You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Bovine Metabolome Database.
Showing metabocard for Inositol 1,4,5-trisphosphate (BMDB0001498)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Version | 1.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2016-09-30 22:46:51 UTC | ||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2020-05-21 16:29:06 UTC | ||||||||||||||||||||||||||||||||||||||||||||||||||
BMDB ID | BMDB0001498 | ||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
| ||||||||||||||||||||||||||||||||||||||||||||||||||
Metabolite Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||
Common Name | Inositol 1,4,5-trisphosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Inositol 1,4,5-trisphosphate, also known as 1,4,5-insp3 or IP3, 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. Inositol 1,4,5-trisphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Inositol 1,4,5-trisphosphate exists in all eukaryotes, ranging from yeast to humans. | ||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms |
| ||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Formula | C6H15O15P3 | ||||||||||||||||||||||||||||||||||||||||||||||||||
Average Molecular Weight | 420.0956 | ||||||||||||||||||||||||||||||||||||||||||||||||||
Monoisotopic Molecular Weight | 419.962379346 | ||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional Name | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||
CAS Registry Number | 88269-39-0 | ||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||
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 | ||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key | MMWCIQZXVOZEGG-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. | ||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organic oxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Organooxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Alcohols and polyols | ||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Inositol phosphates | ||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
| ||||||||||||||||||||||||||||||||||||||||||||||||||
Molecular Framework | Aliphatic homomonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
| ||||||||||||||||||||||||||||||||||||||||||||||||||
Ontology | |||||||||||||||||||||||||||||||||||||||||||||||||||
Status | Expected but not Quantified | ||||||||||||||||||||||||||||||||||||||||||||||||||
Origin |
| ||||||||||||||||||||||||||||||||||||||||||||||||||
Biofunction | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||
Application | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular locations |
| ||||||||||||||||||||||||||||||||||||||||||||||||||
Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||
State | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties |
| ||||||||||||||||||||||||||||||||||||||||||||||||||
Predicted Properties | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra |
| ||||||||||||||||||||||||||||||||||||||||||||||||||
Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations |
| ||||||||||||||||||||||||||||||||||||||||||||||||||
Biospecimen Locations |
| ||||||||||||||||||||||||||||||||||||||||||||||||||
Pathways | |||||||||||||||||||||||||||||||||||||||||||||||||||
Normal Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||
| |||||||||||||||||||||||||||||||||||||||||||||||||||
Abnormal Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||
External Links | |||||||||||||||||||||||||||||||||||||||||||||||||||
HMDB ID | HMDB0001498 | ||||||||||||||||||||||||||||||||||||||||||||||||||
DrugBank ID | DB03401 | ||||||||||||||||||||||||||||||||||||||||||||||||||
Phenol Explorer Compound ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||
FooDB ID | FDB022657 | ||||||||||||||||||||||||||||||||||||||||||||||||||
KNApSAcK ID | C00007460 | ||||||||||||||||||||||||||||||||||||||||||||||||||
Chemspider ID | 388562 | ||||||||||||||||||||||||||||||||||||||||||||||||||
KEGG Compound ID | C01245 | ||||||||||||||||||||||||||||||||||||||||||||||||||
BioCyc ID | INOSITOL-1-4-5-TRISPHOSPHATE | ||||||||||||||||||||||||||||||||||||||||||||||||||
BiGG ID | 1485108 | ||||||||||||||||||||||||||||||||||||||||||||||||||
Wikipedia Link | Inositol trisphosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||
METLIN ID | 6282 | ||||||||||||||||||||||||||||||||||||||||||||||||||
PubChem Compound | 439456 | ||||||||||||||||||||||||||||||||||||||||||||||||||
PDB ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||
ChEBI ID | 16595 | ||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||
Synthesis Reference | 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. | ||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||
General References | Not Available |
Enzymes
- General function:
- Cell cycle control, cell division, chromosome partitioning
- Specific 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.
- Gene Name:
- PLCB1
- Uniprot ID:
- P10894
- Molecular weight:
- 138715.0
Reactions
phosphatidylinositol 4,5-bisphosphate + Water → 1,2-Diacyl-sn-glycerol + Inositol 1,4,5-trisphosphate | details |
- General function:
- Involved in calcium ion binding
- Specific function:
- Hydrolyzes the phosphatidylinositol 4,5-bisphosphate (PIP2) to generate 2 second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3). DAG mediates the activation of protein kinase C (PKC), while IP3 releases Ca(2+) from intracellular stores. Required for acrosome reaction in sperm during fertilization, probably by acting as an important enzyme for intracellular Ca(2+) mobilization in the zona pellucida-induced acrosome reaction. May play a role in cell growth. Modulates the liver regeneration in cooperation with nuclear PKC. Overexpression up-regulates the Erk signaling pathway and proliferation (By similarity).
- Gene Name:
- PLCD4
- Uniprot ID:
- P21671
- Molecular weight:
- 90581.0
- General function:
- Involved in calcium ion binding
- Specific 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. In vitro, hydrolyzes PtdIns(4,5)P2 in a Ca(2+)-dependent manner. Triggers intracellular Ca(2+) oscillations in oocytes solely during M phase and is involved in inducing oocyte activation and initiating embryonic development up to the blastocyst stage. Is therefore a strong candidate for the egg-activating soluble sperm factor that is transferred from the sperm into the egg cytoplasm following gamete membrane fusion. May exert an inhibitory effect on phospholipase-C-coupled processes that depend on calcium ions and protein kinase C, including CFTR trafficking and function.
- Gene Name:
- PLCZ1
- Uniprot ID:
- Q1RML2
- Molecular weight:
- 73732.0
- General function:
- Involved in calcium ion binding
- Specific 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. Essential for trophoblast and placental development.
- Gene Name:
- PLCD1
- Uniprot ID:
- P10895
- Molecular weight:
- 86073.0
- General function:
- Involved in calcium ion binding
- Specific function:
- Mediates the production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3). Plays an important role in the regulation of intracellular signaling cascades. Becomes activated in response to ligand-mediated activation of receptor-type tyrosine kinases, such as PDGFRA, PDGFRB, FGFR1, FGFR2, FGFR3 and FGFR4. Plays a role in actin reorganization and cell migration (By similarity).
- Gene Name:
- PLCG1
- Uniprot ID:
- P08487
- Molecular weight:
- 148313.0
- General function:
- Replication, recombination and repair
- Specific 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. This form has a role in retina signal transduction.
- Gene Name:
- PLCB4
- Uniprot ID:
- Q07722
- Molecular weight:
- 117110.0
- General function:
- Involved in actin binding
- Specific function:
- Myosins are actin-based motor molecules with ATPase activity. Unconventional myosins serve in intracellular movements. Their highly divergent tails are presumed to bind to membranous compartments, which would be moved relative to actin filaments. Involved in glucose transporter recycling in response to insulin by regulating movement of intracellular GLUT4-containing vesicles to the plasma membrane. Component of the hair cell's (the sensory cells of the inner ear) adaptation-motor complex. Acts as a mediator of adaptation of mechanoelectrical transduction in stereocilia of vestibular hair cells. Binds phosphoinositides and links the actin cytoskeleton to cellular membranes (By similarity).
- Gene Name:
- MYO1C
- Uniprot ID:
- Q27966
- Molecular weight:
- 121936.0
- General function:
- Involved in calcium ion binding
- Specific function:
- Receptor for inositol 1,4,5-trisphosphate, a second messenger that mediates the release of intracellular calcium (PubMed:11584008). This release is regulated by cAMP both dependently and independently of PKA (By similarity).
- Gene Name:
- ITPR2
- Uniprot ID:
- Q8WN96
- Molecular weight:
- 307820.0
- General function:
- Involved in G-protein coupled receptor protein signalin
- Specific function:
- Receptor for prostaglandin D2 (PGD2). The activity of this receptor is mainly mediated by G(s) proteins that stimulate adenylate cyclase, resulting in an elevation of intracellular cAMP. A mobilization of calcium is also observed, but without formation of inositol 1,4,5-trisphosphate (By similarity).
- Gene Name:
- PTGDR
- Uniprot ID:
- A5D7K8
- Molecular weight:
- 40372.0
- General function:
- Not Available
- Specific function:
- Component of the ERLIN1/ERLIN2 complex which mediates the endoplasmic reticulum-associated degradation (ERAD) of inositol 1,4,5-trisphosphate receptors (IP3Rs) such as ITPR1. Promotes sterol-accelerated ERAD of HMGCR probably implicating an AMFR/gp78-containing ubiquitin ligase complex. Involved in regulation of cellular cholesterol homeostasis by regulation the SREBP signaling pathway. May promote ER retention of the SCAP-SREBF complex (By similarity).
- Gene Name:
- ERLIN2
- Uniprot ID:
- Q1RMU4
- Molecular weight:
- 37730.0
- General function:
- Involved in calcium ion binding
- Specific function:
- Intracellular channel that mediates calcium release from the endoplasmic reticulum following stimulation by inositol 1,4,5-trisphosphate. Involved in the regulation of epithelial secretion of electrolytes and fluid through the interaction with AHCYL1 Plays a role in ER stress-induced apoptosis. Cytoplasmic calcium released from the ER triggers apoptosis by the activation of CaM kinase II, eventually leading to the activation of downstream apoptosis pathways.
- Gene Name:
- ITPR1
- Uniprot ID:
- Q9TU34
- Molecular weight:
- 308318.0
- General function:
- Involved in calcium ion binding
- Specific function:
- Receptor for inositol 1,4,5-trisphosphate, a second messenger that mediates the release of intracellular calcium.
- Gene Name:
- ITPR3
- Uniprot ID:
- Q8WN95
- Molecular weight:
- 303040.0
- General function:
- Not Available
- Specific function:
- Phosphatase that acts on various phosphoinositides, including phosphatidylinositol 4-phosphate, phosphatidylinositol (4,5)-bisphosphate and phosphatidylinositol (3,4,5)-trisphosphate. Has a role in clathrin-mediated endocytosis (By similarity). Hydrolyzes PIP2 bound to actin regulatory proteins resulting in the rearrangement of actin filaments downstream of tyrosine kinase and ASH/GRB2 (PubMed:9199318).
- Gene Name:
- SYNJ1
- Uniprot ID:
- O18964
- Molecular weight:
- 146584.0
Reactions
Inositol 1,4,5-trisphosphate + Water → 1D-Myo-inositol 1,4-bisphosphate + Hydrogen phosphate | details |