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Identification
YMDB IDYMDB00230
Name1-Phosphatidyl-D-myo-inositol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPhosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. In most organisms, the stereochemical form of the last is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PIs contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol.
Structure
Thumb
Synonyms
  • (3-Phosphatidyl)-1-D-inositol
  • 1-Phosphatidyl-1D-myo-inositol
  • 1-Phosphatidyl-myo-inositol
  • 1,2-Diacyl-sn-glycero-3-phosphoinositol
  • Phosphatidyl-1D-myo-inositol
  • Phosphatidylinositol
  • Phosphoinositides
  • Inositol phospholipids
  • Phosphatidylinositols
  • Phospholipids, inositide
  • PtdIns
  • Inositide phospholipids
  • Inositol, phosphatidyl
  • Phosphoglycerides, inositol
  • Phospholipids, inositol
  • Inositol phosphoglycerides
  • Phosphatidyl inositol
CAS numberNot Available
WeightAverage: 390.2345
Monoisotopic: 390.056327206
InChI KeyGUBXYMKIJFOYOA-WSRCIYAPSA-N
InChIInChI=1S/C11H19O13P/c12-3-21-1-5(22-4-13)2-23-25(19,20)24-11-9(17)7(15)6(14)8(16)10(11)18/h3-11,14-18H,1-2H2,(H,19,20)/t5?,6?,7-,8?,9+,10-,11?/m0/s1
IUPAC Name[2,3-bis(formyloxy)propoxy]({[(2R,3S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid
Traditional IUPAC Name2,3-bis(formyloxy)propoxy[(2R,3S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphinic acid
Chemical FormulaC11H19O13P
SMILES[H]OC1([H])C([H])(O[H])[C@]([H])(O[H])C([H])(OP(=O)(O[H])OC([H])([H])C([H])(OC([H])=O)C([H])([H])OC([H])=O)[C@]([H])(O[H])[C@@]1([H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylinositols. These are glycerophosphoinositols where the glycerol is esterified with two fatty acids.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoinositols
Direct ParentPhosphatidylinositols
Alternative Parents
Substituents
  • Diacylglycerophosphoinositol
  • Inositol phosphate
  • Cyclohexanol
  • Dialkyl phosphate
  • Cyclitol or derivatives
  • Alkyl phosphate
  • Dicarboxylic acid or derivatives
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Cyclic alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility27 g/LALOGPS
logP-1.7ALOGPS
logP-4.1ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.83ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area209.51 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity72.71 m³·mol⁻¹ChemAxon
Polarizability32.85 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cell envelope
  • mitochondrion
  • Golgi
  • endoplasmic reticulum
  • nucleus
  • vacuole
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
Inositol MetabolismPW002498 ThumbThumb?image type=greyscaleThumb?image type=simple
Inositol phosphate metabolismPW002495 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerophospholipid metabolismec00564 Map00564
Glycosylphosphatidylinositol(GPI)-anchor biosynthesisec00563 Map00563
Inositol phosphate metabolismec00562 Map00562
SMPDB Reactions
1-Phosphatidyl-D-myo-inositol + Adenosine triphosphate1-phosphatidyl-1D-myo-inositol 4-phosphate + ADP
1-Phosphatidyl-D-myo-inositol + Adenosine triphosphate1-Phosphatidyl-1D-myo-inositol 3-phosphate + ADP
KEGG Reactions
1-phosphatidyl-1D-myo-inositol 3-phosphate + waterphosphate + 1-Phosphatidyl-D-myo-inositol + hydron
Adenosine triphosphate + 1-Phosphatidyl-D-myo-inositol + hydron ↔ 1-phosphatidyl-1D-myo-inositol 4-phosphate + ADP
Adenosine triphosphate + 1-Phosphatidyl-D-myo-inositol + hydron → 1-phosphatidyl-1D-myo-inositol 4-phosphate + ADP
1-phosphatidyl-1D-myo-inositol 4-phosphate + waterphosphate + 1-Phosphatidyl-D-myo-inositol + hydron
Myoinositol + CDP-diacylglycerol → Cytidine monophosphate + 1-Phosphatidyl-D-myo-inositol + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-03y1-1352149000-d88efb76f7886b51159aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0005-2429000000-eb25eae6f367048dab43JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001d-9786000000-ef9de9b6628c1ae3f1d0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000b-8900000000-b353f13d30710ab1440fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-3039000000-ebc2bd0d92a4b2183e67JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-9263000000-6deaf9eca5534628df3cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9110000000-46ead7f49d30ae57b126JSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Foti, M., Audhya, A., Emr, S. D. (2001). "Sac1 lipid phosphatase and Stt4 phosphatidylinositol 4-kinase regulate a pool of phosphatidylinositol 4-phosphate that functions in the control of the actin cytoskeleton and vacuole morphology." Mol Biol Cell 12:2396-2411.11514624
  • Han, G. S., Audhya, A., Markley, D. J., Emr, S. D., Carman, G. M. (2002). "The Saccharomyces cerevisiae LSB6 gene encodes phosphatidylinositol 4-kinase activity." J Biol Chem 277:47709-47718.12361950
  • Taylor, G. S., Maehama, T., Dixon, J. E. (2000). "Myotubularin, a protein tyrosine phosphatase mutated in myotubular myopathy, dephosphorylates the lipid second messenger, phosphatidylinositol 3-phosphate." Proc Natl Acad Sci U S A 97:8910-8915.10900271
  • Nikawa, J., Yamashita, S. (1997). "Phosphatidylinositol synthase from yeast." Biochim Biophys Acta 1348:173-178.9370330
  • Strahl, T., Thorner, J. (2007). "Synthesis and function of membrane phosphoinositides in budding yeast, Saccharomyces cerevisiae." Biochim Biophys Acta 1771:353-404.17382260
  • Guo, S., Stolz, L. E., Lemrow, S. M., York, J. D. (1999). "SAC1-like domains of yeast SAC1, INP52, and INP53 and of human synaptojanin encode polyphosphoinositide phosphatases." J Biol Chem 274:12990-12995.10224048
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16749
HMDB IDHMDB06953
Pubchem Compound ID25245335
Kegg IDC01194
ChemSpider IDNot Available
FOODB IDFDB024159
Wikipedia IDNot Available
BioCyc ID1-PHOSPHATIDYL-MYO-INOSITOL

Enzymes

General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
May play a role in endocytic and/or exocytic pathways
Gene Name:
LSB6
Uniprot ID:
P42951
Molecular weight:
70216.39844
Reactions
ATP + 1-phosphatidyl-1D-myo-inositol → ADP + 1-phosphatidyl-1D-myo-inositol 4-phosphate.
General function:
Involved in binding
Specific function:
Acts on phosphatidylinositol (PI) in the first committed step in the production of the second messenger inositol-1,4,5,- trisphosphate. STT4 functions in PKC1 protein kinase pathway
Gene Name:
STT4
Uniprot ID:
P37297
Molecular weight:
214605.0
Reactions
ATP + 1-phosphatidyl-1D-myo-inositol → ADP + 1-phosphatidyl-1D-myo-inositol 4-phosphate.
General function:
Involved in binding
Specific function:
Phosphatidylinositol 3-kinase required for cytoplasm to vacuole transport (Cvt) and autophagy as a part of the autophagy- specific VPS34 PI3-kinase complex I. This complex is essential to recruit the ATG8-phosphatidylinositol conjugate and the ATG12-ATG5 conjugate to the pre-autophagosomal structure. Also involved in endosome-to-Golgi retrograde transport as part of the VPS34 PI3- kinase complex II. This second complex is required for the endosome-to-Golgi retrieval of PEP1 and KEX2, and the recruitment of VPS5 and VPS7, two components of the retromer complex, to endosomal membranes (probably through the synthesis of a specific pool of phosphatidylinositol 3-phosphate recruiting the retromer to the endosomes). Its activation by VPS15 may lead to the phosphorylation of phosphatidylinositol in the sorting compartment membrane. Finally, it might also be involved in ethanol tolerance and cell wall integrity
Gene Name:
VPS34
Uniprot ID:
P22543
Molecular weight:
100920.0
Reactions
ATP + 1-phosphatidyl-1D-myo-inositol → ADP + 1-phosphatidyl-1D-myo-inositol 3-phosphate.
General function:
Involved in binding
Specific function:
Acts on phosphatidylinositol (PI) in the first committed step in the production of the second messenger inositol-1,4,5,- trisphosphate. PIK1 is part of a nuclear phosphoinositide cycle and could control cytokinesis through the actin cytoskeleton
Gene Name:
PIK1
Uniprot ID:
P39104
Molecular weight:
119922.0
Reactions
ATP + 1-phosphatidyl-1D-myo-inositol → ADP + 1-phosphatidyl-1D-myo-inositol 4-phosphate.
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
CDP-diacylglycerol + myo-inositol = CMP + phosphatidyl-1D-myo-inositol
Gene Name:
PIS1
Uniprot ID:
P06197
Molecular weight:
24823.5
Reactions
CDP-diacylglycerol + myo-inositol → CMP + phosphatidyl-1D-myo-inositol.
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltr
Specific function:
Part of the complex catalyzing the transfer of N- acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis. Involved in cell wall biosynthesis
Gene Name:
GPI19
Uniprot ID:
Q04082
Molecular weight:
16089.40039
Reactions
UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol → UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol.
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:
GPI1
Uniprot ID:
P53306
Molecular weight:
70353.70313
Reactions
UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol → UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol.
General function:
Involved in biosynthetic process
Specific function:
Catalytic subunit in the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis
Gene Name:
SPT14
Uniprot ID:
P32363
Molecular weight:
51241.80078
Reactions
UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol → UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol.
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:
GPI2
Uniprot ID:
P46961
Molecular weight:
32576.80078
Reactions
UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol → UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol.
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:
GPI15
Uniprot ID:
P53961
Molecular weight:
26816.5
Reactions
UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol → UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol.
General function:
vacuole inheritance
Specific function:
Serine/threonine-protein kinase required for cytoplasm to vacuole transport (Cvt) and autophagy as a part of the autophagy-specific VPS34 PI3-kinase complex I. This complex is essential to recruit the ATG8-phosphatidylinositol conjugate and the ATG12-ATG5 conjugate to the pre-autophagosomal structure. Is also involved in endosome-to-Golgi retrograde transport as part of the VPS34 PI3-kinase complex II. This second complex is required for the endosome-to-Golgi retrieval of PEP1 and KEX2, and the recruitment of VPS5 and VPS7, two components of the retromer complex, to endosomal membranes (probably through the synthesis of a specific pool of phosphatidylinositol 3-phosphate recruiting the retromer to the endosomes). By regulating VPS34 kinase activity, VPS15 appears to be essential for the efficient delivery of soluble hydrolases to the yeast vacuole.
Gene Name:
VPS15
Uniprot ID:
P22219
Molecular weight:
166370.295
Reactions

Transporters

General function:
vacuole inheritance
Specific function:
Serine/threonine-protein kinase required for cytoplasm to vacuole transport (Cvt) and autophagy as a part of the autophagy-specific VPS34 PI3-kinase complex I. This complex is essential to recruit the ATG8-phosphatidylinositol conjugate and the ATG12-ATG5 conjugate to the pre-autophagosomal structure. Is also involved in endosome-to-Golgi retrograde transport as part of the VPS34 PI3-kinase complex II. This second complex is required for the endosome-to-Golgi retrieval of PEP1 and KEX2, and the recruitment of VPS5 and VPS7, two components of the retromer complex, to endosomal membranes (probably through the synthesis of a specific pool of phosphatidylinositol 3-phosphate recruiting the retromer to the endosomes). By regulating VPS34 kinase activity, VPS15 appears to be essential for the efficient delivery of soluble hydrolases to the yeast vacuole.
Gene Name:
VPS15
Uniprot ID:
P22219
Molecular weight:
166370.295
Reactions
General function:
retrograde transport, endosome to Golgi
Specific function:
Required for cytoplasm to vacuole transport (Cvt), autophagy, nucleophagy, and mitophagy, as a part of the autophagy-specific VPS34 PI3-kinase complex I. This complex is essential to recruit the ATG8-phosphatidylinositol conjugate and the ATG12-ATG5 conjugate to the pre-autophagosomal structure. Also involved in endosome-to-Golgi retrograde transport as part of the VPS34 PI3-kinase complex II. This second complex is required for the endosome-to-Golgi retrieval of PEP1 and KEX2, and the recruitment of VPS5 and VPS7, two components of the retromer complex, to endosomal membranes (probably through the synthesis of a specific pool of phosphatidylinositol 3-phosphate recruiting the retromer to the endosomes). Plays also a role in regulation of filamentous growth.
Gene Name:
VPS30
Uniprot ID:
Q02948
Molecular weight:
63260.22
Reactions