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Showing Compound Phosphatidylinositol-3,4,5-trisphosphate (FDB023351)

Record Information
Version1.0
Creation date2011-09-21 00:28:31 UTC
Update date2018-05-29 01:52:59 UTC
Primary IDFDB023351
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.

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.

[HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Phosphatidylinositol-3,4,5-trisphosphoric acidGenerator
1,2-Diacyl-sn-glycero-3-phospho-(1'-myo-inositol-3',4',5'-bisphosphate)HMDB
1-Phosphatidyl-1D-myo-inositol 3,4,5-trisphosphateHMDB
1-Atidyl-1D-myo-inositol 3,4,5-trisateHMDB
1,2-Diacyl-sn-glycero-3-O-(1'-myo-inositol-3',4',5'-bisate)HMDB
Atidylinositol-3,4,5-trisateHMDB
Phosphatidylinositol-3,4,5-trisphosphatehmdb
Phosphatidylinositol-3,4,5-trisphosphic acidhmdb
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC12H24O22P4
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
InChI IdentifierInChI=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
Isomeric SMILESCC(=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
Average Molecular Weight644.2008
Monoisotopic Molecular Weight643.9709685
Classification
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
  • 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

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9221350000-b16be7ebadf266750598Spectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_2_16, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_2_17, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphatidylinositol-3,4,5-trisphosphate, TMS_2_18, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ika-9200563000-9a60ed0c3fcbf50167f32016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-9110533000-fc66e6a74addc319984e2016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w29-9204410000-ff2fba934c963beb20a62016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052f-9000213000-32b5b2c505d6a6a73bd72016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9001211000-a6daae7f68ecbcc9ba342016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f50c048414e579ad0a7e2016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000794000-d2b55615db3cd4aeead32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-005a-7000911000-7e41bb115a7c12f0d6e32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9100160000-a155ea0d71acc5294fb42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000092000-8e9c207b385bcdcbaa0c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1000291000-137cfeaa77a7642499fa2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-83fc05b0f4b5c6b391352021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC05981
Pubchem Compound ID6857406
Pubchem Substance IDNot Available
ChEBI ID16618
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04249
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID47125
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Phosphatidylserine synthase 1PTDSS1P48651
Phosphatidylserine synthase 2PTDSS2Q9BVG9
N-acetylglucosaminyl-phosphatidylinositol de-N-acetylasePIGLQ9Y2B2
Phosphatidylinositol N-acetylglucosaminyltransferase subunit QPIGQQ9BRB3
Phosphatidylinositol N-acetylglucosaminyltransferase subunit APIGAP37287
Phosphatidylinositol N-acetylglucosaminyltransferase subunit HPIGHQ14442
Phosphatidylinositol N-acetylglucosaminyltransferase subunit CPIGCQ92535
GPI mannosyltransferase 1PIGMQ9H3S5
Phosphatidylinositol-glycan biosynthesis class W proteinPIGWQ7Z7B1
Phosphatidylinositol-glycan biosynthesis class X proteinPIGXQ8TBF5
GPI mannosyltransferase 4PIGZQ86VD9
GPI mannosyltransferase 3PIGBQ92521
Phosphatidylinositol-glycan biosynthesis class F proteinPIGFQ07326
GPI ethanolamine phosphate transferase 2PIGGQ5H8A4
GPI ethanolamine phosphate transferase 1PIGNO95427
GPI ethanolamine phosphate transferase 3PIGOQ8TEQ8
GPI transamidase component PIG-SPIGSQ96S52
GPI transamidase component PIG-TPIGTQ969N2
Phosphatidylinositol glycan anchor biosynthesis class U proteinPIGUQ9H490
GPI mannosyltransferase 2PIGVQ9NUD9
Phosphatidylinositol N-acetylglucosaminyltransferase subunit YPIGYQ3MUY2
Phosphatidylserine decarboxylase proenzymePISDQ9UG56
Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2INPPL1O15357
Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 1INPP5DQ92835
Phosphatidylinositol 3,4,5-trisphosphate 3-phosphatase TPTE2TPTE2Q6XPS3
Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit delta isoformPIK3CDO00329
Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit beta isoformPIK3CBP42338
Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha isoformPIK3CAP42336
Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit gamma isoformPIK3CGP48736
Phospholipase A1 member APLA1AQ53H76
PI-PLC X domain-containing protein 2PLCXD2Q0VAA5
PI-PLC X domain-containing protein 1PLCXD1Q9NUJ7
PI-PLC X domain-containing protein 3PLCXD3Q63HM9
Pathways
NameSMPDB LinkKEGG Link
Inositol MetabolismSMP00011 map00562
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference