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Human Metabolome Database Version 3.5

Showing metabocard for PIP2(18:1(11Z)/18:3(9Z,12Z,15Z)) (HMDB10079)

• Identification
• Taxonomy
• Ontology
• Physical properties
• Spectra
• Biological properties
• Concentrations
• Links
• References

enzymes (80)

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Record Information
Version	3.5
Creation Date	2008-09-11 20:04:44 -0600
Update Date	2013-02-08 17:23:59 -0700
HMDB ID	HMDB10079
Secondary Accession Numbers	None
Metabolite Identification
Common Name	PIP2(18:1(11Z)/18:3(9Z,12Z,15Z))
Description	PIP2(18:1(11Z)/18:3(9Z,12Z,15Z)) is a phosphatidylinositol bisphosphate. Phosphatidylinositol bisphosphates are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to a bisphosphorylated inositol (hexahydroxycyclohexane). Phosphatidylinositol bisphosphates are generated from phosphatidylinositols which are 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. Phosphatidylinositols bisphosphates 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. PIP2(18:1(11Z)/18:3(9Z,12Z,15Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of a-linolenic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the a-linolenic acid moiety is derived from seed oils, especially canola and soybean oil. The most important phosphatidylinositol bisphosphate in both quantitative and biological terms is 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. Phosphatidylinositols phosphates are usually present at low levels only in tissues, typically at about 1 to 3% of the concentration of phosphatidylinositol.
Structure	Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure
Synonyms	1-(11Z-Octadecenoyl)-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycero-3-phospho-(1'-myo-inositol-3',4'-bisphosphate) 1-Phosphatidyl-D-myo-inositol 4,5-bisphosphate 1-Phosphatidyl-delta-myo-inositol 4,5-bisphosphate 1-Vaccenoyl-2-a-linolenoyl-sn-glycero-3-phosphoinositol-bisphosphate 1-Vaccenoyl-2-alpha-linolenoyl-sn-glycero-3-phosphoinositol-bisphosphate Phosphatidylinositol Diphosphate(18:1/18:3) Phosphatidylinositol Diphosphate(18:1n7/18:3n3) Phosphatidylinositol Diphosphate(18:1w7/18:3w3) Phosphatidylinositol Diphosphate(36:4) PIP2(18:1/18:3) PIP2(18:1n7/18:3n3) PIP2(18:1w7/18:3w3) PIP2(36:4) PIP2[3',4'](18:1(11Z)/18:3(9Z,12Z,15Z))
Chemical Formula	C45H81O19P3
Average Molecular Weight	1019.0345
Monoisotopic Molecular Weight	1018.458489946
IUPAC Name	{[(1S,3S)-2,4,5-trihydroxy-3-({hydroxy[(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphoryl}oxy)-6-(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional IUPAC Name	[(1S,3S)-2,4,5-trihydroxy-3-{[hydroxy(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxyphosphoryl]oxy}-6-(phosphonooxy)cyclohexyl]oxyphosphonic acid
CAS Registry Number	Not Available
SMILES	CCCCCC\C=C/CCCCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)O[C@H]1C(O)C(O)C(OP(=O)(O)O)[C@@H](OP(=O)(O)O)C1O)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC
InChI Identifier	InChI=1S/C45H81O19P3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(46)59-35-37(61-39(47)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)36-60-67(57,58)64-43-40(48)41(49)44(62-65(51,52)53)45(42(43)50)63-66(54,55)56/h6,8,12-15,18,20,37,40-45,48-50H,3-5,7,9-11,16-17,19,21-36H2,1-2H3,(H,57,58)(H2,51,52,53)(H2,54,55,56)/b8-6-,14-12-,15-13-,20-18-/t37-,40?,41?,42?,43+,44?,45+/m1/s1
InChI Key	PIHIKLUSFHLVID-BAXWWUBFSA-N
Chemical Taxonomy
Kingdom	Organic Compounds
Super Class	Lipids
Class	Glycerophospholipids
Sub Class	Glycerophosphoinositol Phosphates
Other Descriptors	Aliphatic Homomonocyclic Compounds
Substituents	1,2 Diol Carboxylic Acid Ester Cyclic Alcohol Cyclitol Derivative Cyclohexane Diacylglycerophosphoinositol Dicarboxylic Acid Derivative Fatty Acid Ester Inositol Phosphate Organic Hypophosphite Organic Phosphite Phosphoric Acid Ester Secondary Alcohol
Direct Parent	Phosphatidylinositol Phosphates
Ontology
Status	Expected and Not 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 0.044 g/L ALOGPS LogP 5.56 ALOGPS LogP 9.08 ChemAxon LogS -4.36 ALOGPS pKa (strongest acidic) 0.63 ChemAxon pKa (strongest basic) -3.7 ChemAxon Hydrogen Acceptor Count 13 ChemAxon Hydrogen Donor Count 8 ChemAxon Polar Surface Area 302.57 A2 ChemAxon Rotatable Bond Count 42 ChemAxon Refractivity 255.18 ChemAxon Polarizability 107.94 ChemAxon Formal Charge 0 ChemAxon Physiological Charge -5 ChemAxon
Spectra
	Not Available
Biological Properties
Cellular Locations	Extracellular Membrane
Biofluid Locations	Not Available
Tissue Location	All Tissues Brain
Pathways	Not Available
Normal Concentrations
	Not Available
Abnormal Concentrations
	Not Available
Associated Disorders and Diseases
Disease References	None
Associated OMIM IDs	None
External Links
DrugBank ID	Not Available
Phenol Explorer Compound ID	Not Available
Phenol Explorer Metabolite ID	Not Available
FoodDB ID	FDB027262
KNApSAcK ID	Not Available
Chemspider ID	24767956
KEGG Compound ID	C00626
BioCyc ID	Phosphatidylinositols
BiGG ID	Not Available
Wikipedia Link	Lecithin
NuGOwiki Link	HMDB10079
Metagene Link	HMDB10079
METLIN ID	Not Available
PubChem Compound	53480270
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
Name: 1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase beta-1 Reactions: Gene Name: PLCB1 Uniprot ID: Q9NQ66 Protein Sequence: FASTA Gene Sequence: FASTA
Name: 1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase beta-4 Reactions: Gene Name: PLCB4 Uniprot ID: Q15147 Protein Sequence: FASTA Gene Sequence: FASTA
Name: 1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase beta-2 Reactions: Gene Name: PLCB2 Uniprot ID: Q00722 Protein Sequence: FASTA Gene Sequence: FASTA
Name: 1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase beta-3 Reactions: Gene Name: PLCB3 Uniprot ID: Q01970 Protein Sequence: FASTA Gene Sequence: FASTA
Name: 1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase gamma-2 Reactions: Gene Name: PLCG2 Uniprot ID: P16885 Protein Sequence: FASTA Gene Sequence: FASTA
Name: 1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase gamma-1 Reactions: Gene Name: PLCG1 Uniprot ID: P19174 Protein Sequence: FASTA Gene Sequence: FASTA
Name: 1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase delta-1 Reactions: Gene Name: PLCD1 Uniprot ID: P51178 Protein Sequence: FASTA Gene Sequence: FASTA
Name: N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase Reactions: Gene Name: PIGL Uniprot ID: Q9Y2B2 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q Reactions: Gene Name: PIGQ Uniprot ID: Q9BRB3 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit A Reactions: Gene Name: PIGA Uniprot ID: P37287 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit H Reactions: Gene Name: PIGH Uniprot ID: Q14442 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit C Reactions: Gene Name: PIGC Uniprot ID: Q92535 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IG Reactions: Gene Name: ATP11C Uniprot ID: Q8NB49 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IH Reactions: Gene Name: ATP11A Uniprot ID: P98196 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit delta isoform Reactions: Gene Name: PIK3CD Uniprot ID: O00329 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase VA Reactions: Gene Name: ATP10A Uniprot ID: O60312 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IC Reactions: Gene Name: ATP8B1 Uniprot ID: O43520 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit beta isoform Reactions: Gene Name: PIK3CB Uniprot ID: P42338 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IIA Reactions: Gene Name: ATP9A Uniprot ID: O75110 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha isoform Reactions: Gene Name: PIK3CA Uniprot ID: P42336 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase VD Reactions: Gene Name: ATP10D Uniprot ID: Q9P241 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IB Reactions: Gene Name: ATP8A2 Uniprot ID: Q9NTI2 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IA Reactions: Gene Name: ATP8A1 Uniprot ID: Q9Y2Q0 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit gamma isoform Reactions: Gene Name: PIK3CG Uniprot ID: P48736 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IM Reactions: Gene Name: ATP8B4 Uniprot ID: Q8TF62 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IF Reactions: Gene Name: ATP11B Uniprot ID: Q9Y2G3 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase IK Reactions: Gene Name: ATP8B3 Uniprot ID: O60423 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol-3,4,5-trisphosphate 3-phosphatase and dual-specificity protein phosphatase PTEN Reactions: Gene Name: PTEN Uniprot ID: P60484 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol transfer protein beta isoform Reactions: Gene Name: PITPNB Uniprot ID: P48739 Protein Sequence: FASTA Gene Sequence: FASTA
Name: 1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase eta-2 Reactions: Gene Name: PLCH2 Uniprot ID: O75038 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipid scramblase 1 Reactions: Gene Name: PLSCR1 Uniprot ID: O15162 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylserine synthase 1 Reactions: Gene Name: PTDSS1 Uniprot ID: P48651 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylserine decarboxylase proenzyme Reactions: Gene Name: PISD Uniprot ID: Q9UG56 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol transfer protein alpha isoform Reactions: Gene Name: PITPNA Uniprot ID: Q00169 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipid transfer protein Reactions: Gene Name: PLTP Uniprot ID: P55058 Protein Sequence: FASTA Gene Sequence: FASTA
Name: GPI mannosyltransferase 1 Reactions: Gene Name: PIGM Uniprot ID: Q9H3S5 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylserine synthase 2 Reactions: Gene Name: PTDSS2 Uniprot ID: Q9BVG9 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol-glycan biosynthesis class W protein Reactions: Gene Name: PIGW Uniprot ID: Q7Z7B1 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol-glycan biosynthesis class X protein Reactions: Gene Name: PIGX Uniprot ID: Q8TBF5 Protein Sequence: FASTA Gene Sequence: FASTA
Name: GPI mannosyltransferase 4 Reactions: Gene Name: PIGZ Uniprot ID: Q86VD9 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol-3,4,5-trisphosphate 5-phosphatase 2 Reactions: Gene Name: INPPL1 Uniprot ID: O15357 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol-3,4,5-trisphosphate 5-phosphatase 1 Reactions: Gene Name: INPP5D Uniprot ID: Q92835 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol 3-kinase catalytic subunit type 3 Reactions: Gene Name: PIK3C3 Uniprot ID: Q8NEB9 Protein Sequence: FASTA Gene Sequence: FASTA
Name: PI-PLC X domain-containing protein 2 Reactions: Gene Name: PLCXD2 Uniprot ID: Q0VAA5 Protein Sequence: FASTA Gene Sequence: FASTA
Name: 1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase delta-4 Reactions: Gene Name: PLCD4 Uniprot ID: Q9BRC7 Protein Sequence: FASTA Gene Sequence: FASTA
Name: 1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase eta-1 Reactions: Gene Name: PLCH1 Uniprot ID: Q4KWH8 Protein Sequence: FASTA Gene Sequence: FASTA
Name: 1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase epsilon-1 Reactions: Gene Name: PLCE1 Uniprot ID: Q9P212 Protein Sequence: FASTA Gene Sequence: FASTA
Name: 1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase delta-3 Reactions: Gene Name: PLCD3 Uniprot ID: Q8N3E9 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipid scramblase 2 Reactions: Gene Name: PLSCR2 Uniprot ID: Q9NRY7 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipid scramblase 3 Reactions: Gene Name: PLSCR3 Uniprot ID: Q9NRY6 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipid scramblase 4 Reactions: Gene Name: PLSCR4 Uniprot ID: Q9NRQ2 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipid scramblase family member 5 Reactions: Gene Name: PLSCR5 Uniprot ID: A0PG75 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase VB Reactions: Gene Name: ATP10B Uniprot ID: O94823 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Probable phospholipid-transporting ATPase ID Reactions: Gene Name: ATP8B2 Uniprot ID: P98198 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phospholipase A1 member A Reactions: Gene Name: PLA1A Uniprot ID: Q53H76 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Serum deprivation-response protein Reactions: Gene Name: SDPR Uniprot ID: O95810 Protein Sequence: FASTA Gene Sequence: FASTA
Name: GPI mannosyltransferase 3 Reactions: Gene Name: PIGB Uniprot ID: Q92521 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol-glycan biosynthesis class F protein Reactions: Gene Name: PIGF Uniprot ID: Q07326 Protein Sequence: FASTA Gene Sequence: FASTA
Name: GPI ethanolamine phosphate transferase 2 Reactions: Gene Name: PIGG Uniprot ID: Q5H8A4 Protein Sequence: FASTA Gene Sequence: FASTA
Name: GPI ethanolamine phosphate transferase 1 Reactions: Gene Name: PIGN Uniprot ID: O95427 Protein Sequence: FASTA Gene Sequence: FASTA
Name: GPI ethanolamine phosphate transferase 3 Reactions: Gene Name: PIGO Uniprot ID: Q8TEQ8 Protein Sequence: FASTA Gene Sequence: FASTA
Name: GPI transamidase component PIG-S Reactions: Gene Name: PIGS Uniprot ID: Q96S52 Protein Sequence: FASTA Gene Sequence: FASTA
Name: GPI transamidase component PIG-T Reactions: Gene Name: PIGT Uniprot ID: Q969N2 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol glycan anchor biosynthesis class U protein Reactions: Gene Name: PIGU Uniprot ID: Q9H490 Protein Sequence: FASTA Gene Sequence: FASTA
Name: GPI mannosyltransferase 2 Reactions: Gene Name: PIGV Uniprot ID: Q9NUD9 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y Reactions: Gene Name: PIGY Uniprot ID: Q3MUY2 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Cytoplasmic phosphatidylinositol transfer protein 1 Reactions: Gene Name: PITPNC1 Uniprot ID: Q9UKF7 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Membrane-associated phosphatidylinositol transfer protein 1 Reactions: Gene Name: PITPNM1 Uniprot ID: O00562 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Membrane-associated phosphatidylinositol transfer protein 2 Reactions: Gene Name: PITPNM2 Uniprot ID: Q9BZ72 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Membrane-associated phosphatidylinositol transfer protein 3 Reactions: Gene Name: PITPNM3 Uniprot ID: Q9BZ71 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Pleckstrin homology domain-containing family A member 8 Reactions: Gene Name: PLEKHA8 Uniprot ID: Q96JA3 Protein Sequence: FASTA Gene Sequence: FASTA
Name: PI-PLC X domain-containing protein 1 Reactions: Gene Name: PLCXD1 Uniprot ID: Q9NUJ7 Protein Sequence: FASTA Gene Sequence: FASTA
Name: PI-PLC X domain-containing protein 3 Reactions: Gene Name: PLCXD3 Uniprot ID: Q63HM9 Protein Sequence: FASTA Gene Sequence: FASTA
Name: 1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase zeta-1 Reactions: Gene Name: PLCZ1 Uniprot ID: Q86YW0 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol 3,4,5-trisphosphate-dependent Rac exchanger 1 protein Reactions: Gene Name: PREX1 Uniprot ID: Q8TCU6 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Transmembrane protein 55A Reactions: Gene Name: TMEM55A Uniprot ID: Q8N4L2 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Transmembrane protein 55B Reactions: Gene Name: TMEM55B Uniprot ID: Q86T03 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol-3,4,5-trisphosphate 3-phosphatase TPTE2 Reactions: Gene Name: TPTE2 Uniprot ID: Q6XPS3 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Arf-GAP with coiled-coil, ANK repeat and PH domain-containing protein 1 Reactions: Gene Name: ACAP1 Uniprot ID: Q15027 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Arf-GAP with SH3 domain, ANK repeat and PH domain-containing protein 1 Reactions: Gene Name: ASAP1 Uniprot ID: Q9ULH1 Protein Sequence: FASTA Gene Sequence: FASTA

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