Showing Compound PIP(18:0/16:0) (FDB027133)

Record Information

Version

1.0

Creation date

2011-09-21 01:20:13 UTC

Update date

2015-07-21 06:59:00 UTC

Primary ID

FDB027133

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

PIP(18:0/16:0)

Description

PIP(18:0/16:0) is a phosphatidylinositol phosphate. 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. Phosphatidylinositols phosphates 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. PIP(18:0/16:0), in particular, consists of one chain of stearic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. 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. Phosphatidylinositols phosphates are usually present at low levels only in tissues, typically at about 1 to 3% of the concentration of phosphatidylinositol. [HMDB]

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
1-Octadecanoyl-2-hexadecanoyl-sn-glycero-3-O-(1'-myo-inositol-3'-ate)	HMDB
1-octadecanoyl-2-hexadecanoyl-sn-glycero-3-phospho-(1'-myo-inositol-3'-phosphate)	Lipid Annotator, HMDB
1-octadecanoyl-2-hexadecanoyl-sn-glycero-3-phosphoinositol-phosphate	Lipid Annotator, HMDB
1-Phosphatidyl-1D-myo-inositol-4-phosphate	HMDB
1-Stearoyl-2-palmitoyl-sn-glycero-3-oinositol-ate	HMDB
1-stearoyl-2-palmitoyl-sn-glycero-3-phosphoinositol-phosphate	Lipid Annotator, HMDB
Atidylinositol ate(18:0/16:0)	HMDB
Phosphatidylinositol Phosphate(18:0/16:0)	Lipid Annotator, HMDB
Phosphatidylinositol Phosphate(34:0)	Lipid Annotator, HMDB
PIP(18:0/16:0)	Lipid Annotator

Showing 1 to 10 of 13 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.0073 g/L	ALOGPS
logP	6.03	ALOGPS
logP	9.76	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	1.08	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	256.04 Å²	ChemAxon
Rotatable Bond Count	42	ChemAxon
Refractivity	230.64 m³·mol⁻¹	ChemAxon
Polarizability	103.82 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

Chemical Formula

C43H84O16P2

IUPAC name

{[(1R,3S)-3-({[(2R)-2-(hexadecanoyloxy)-3-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2,4,5,6-tetrahydroxycyclohexyl]oxy}phosphonic acid

InChI Identifier

InChI=1S/C43H84O16P2/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-36(44)55-33-35(57-37(45)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2)34-56-61(53,54)59-43-40(48)38(46)39(47)42(41(43)49)58-60(50,51)52/h35,38-43,46-49H,3-34H2,1-2H3,(H,53,54)(H2,50,51,52)/t35-,38?,39?,40?,41?,42-,43+/m1/s1

InChI Key

FKUKFDBBDBZQON-CILQWCOCSA-N

Isomeric SMILES

[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](OP(O)(O)=O)C1O)OC(=O)CCCCCCCCCCCCCCC

Average Molecular Weight

919.065

Monoisotopic Molecular Weight

918.523459664

Classification

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

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect:

Touch:

Smooth

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Blood

Tissue and substructures:

All tissues

Organ and components:

Brain

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Biochemical process:

Cellular process:

Cell signaling

Role

Industrial application:

Food and nutrition:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00or-5011054129-aeab5fe989051ec6c817	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4j-9011050341-128deb6fbd187bb7d61f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-3069200000-e5f129c5b019a7427c98	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0004001009-cebd6c14fe685ffbbf3c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02ei-5096005001-0950efb052f65487d243	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9034100110-145b5d6a2b9251319860	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

24767827

ChEMBL ID

Not Available

KEGG Compound ID

C00626

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB09946

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Lecithin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Anatidae	Expected but not quantified	Not Available	HMDB
Beefalo	Expected but not quantified	Not Available	HMDB
Bison	Expected but not quantified	Not Available	HMDB
Buffalo	Expected but not quantified	Not Available	HMDB
Cattle (Beef, Veal)	Expected but not quantified	Not Available	HMDB
Chicken	Expected but not quantified	Not Available	HMDB
Columbidae (Dove, Pigeon)	Expected but not quantified	Not Available	HMDB
Deer	Expected but not quantified	Not Available	HMDB
Domestic goat	Expected but not quantified	Not Available	HMDB
Domestic pig	Expected but not quantified	Not Available	HMDB

Showing 1 to 10 of 29 entries

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
GPI ethanolamine phosphate transferase 1	PIGN	O95427
GPI ethanolamine phosphate transferase 2	PIGG	Q5H8A4
GPI ethanolamine phosphate transferase 3	PIGO	Q8TEQ8
GPI mannosyltransferase 1	PIGM	Q9H3S5
GPI mannosyltransferase 2	PIGV	Q9NUD9
GPI mannosyltransferase 3	PIGB	Q92521
GPI mannosyltransferase 4	PIGZ	Q86VD9
GPI transamidase component PIG-S	PIGS	Q96S52
GPI transamidase component PIG-T	PIGT	Q969N2
N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase	PIGL	Q9Y2B2