ChemFOnt: Showing chemical card for PIP(20:3(8Z,11Z,14Z)/22:6(5Z,8E,10Z,13Z,15E,19Z)-2OH(7S, 17S)) (CFc000259452)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 02:51:10 UTC

Chemfont ID

CFc000259452

Molecule Identification

Common Name

PIP(20:3(8Z,11Z,14Z)/22:6(5Z,8E,10Z,13Z,15E,19Z)-2OH(7S, 17S))

Definition

PIP(20:3(8Z,11Z,14Z)/22:6(5Z,8E,10Z,13Z,15E,19Z)-2OH(7S, 17S)) is an oxidized phosphatidylinositol phosphate (PIP). As other PIPs, oxidized phosphatidylinositol phosphates are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to a phosphorylated inositol (hexahydroxycyclohexane). Phosphatidylinositol phosphates 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. Phosphatidylinositol phosphates can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. PIP(20:3(8Z,11Z,14Z)/22:6(5Z,8E,10Z,13Z,15E,19Z)-2OH(7S, 17S)), in particular, consists of one chain of 8Z,11Z,14Z-eicosatrienoyl at the C-1 position and one chain of Resolvin D5 at the C-2 position. The most important phosphatidylinositol phosphate in both quantitative and biological terms is phosphatidylinositol 4-phosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes. Phosphatidylinositol 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

Value	Source
{[(1R,3S)-3-({[(2R)-2-{[(7R,8E,10Z,13Z,17S,19Z)-7,17-dihydroxydocosa-5,8,10,13,15,19-hexaenoyl]oxy}-3-[(8Z,11Z)-icosa-8,11,14-trienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2,4,5,6-tetrahydroxycyclohexyl]oxy}phosphonate	HMDB

Chemical Formula

C₅₁H₈₂O₁₈P₂

Average Molecular Weight

1045.147

Monoisotopic Molecular Weight

1044.497639796

IUPAC Name

{[(1R,3S)-3-({[(2R)-2-{[(5Z,7R,8E,10Z,13Z,15E,17S,19Z)-7,17-dihydroxydocosa-5,8,10,13,15,19-hexaenoyl]oxy}-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2,4,5,6-tetrahydroxycyclohexyl]oxy}phosphonic acid

Traditional Name

[(1R,3S)-3-{[(2R)-2-{[(5Z,7R,8E,10Z,13Z,15E,17S,19Z)-7,17-dihydroxydocosa-5,8,10,13,15,19-hexaenoyl]oxy}-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2,4,5,6-tetrahydroxycyclohexyl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](OP(O)(O)=O)C1O)OC(=O)CCC\C=C/[C@@H](O)\C=C\C=C/C\C=C/C=C/[C@@H](O)C\C=C/CC

InChI Identifier

InChI=1S/C51H82O18P2/c1-3-5-7-8-9-10-11-12-13-14-15-16-17-18-22-25-31-37-44(54)65-39-43(40-66-71(63,64)69-51-48(58)46(56)47(57)50(49(51)59)68-70(60,61)62)67-45(55)38-32-26-30-36-42(53)35-29-24-21-19-20-23-28-34-41(52)33-27-6-4-2/h6,9-10,12-13,15-16,20-21,23-24,27-30,34-36,41-43,46-53,56-59H,3-5,7-8,11,14,17-19,22,25-26,31-33,37-40H2,1-2H3,(H,63,64)(H2,60,61,62)/b10-9-,13-12-,16-15-,23-20-,24-21-,27-6-,34-28+,35-29+,36-30-/t41-,42-,43+,46?,47?,48?,49?,50+,51-/m0/s1

InChI Key

DGTBUADFWFCYLC-ABJOIZDCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycerophosphoinositol phosphates. These are lipids containing a common glycerophosphate skeleton linked to at least one fatty acyl chain and an inositol-5-phosphate moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoinositol phosphates

Direct Parent

Glycerophosphoinositol phosphates

Alternative Parents

Substituents

Glycerophosphoinositol phosphate
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

All cells and tissues (HMDB: HMDB0279936)

Cellular substructure

Organelle

Endoplasmic reticulum (PMID: 20519312)

Golgi apparatus membrane (PMID: 20519312)
Cell membrane (PMID: 20519312)

Source

Endogenous

Endogenous (HMDB: HMDB0279936)

Process

Naturally occurring process

Biological process

Cellular process

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0056 g/L	ALOGPS
logP	5.78	ALOGPS
logP	7.75	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	1.08	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	296.5 Å²	ChemAxon
Rotatable Bond Count	41	ChemAxon
Refractivity	280.38 m³·mol⁻¹	ChemAxon
Polarizability	112.69 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

HMDB0279936

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

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

156983288

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for PIP(20:3(8Z,11Z,14Z)/22:6(5Z,8E,10Z,13Z,15E,19Z)-2OH(7S, 17S)) (CFc000259452)

MOL for CFc000259452 (PIP(20:3(8Z,11Z,14Z)/22:6(5Z,8E,10Z,13Z,15E,19Z)-2OH(7S, 17S)))

3D MOL for CFc000259452 (PIP(20:3(8Z,11Z,14Z)/22:6(5Z,8E,10Z,13Z,15E,19Z)-2OH(7S, 17S)))

3D SDF for CFc000259452 (PIP(20:3(8Z,11Z,14Z)/22:6(5Z,8E,10Z,13Z,15E,19Z)-2OH(7S, 17S)))

3D-SDF for CFc000259452 (PIP(20:3(8Z,11Z,14Z)/22:6(5Z,8E,10Z,13Z,15E,19Z)-2OH(7S, 17S)))

PDB for CFc000259452 (PIP(20:3(8Z,11Z,14Z)/22:6(5Z,8E,10Z,13Z,15E,19Z)-2OH(7S, 17S)))

3D PDB for CFc000259452 (PIP(20:3(8Z,11Z,14Z)/22:6(5Z,8E,10Z,13Z,15E,19Z)-2OH(7S, 17S)))

SMILES for CFc000259452 (PIP(20:3(8Z,11Z,14Z)/22:6(5Z,8E,10Z,13Z,15E,19Z)-2OH(7S, 17S)))

INCHI for CFc000259452 (PIP(20:3(8Z,11Z,14Z)/22:6(5Z,8E,10Z,13Z,15E,19Z)-2OH(7S, 17S)))

Structure for CFc000259452 (PIP(20:3(8Z,11Z,14Z)/22:6(5Z,8E,10Z,13Z,15E,19Z)-2OH(7S, 17S)))

3D Structure for CFc000259452 (PIP(20:3(8Z,11Z,14Z)/22:6(5Z,8E,10Z,13Z,15E,19Z)-2OH(7S, 17S)))