
- Uniprot ID
- P23677
- Uniprot Name
- Inositol-trisphosphate 3-kinase A
- Molecular Weight
- 51008.32 Da
References
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:22