Human Metabolome Database Version 3.5

Showing metabocard for PI(16:0/18:2(9Z,12Z)) (HMDB09784)

Record Information
Version 3.5
Creation Date 2008-09-11 19:59:42 -0600
Update Date 2013-02-08 17:23:15 -0700
HMDB ID HMDB09784
Secondary Accession Numbers None
Metabolite Identification
Common Name PI(16:0/18:2(9Z,12Z))
Description PI(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. 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 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 Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-Hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho-(1'-myo-inositol)
  2. 1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphoinositol
  3. Phosphatidylinositol(16:0/18:2)
  4. Phosphatidylinositol(16:0/18:2n6)
  5. Phosphatidylinositol(16:0/18:2w6)
  6. Phosphatidylinositol(34:2)
  7. PI(16:0/18:2)
  8. PI(16:0/18:2n6)
  9. PI(16:0/18:2w6)
  10. PI(34:2)
  11. PIno(16:0/18:2)
  12. PIno(16:0/18:2n6)
  13. PIno(16:0/18:2w6)
  14. PIno(34:2)
Chemical Formula C43H79O13P
Average Molecular Weight 835.0533
Monoisotopic Molecular Weight 834.525829126
IUPAC Name [(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]({[(1s,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid
Traditional IUPAC Name (2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy[(1s,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphinic acid
CAS Registry Number Not Available
SMILES CCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](O)C1O)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 Key BSNJSZUDOMPYIR-KOHXHNRGSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Glycerophospholipids
Sub Class Glycerophosphoinositols
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
Substituents
  • 1,2 Diol
  • Carboxylic Acid Ester
  • Cyclic Alcohol
  • Cyclitol Derivative
  • Cyclohexane
  • Dicarboxylic Acid Derivative
  • Fatty Acid Ester
  • Inositol Phosphate
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
  • Secondary Alcohol
Direct Parent Phosphatidylinositols
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Energy source
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.001 g/L ALOGPS
LogP 7.11 ALOGPS
LogP 9.16 ChemAxon
LogS -5.92 ALOGPS
pKa (strongest acidic) 1.83 ChemAxon
pKa (strongest basic) -3.6 ChemAxon
Hydrogen Acceptor Count 9 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 209.51 A2 ChemAxon
Rotatable Bond Count 38 ChemAxon
Refractivity 222 ChemAxon
Polarizability 96.29 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • All Tissues
  • Brain
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
2.64 +/- 1.30 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB026974
KNApSAcK ID Not Available
Chemspider ID 24767669 Link_out
KEGG Compound ID C00626 Link_out
BioCyc ID Phosphatidylinositols Link_out
BiGG ID Not Available
Wikipedia Link Lecithin Link_out
NuGOwiki Link HMDB09784 Link_out
Metagene Link HMDB09784 Link_out
METLIN ID Not Available
PubChem Compound Not Available
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes

Show all enzymes and transporters Important Only showing the first 50 enzymes. There are 80 enzymes in total.

Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-1
Reactions: Not Available
Gene Name: PLCB1
Uniprot ID: Q9NQ66 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-4
Reactions: Not Available
Gene Name: PLCB4
Uniprot ID: Q15147 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-2
Reactions: Not Available
Gene Name: PLCB2
Uniprot ID: Q00722 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-3
Reactions: Not Available
Gene Name: PLCB3
Uniprot ID: Q01970 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-2
Reactions: Not Available
Gene Name: PLCG2
Uniprot ID: P16885 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1
Reactions: Not Available
Gene Name: PLCG1
Uniprot ID: P19174 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-1
Reactions: Not Available
Gene Name: PLCD1
Uniprot ID: P51178 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase
Reactions: Not Available
Gene Name: PIGL
Uniprot ID: Q9Y2B2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q
Reactions: Not Available
Gene Name: PIGQ
Uniprot ID: Q9BRB3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit A
Reactions: Not Available
Gene Name: PIGA
Uniprot ID: P37287 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit H
Reactions: Not Available
Gene Name: PIGH
Uniprot ID: Q14442 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit C
Reactions: Not Available
Gene Name: PIGC
Uniprot ID: Q92535 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IG
Reactions: Not Available
Gene Name: ATP11C
Uniprot ID: Q8NB49 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IH
Reactions: Not Available
Gene Name: ATP11A
Uniprot ID: P98196 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit delta isoform
Reactions: Not Available
Gene Name: PIK3CD
Uniprot ID: O00329 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase VA
Reactions: Not Available
Gene Name: ATP10A
Uniprot ID: O60312 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IC
Reactions: Not Available
Gene Name: ATP8B1
Uniprot ID: O43520 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit beta isoform
Reactions: Not Available
Gene Name: PIK3CB
Uniprot ID: P42338 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IIA
Reactions: Not Available
Gene Name: ATP9A
Uniprot ID: O75110 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
Reactions: Not Available
Gene Name: PIK3CA
Uniprot ID: P42336 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase VD
Reactions: Not Available
Gene Name: ATP10D
Uniprot ID: Q9P241 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IB
Reactions: Not Available
Gene Name: ATP8A2
Uniprot ID: Q9NTI2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IA
Reactions: Not Available
Gene Name: ATP8A1
Uniprot ID: Q9Y2Q0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit gamma isoform
Reactions: Not Available
Gene Name: PIK3CG
Uniprot ID: P48736 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IM
Reactions: Not Available
Gene Name: ATP8B4
Uniprot ID: Q8TF62 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IF
Reactions: Not Available
Gene Name: ATP11B
Uniprot ID: Q9Y2G3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IK
Reactions: Not Available
Gene Name: ATP8B3
Uniprot ID: O60423 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol 3,4,5-trisphosphate 3-phosphatase and dual-specificity protein phosphatase PTEN
Reactions: Not Available
Gene Name: PTEN
Uniprot ID: P60484 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol transfer protein beta isoform
Reactions: Not Available
Gene Name: PITPNB
Uniprot ID: P48739 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase eta-2
Reactions: Not Available
Gene Name: PLCH2
Uniprot ID: O75038 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipid scramblase 1
Reactions: Not Available
Gene Name: PLSCR1
Uniprot ID: O15162 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylserine synthase 1
Reactions: Not Available
Gene Name: PTDSS1
Uniprot ID: P48651 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylserine decarboxylase proenzyme
Reactions: Not Available
Gene Name: PISD
Uniprot ID: Q9UG56 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol transfer protein alpha isoform
Reactions: Not Available
Gene Name: PITPNA
Uniprot ID: Q00169 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipid transfer protein
Reactions: Not Available
Gene Name: PLTP
Uniprot ID: P55058 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI mannosyltransferase 1
Reactions: Not Available
Gene Name: PIGM
Uniprot ID: Q9H3S5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylserine synthase 2
Reactions: Not Available
Gene Name: PTDSS2
Uniprot ID: Q9BVG9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol-glycan biosynthesis class W protein
Reactions: Not Available
Gene Name: PIGW
Uniprot ID: Q7Z7B1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol-glycan biosynthesis class X protein
Reactions: Not Available
Gene Name: PIGX
Uniprot ID: Q8TBF5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI mannosyltransferase 4
Reactions: Not Available
Gene Name: PIGZ
Uniprot ID: Q86VD9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2
Reactions: Not Available
Gene Name: INPPL1
Uniprot ID: O15357 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 1
Reactions: Not Available
Gene Name: INPP5D
Uniprot ID: Q92835 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol 3-kinase catalytic subunit type 3
Reactions: Not Available
Gene Name: PIK3C3
Uniprot ID: Q8NEB9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: PI-PLC X domain-containing protein 2
Reactions: Not Available
Gene Name: PLCXD2
Uniprot ID: Q0VAA5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-4
Reactions: Not Available
Gene Name: PLCD4
Uniprot ID: Q9BRC7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase eta-1
Reactions: Not Available
Gene Name: PLCH1
Uniprot ID: Q4KWH8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase epsilon-1
Reactions: Not Available
Gene Name: PLCE1
Uniprot ID: Q9P212 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-3
Reactions: Not Available
Gene Name: PLCD3
Uniprot ID: Q8N3E9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipid scramblase 2
Reactions: Not Available
Gene Name: PLSCR2
Uniprot ID: Q9NRY7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipid scramblase 3
Reactions: Not Available
Gene Name: PLSCR3
Uniprot ID: Q9NRY6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA