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Record Information
Version1.0
Creation Date2016-09-30 22:46:51 UTC
Update Date2020-05-21 16:29:06 UTC
BMDB IDBMDB0001498
Secondary Accession Numbers
  • BMDB01498
Metabolite Identification
Common NameInositol 1,4,5-trisphosphate
DescriptionInositol 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
Thumb
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 Weight420.0956
Monoisotopic Molecular Weight419.962379346
IUPAC Name{[(1R,2S,3R,4R,5S,6R)-2,3,5-trihydroxy-4,6-bis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional NameInsP3
CAS Registry Number88269-39-0
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
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 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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002b-7195200000-2871156f7c1e00704088View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0002-9052133000-5094b6ef55759c5a19ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-3008900000-e987cfb2603d94f1a6a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-2006900000-95047338604f8928313fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-4291000000-8e9bb388f01ec6d535abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-4001900000-395b5e207aa26dd43f27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9003200000-5e6369906fdedd08ad60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4b72b937fe3bf7fe817eView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Nucleus
Biospecimen Locations
  • Epidermis
  • Neuron
  • Pancreas
  • Platelet
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
NeuronExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PancreasExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
SpleenExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001498
DrugBank IDDB03401
Phenol Explorer Compound IDNot Available
FooDB IDFDB022657
KNApSAcK IDC00007460
Chemspider ID388562
KEGG Compound IDC01245
BioCyc IDINOSITOL-1-4-5-TRISPHOSPHATE
BiGG ID1485108
Wikipedia LinkInositol trisphosphate
METLIN ID6282
PubChem Compound439456
PDB IDNot Available
ChEBI ID16595
References
Synthesis ReferenceCooke, 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 ReferencesNot 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-trisphosphatedetails
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:
Not Available
Gene Name:
IPMK
Uniprot ID:
F1N1W2
Molecular weight:
47029.0
Reactions
2 Adenosine triphosphate + Inositol 1,4,5-trisphosphate →2 ADP + 1D-Myo-inositol 1,4,5,6-tetrakisphosphatedetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
MINPP1
Uniprot ID:
Q2TBT6
Molecular weight:
41435.0
Reactions
Inositol 1,3,4,5-tetraphosphate + Water → Inositol 1,4,5-trisphosphate + Hydrogen phosphatedetails
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 phosphatedetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
ITPKA
Uniprot ID:
A4FV33
Molecular weight:
50689.0
Reactions
Inositol 1,4,5-trisphosphate + Adenosine triphosphate → Inositol 1,3,4,5-tetraphosphate + ADPdetails