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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 15:16:34 UTC
Update Date2017-12-20 20:28:17 UTC
HMDB IDHMDB0004249
Secondary Accession Numbers
  • HMDB04249
Metabolite Identification
Common NamePhosphatidylinositol-3,4,5-trisphosphate
Description

Phosphatidylinositol (3,4,5)-trisphosphate (PtdIns(3,4,5)P3) commonly abbreviated to PIP3 is the product of the class I phosphoinositide 3-kinases (PI 3-kinases) activity on phosphatidylinositol (4,5)-bisphosphate. PtdIns(3,4,5)P3 is dephophosphorylated by the phosphatase, PTEN on the 3 position and by SHIPs (SH2-containing inositol phosphatase) on the 5' position of the inositol ring.

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The PH domain in a number of proteins binds to PtdIns(3,4,5)P3. Such proteins include Akt/PKB, PDK1, Btk1 and ARNO. The generation of PtdIns(3,4,5)P3 at the plasma membrane upon the activation of class I PI 3-kinases causes these proteins to translocate to the plasma membrane and accordingly affects their activity. The PH domain allows binding between PtdIns(3,4,5)P3 and G-protein coupled receptor kinases (GRKs). This enhances the binding of the GRK to the plasma membrane. (Wikipedia)

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Structure
Thumb
Synonyms
ValueSource
1,2-Diacyl-sn-glycero-3-phospho-(1'-myo-inositol-3',4',5'-bisphosphate)HMDB
1-Phosphatidyl-1D-myo-inositol 3,4,5-trisphosphateHMDB
Chemical FormulaC12H24O22P4
Average Molecular Weight644.2008
Monoisotopic Molecular Weight643.9709685
IUPAC Name{[(1S,2S,3S,4S,5R,6S)-3-({[2,2-bis(acetyloxy)ethoxy](hydroxy)phosphoryl}oxy)-2,4-dihydroxy-5,6-bis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional Name[(1S,2S,3S,4S,5R,6S)-3-{[2,2-bis(acetyloxy)ethoxy(hydroxy)phosphoryl]oxy}-2,4-dihydroxy-5,6-bis(phosphonooxy)cyclohexyl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CC(=O)OC(COP(O)(=O)O[C@@H]1[C@H](O)[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H]1O)OC(C)=O
InChI Identifier
InChI=1S/C12H24O22P4/c1-4(13)29-6(30-5(2)14)3-28-38(26,27)34-9-7(15)10(31-35(17,18)19)12(33-37(23,24)25)11(8(9)16)32-36(20,21)22/h6-12,15-16H,3H2,1-2H3,(H,26,27)(H2,17,18,19)(H2,20,21,22)(H2,23,24,25)/t7-,8-,9-,10+,11-,12-/m0/s1
InChI KeyRQQIRMLGKSPXSE-UQPICLANSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentInositol phosphates
Alternative Parents
Substituents
  • Inositol phosphate
  • Cyclohexanol
  • Acylal
  • Dialkyl phosphate
  • Monoalkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Carboxylic acid ester
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-7.965Not Available
Predicted Properties
PropertyValueSource
Water Solubility14.4 g/LALOGPS
logP-0.2ALOGPS
logP-4.1ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)0.38ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-7ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area349.1 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity109.37 m³·mol⁻¹ChemAxon
Polarizability47.51 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9221350000-b16be7ebadf266750598View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ika-9200563000-9a60ed0c3fcbf50167f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-9110533000-fc66e6a74addc319984eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w29-9204410000-ff2fba934c963beb20a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052f-9000213000-32b5b2c505d6a6a73bd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9001211000-a6daae7f68ecbcc9ba34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f50c048414e579ad0a7eView in MoNA
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 IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023351
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05981
BioCyc IDPHOSPHATIDYL-INOSITOL-345-TRISPHOSPHAT
BiGG ID47125
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID16618
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gurung R, Tan A, Ooms LM, McGrath MJ, Huysmans RD, Munday AD, Prescott M, Whisstock JC, Mitchell CA: Identification of a novel domain in two mammalian inositol-polyphosphate 5-phosphatases that mediates membrane ruffle localization. The inositol 5-phosphatase skip localizes to the endoplasmic reticulum and translocates to membrane ruffles following epidermal growth factor stimulation. J Biol Chem. 2003 Mar 28;278(13):11376-85. Epub 2003 Jan 20. [PubMed:12536145 ]
  2. Liu Q, Dumont DJ: Molecular cloning and chromosomal localization in human and mouse of the SH2-containing inositol phosphatase, INPP5D (SHIP). Amgen EST Program. Genomics. 1997 Jan 1;39(1):109-12. [PubMed:9027494 ]
  3. Ijuin T, Takenawa T: SKIP negatively regulates insulin-induced GLUT4 translocation and membrane ruffle formation. Mol Cell Biol. 2003 Feb;23(4):1209-20. [PubMed:12556481 ]
  4. Radu A, Neubauer V, Akagi T, Hanafusa H, Georgescu MM: PTEN induces cell cycle arrest by decreasing the level and nuclear localization of cyclin D1. Mol Cell Biol. 2003 Sep;23(17):6139-49. [PubMed:12917336 ]
  5. Maxwell MJ, Yuan Y, Anderson KE, Hibbs ML, Salem HH, Jackson SP: SHIP1 and Lyn Kinase Negatively Regulate Integrin alpha IIb beta 3 signaling in platelets. J Biol Chem. 2004 Jul 30;279(31):32196-204. Epub 2004 May 27. [PubMed:15166241 ]

Only showing the first 10 proteins. There are 80 proteins in total.

Enzymes

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.
Gene Name:
PLCB1
Uniprot ID:
Q9NQ66
Molecular weight:
138565.805
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. This form has a role in retina signal transduction.
Gene Name:
PLCB4
Uniprot ID:
Q15147
Molecular weight:
136105.065
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.
Gene Name:
PLCB2
Uniprot ID:
Q00722
Molecular weight:
134023.21
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.
Gene Name:
PLCB3
Uniprot ID:
Q01970
Molecular weight:
138797.725
General function:
Involved in phosphoinositide phospholipase C activity
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. It is a crucial enzyme in transmembrane signaling.
Gene Name:
PLCG2
Uniprot ID:
P16885
Molecular weight:
147868.67
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.
Gene Name:
PLCG1
Uniprot ID:
P19174
Molecular weight:
148658.92
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:
P51178
Molecular weight:
88134.23
General function:
Involved in N-acetylglucosaminylphosphatidylinositol de
Specific function:
Involved in the second step of GPI biosynthesis. De-N-acetylation of N-acetylglucosaminyl-phosphatidylinositol.
Gene Name:
PIGL
Uniprot ID:
Q9Y2B2
Molecular weight:
28530.965
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltransferase activity
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGQ
Uniprot ID:
Q9BRB3
Molecular weight:
65343.25
General function:
Involved in biosynthetic process
Specific function:
Necessary for the synthesis of N-acetylglucosaminyl-phosphatidylinositol, the very early intermediate in GPI-anchor biosynthesis.
Gene Name:
PIGA
Uniprot ID:
P37287
Molecular weight:
54126.065

Only showing the first 10 proteins. There are 80 proteins in total.