ChemFOnt: Showing chemical card for PIP2(18:1(11Z)/18:3(6Z,9Z,12Z)) (CFc000006117)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:52:01 UTC

Chemfont ID

CFc000006117

Molecule Identification

Common Name

PIP2(18:1(11Z)/18:3(6Z,9Z,12Z))

Definition

PIP2(18:1(11Z)/18:3(6Z,9Z,12Z)) 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(6Z,9Z,12Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of g-linolenic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the g-linolenic acid moiety is derived from animal fats. 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

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₄₅H₈₁O₁₉P₃

Average Molecular Weight

1019.0345

Monoisotopic Molecular Weight

1018.458489946

IUPAC Name

{[(4S,6S)-2,3,5-trihydroxy-4-({hydroxy[(2R)-3-(octadec-11-enoyloxy)-2-(octadeca-6,9,12-trienoyloxy)propoxy]phosphoryl}oxy)-6-(phosphonooxy)cyclohexyl]oxy}phosphonic acid

Traditional Name

[(4S,6S)-2,3,5-trihydroxy-4-{[hydroxy(2R)-3-(octadec-11-enoyloxy)-2-(octadeca-6,9,12-trienoyloxy)propoxyphosphoryl]oxy}-6-(phosphonooxy)cyclohexyl]oxyphosphonic acid

CAS Registry Number

None

SMILES

[H][C@@](COC(=O)CCCCCCCCCC=CCCCCCC)(COP(O)(=O)O[C@@]1([H])C(O)C(O)C(OP(O)(O)=O)[C@@]([H])(OP(O)(O)=O)C1O)OC(=O)CCCCC=CCC=CCC=CCCCCC

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/h12-15,18,20,24,26,37,40-45,48-50H,3-11,16-17,19,21-23,25,27-36H2,1-2H3,(H,57,58)(H2,51,52,53)(H2,54,55,56)/t37-,40?,41?,42?,43+,44?,45+/m1/s1

InChI Key

PQMAXMUERDBESE-LFTNFPGXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylinositol-4,5-bisphosphates. These are phosphatidylinositol bisphosphates in which the two phosphate groups are at C-4 and C-5 of the inositol moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoinositol phosphates

Direct Parent

Phosphatidylinositol-4,5-bisphosphates

Alternative Parents

Substituents

Diacylglycerophosphoinositol-4,5-bisphosphate
Diacylglycerophosphoinositol
Glycerophosphoinositol
Inositol phosphate
Dialkyl phosphate
Monoalkyl phosphate
Fatty acid ester
Cyclohexanol
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Dicarboxylic acid or derivatives
Cyclitol or derivatives
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

All Tissues (HMDB: HMDB0010078)

Organ

Brain (HMDB: HMDB0010078)

Cellular substructure

Membrane (HMDB: HMDB0010078)
Extracellular (HMDB: HMDB0010078)

Source

Exogenous

Exogenous (HMDB: HMDB0010078)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0010078)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.045 g/L	ALOGPS
logP	5.59	ALOGPS
logP	9.08	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	0.63	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	302.57 Å²	ChemAxon
Rotatable Bond Count	42	ChemAxon
Refractivity	255.18 m³·mol⁻¹	ChemAxon
Polarizability	108.4 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027261

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for PIP2(18:1(11Z)/18:3(6Z,9Z,12Z)) (CFc000006117)

MOL for CFc000006117 (PIP2(18:1(11Z)/18:3(6Z,9Z,12Z)))

3D MOL for CFc000006117 (PIP2(18:1(11Z)/18:3(6Z,9Z,12Z)))

3D SDF for CFc000006117 (PIP2(18:1(11Z)/18:3(6Z,9Z,12Z)))

3D-SDF for CFc000006117 (PIP2(18:1(11Z)/18:3(6Z,9Z,12Z)))

PDB for CFc000006117 (PIP2(18:1(11Z)/18:3(6Z,9Z,12Z)))

3D PDB for CFc000006117 (PIP2(18:1(11Z)/18:3(6Z,9Z,12Z)))

SMILES for CFc000006117 (PIP2(18:1(11Z)/18:3(6Z,9Z,12Z)))

INCHI for CFc000006117 (PIP2(18:1(11Z)/18:3(6Z,9Z,12Z)))

Structure for CFc000006117 (PIP2(18:1(11Z)/18:3(6Z,9Z,12Z)))

3D Structure for CFc000006117 (PIP2(18:1(11Z)/18:3(6Z,9Z,12Z)))