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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-12 01:59:42 UTC
Update Date2020-02-26 21:32:25 UTC
HMDB IDHMDB0009784
Secondary Accession Numbers
  • HMDB0062653
  • HMDB09784
  • HMDB62653
Metabolite Identification
Common NamePI(16:0/18:2(9Z,12Z))
DescriptionPI(16:0/18:2(9Z,12Z)) is a phosphatidylinositol. Phosphatidylinositols 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. PI(16:0/18:2(9Z,12Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the linoleic acid moiety is derived from seed oils. The inositol group that is part of every phosphatidylinositol lipid is covalently linked to the phosphate group that acts as a bridge to the lipid tail. In most organisms, the stereochemical form of this inositol is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial), although other forms can be found in certain plant phosphatidylinositols. Phosphatidylinositol is especially abundant in brain tissue, where it can amount to 10% of the phospholipids, but it is present in all tissues and cell types. There is usually less of it than of phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine. In animal tissues, phosphatidylinositol is the primary source of the arachidonic acid required for biosynthesis of eicosanoids, including prostaglandins, via the action of the enzyme phospholipase A2. 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
Data?1582752745
Synonyms
ValueSource
1-16:0-2-18:2-PhosphatidylinositolChEBI
1-Hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho-(1'-myo-inositol)ChEBI
1-Hexadecanoyl-2-linoleoyl-sn-glycero-3-phospho-D-myo-inositolChEBI
1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphoinositolChEBI
16:0-18:2-PIChEBI
Phosphatidylinositol(16:0/18:2)ChEBI
Phosphatidylinositol(16:0/18:2omega6)ChEBI
Phosphatidylinositol(34:2)ChEBI
PI(16:0/18:2(9Z,12Z))ChEBI
PI(16:0/18:2)ChEBI
PI(16:0/18:2omega6)ChEBI
PI(34:2)ChEBI
PIno(16:0/18:2)ChEBI
PIno(16:0/18:2omega6)ChEBI
PIno(34:2)ChEBI
1-Hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho-D-myo-inositolHMDB
1-Palmitoyl-2-linoleoyl-GPIHMDB
1-Palmitoyl-2-linoleoyl-glycero-3-phospho-(1'-myo-inositol)HMDB
1-Palmitoyl-2-linoleoyl-glycero-3-phospho-(1’-myo-inositol)HMDB
1-Palmitoyl-2-linoleoyl-sn-glycero-3-phospho-D-myo-inositolHMDB
GPI(16:0/18:2(9Z,12Z))HMDB
GPI(16:0/18:2)HMDB
GPI(16:0/18:2n6)HMDB
GPI(16:0/18:2w6)HMDB
GPI(34:2)HMDB
PI(16:0/18:2n6)HMDB
PI(16:0/18:2w6)HMDB
Phosphatidylinositol(16:0/18:2(9Z,12Z))HMDB
Phosphatidylinositol(16:0/18:2n6)HMDB
Phosphatidylinositol(16:0/18:2w6)HMDB
Chemical FormulaC43H79O13P
Average Molecular Weight835.066
Monoisotopic Molecular Weight834.525829602
IUPAC Name[(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]({[(1S,2R,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid
Traditional Name(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy([(1S,2R,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid
CAS Registry Number219584-66-4
SMILES
CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C43H79O13P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(45)55-35(34-54-57(51,52)56-43-41(49)39(47)38(46)40(48)42(43)50)33-53-36(44)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h11,13,17-18,35,38-43,46-50H,3-10,12,14-16,19-34H2,1-2H3,(H,51,52)/b13-11-,18-17-/t35-,38-,39-,40+,41-,42-,43-/m1/s1
InChI KeyBSNJSZUDOMPYIR-CUKLWHKZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-phosphatidyl-1d-myo-inositols. These are lipids containing a myo-inositol attached to the phosphate group of a glycerol-3-phosphate moiety, and two acyl chains linked to the glycerol at the O1- and O2- positions, through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoinositols
Direct Parent1-phosphatidyl-1D-myo-inositols
Alternative Parents
Substituents
  • 1-phosphatidyl-1d-myo-inositol
  • Inositol phosphate
  • Cyclohexanol
  • Fatty acid ester
  • Dialkyl phosphate
  • Cyclitol or derivatives
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
  • 1-hexadecanoyl-2-acyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:73212 )
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility0.001 g/LALOGPS
logP7.11ALOGPS
logP9.16ChemAxon
logS-5.9ALOGPS
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 Count38ChemAxon
Refractivity222 m³·mol⁻¹ChemAxon
Polarizability96.04 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • All Tissues
  • Brain
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.64 +/- 1.30 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID28639235
KEGG Compound IDNot Available
BioCyc IDCPD-8321
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID73212
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Majerus PW, Ross TS, Cunningham TW, Caldwell KK, Jefferson AB, Bansal VS: Recent insights in phosphatidylinositol signaling. Cell. 1990 Nov 2;63(3):459-65. [PubMed:2225061 ]
  2. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  7. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  8. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

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.