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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-09-18 19:38:39 UTC
HMDB IDHMDB0001143
Secondary Accession Numbers
  • HMDB01143
Metabolite Identification
Common NameInositol 1,3,4-trisphosphate
DescriptionInositol 1,3,4-trisphosphate (CAS: 98102-63-7), also known as Ins(1,3,4)P3 or I3S, 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. Within humans, inositol 1,3,4-trisphosphate participates in several enzymatic reactions. In particular, inositol 1,3,4-trisphosphate can be converted into 1D-myo-inositol 1,3,4,6-tetrakisphosphate through the action of the enzyme inositol-tetrakisphosphate 1-kinase. In addition, inositol 1,3,4-trisphosphate can be converted into inositol 1,3,4,5-tetraphosphate through its interaction with the enzyme inositol-tetrakisphosphate 1-kinase. In humans, inositol 1,3,4-trisphosphate is involved in inositol metabolism. Inositol 1,3,4-trisphosphate is a specific regulator of cellular signalling.
Structure
Data?1600457919
Synonyms
ValueSource
(1S,3S,4S)-1,3,4-TRIPHOSPHO-myo-inositolChEBI
D-Myo-inositol 1,3,4-trisphosphateChEBI
D-Myo-inositol 1,3,4-trisphosphoric acidGenerator
Inositol 1,3,4-trisphosphoric acidGenerator
1,3,4-ItpHMDB
1D-Myo-inositol 1,3,4-trisphosphateHMDB
I3SHMDB
Inositol 1,3,4-triphosphateHMDB
Myo-inositol 1,3,4-trisphosphateHMDB
Inositol 1,3,4-trisphosphate, (D)-isomerHMDB
D-myo-Inositol 1,3,4-tris(phosphate)HMDB
Inositol 1,3,4-trisphosphateHMDB
Ins(1,3,4)P3HMDB
Chemical FormulaC6H15O15P3
Average Molecular Weight420.0956
Monoisotopic Molecular Weight419.962379346
IUPAC Name{[(1S,2R,3R,4S,5S,6S)-2,3,5-trihydroxy-4,6-bis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional Nameinositol 1,3,4-trisphosphate
CAS Registry Number93133-76-7
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-MLQGYMEPSA-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
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
Polarizability29.73 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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, Positivesplash10-0fka-8912544000-6466de288b248e0534c9Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-0006-0091000000-4748b18c24a28a83e10bSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-00ba-9030000000-32edb6df84b89249800aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-0udi-0000900000-1b3fca9ae09a6e9974b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 13V, negativesplash10-0udi-0000900000-a276fc4491e761718dfaSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 16V, negativesplash10-0udi-0002900000-bcbe8de3f6c9f3878dc2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 21V, negativesplash10-0udi-1609700000-8524975955b3b52a5188Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 26V, negativesplash10-0pk9-4809100000-bd4057c77d97fcd8899cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 31V, negativesplash10-056r-9805000000-7df4af8b6064aead614dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 36V, negativesplash10-004i-9401000000-4c1e912ddb150b70b5d4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 43V, negativesplash10-004i-9200000000-84c539d19c53654b7250Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 50V, negativesplash10-004i-9100000000-588efa0963cb71999431Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 60V, negativesplash10-004i-9000000000-6a2554d172da41062dddSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-0udi-0109000000-0e68666378959fa09055Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-004i-9000000000-46d4cee1b5ac630ba9b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-0zfr-0890000000-107341de028331b689c2Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-004i-6900000000-dc0e986525b75ecb2fb0Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-08gi-0849000000-19971dee01d98c786cd0Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, negativesplash10-0a4i-0952000000-fd8d641519350c7213eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-014i-0000900000-d3ffebcbd2b7887c7769Spectrum
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
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01729
Phenol Explorer Compound IDNot Available
FooDB IDFDB022450
KNApSAcK IDNot Available
Chemspider ID388561
KEGG Compound IDC01243
BioCyc IDINOSITOL-1-3-4-TRIPHOSPHATE
BiGG ID37172
Wikipedia LinkNot Available
METLIN ID6035
PubChem Compound439455
PDB IDNot Available
ChEBI ID18228
Food Biomarker OntologyNot Available
VMH IDMI134P
References
Synthesis ReferenceMarecek J F; Estevez V A; Prestwich G D New tetherable derivatives of myo-inositol 2,4,5- and 1,3,4-trisphosphates. Carbohydrate research (1992), 234 65-73.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Major isoenzyme hydrolyzing the calcium-mobilizing second messenger Ins(1,4,5)P3, this is a signal-terminating reaction.
Gene Name:
INPP5A
Uniprot ID:
Q14642
Molecular weight:
47819.155
Reactions
myo-Inositol 1,3,4,5-tetrakisphosphate + Water → Inositol 1,3,4-trisphosphate + Phosphatedetails
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Not Available
Gene Name:
INPP1
Uniprot ID:
P49441
Molecular weight:
43997.62
Reactions
Inositol 1,3,4-trisphosphate + Water → D-myo-Inositol 3,4-bisphosphate + Phosphatedetails
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Inositol 5-phosphatase, which converts inositol 1,4,5-trisphosphate to inositol 1,4-bisphosphate. Also converts phosphatidylinositol 4,5-bisphosphate to phosphatidylinositol 4-phosphate and inositol 1,3,4,5-tetrakisphosphate to inositol 1,3,4-trisphosphate in vitro. May be involved in modulation of the function of inositol and phosphatidylinositol polyphosphate-binding proteins that are present at membranes ruffles (By similarity).
Gene Name:
INPP5J
Uniprot ID:
Q15735
Molecular weight:
70238.575
Reactions
myo-Inositol 1,3,4,5-tetrakisphosphate + Water → Inositol 1,3,4-trisphosphate + Phosphatedetails
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Inositol 5-phosphatase which acts on inositol 1,4,5-trisphosphate, inositol 1,3,4,5-tetrakisphosphate, phosphatidylinositol 4,5-bisphosphate and phosphatidylinositol 3,4,5-trisphosphate. Has 6-fold higher affinity for phosphatidylinositol 4,5-bisphosphate than for inositol 1,4,5-trisphosphate. May negatively regulate assembly of the actin cytoskeleton.
Gene Name:
INPP5K
Uniprot ID:
Q9BT40
Molecular weight:
42783.425
Reactions
myo-Inositol 1,3,4,5-tetrakisphosphate + Water → Inositol 1,3,4-trisphosphate + Phosphatedetails
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Phosphatidylinositol (PtdIns) phosphatase that specifically hydrolyzes the 5-phosphate of phosphatidylinositol-3,4,5-trisphosphate (PtdIns(3,4,5)P3) to produce PtdIns(3,4)P2, thereby negatively regulating the PI3K (phosphoinositide 3-kinase) pathways. Plays a central role in regulation of PI3K-dependent insulin signaling, although the precise molecular mechanisms and signaling pathways remain unclear. While overexpression reduces both insulin-stimulated MAP kinase and Akt activation, its absence does not affect insulin signaling or GLUT4 trafficking. Confers resistance to dietary obesity. May act by regulating AKT2, but not AKT1, phosphorylation at the plasma membrane. Part of a signaling pathway that regulates actin cytoskeleton remodeling. Required for the maintenance and dynamic remodeling of actin structures as well as in endocytosis, having a major impact on ligand-induced EGFR internalization and degradation. Participates in regulation of cortical and submembraneous actin by hydrolyzing PtdIns(3,4,5)P3 thereby regulating membrane ruffling. Regulates cell adhesion and cell spreading. Required for HGF-mediated lamellipodium formation, cell scattering and spreading. Acts as a negative regulator of EPHA2 receptor endocytosis by inhibiting via PI3K-dependent Rac1 activation. Acts as a regulator of neuritogenesis by regulating PtdIns(3,4,5)P3 level and is required to form an initial protrusive pattern, and later, maintain proper neurite outgrowth. Acts as a negative regulator of the FC-gamma-RIIA receptor (FCGR2A). Mediates signaling from the FC-gamma-RIIB receptor (FCGR2B), playing a central role in terminating signal transduction from activating immune/hematopoietic cell receptor systems. Involved in EGF signaling pathway. Upon stimulation by EGF, it is recruited by EGFR and dephosphorylates PtdIns(3,4,5)P3. Plays a negative role in regulating the PI3K-PKB pathway, possibly by inhibiting PKB activity. Down-regulates Fc-gamma-R-mediated phagocytosis in macrophages independently of INPP5D/SHIP1. In macrophages, down-regulates NF-kappa-B-dependent gene transcription by regulating macrophage colony-stimulating factor (M-CSF)-induced signaling. May also hydrolyze PtdIns(1,3,4,5)P4, and could thus affect the levels of the higher inositol polyphosphates like InsP6.
Gene Name:
INPPL1
Uniprot ID:
O15357
Molecular weight:
138597.495
General function:
Involved in catalytic activity
Specific function:
Kinase that can phosphorylate various inositol polyphosphate such as Ins(3,4,5,6)P4 or Ins(1,3,4)P3. Phosphorylates Ins(3,4,5,6)P4 at position 1 to form Ins(1,3,4,5,6)P5. This reaction is thought to have regulatory importance, since Ins(3,4,5,6)P4 is an inhibitor of plasma membrane Ca(2+)-activated Cl(-) channels, while Ins(1,3,4,5,6)P5 is not. Also phosphorylates Ins(1,3,4)P3 on O-5 and O-6 to form Ins(1,3,4,6)P4, an essential molecule in the hexakisphosphate (InsP6) pathway. Also acts as an inositol polyphosphate phosphatase that dephosphorylate Ins(1,3,4,5)P4 and Ins(1,3,4,6)P4 to Ins(1,3,4)P3, and Ins(1,3,4,5,6)P5 to Ins(3,4,5,6)P4. May also act as an isomerase that interconverts the inositol tetrakisphosphate isomers Ins(1,3,4,5)P4 and Ins(1,3,4,6)P4 in the presence of ADP and magnesium. Probably acts as the rate-limiting enzyme of the InsP6 pathway. Modifies TNF-alpha-induced apoptosis by interfering with the activation of TNFRSF1A-associated death domain.
Gene Name:
ITPK1
Uniprot ID:
Q13572
Molecular weight:
45620.645
Reactions
Adenosine triphosphate + Inositol 1,3,4-trisphosphate → ADP + myo-Inositol 1,3,4,5-tetrakisphosphatedetails
Adenosine triphosphate + Inositol 1,3,4-trisphosphate → ADP + D-myo-Inositol 1,3,4,6-tetrakisphosphatedetails