Showing Compound PC(16:0/16:0) (FDB022121)

Record Information

Version

1.0

Creation date

2011-09-21 00:08:47 UTC

Update date

2020-02-24 19:11:11 UTC

Primary ID

FDB022121

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

PC(16:0/16:0)

Description

PC(16:0/16:0) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines 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 16, 18 and 20 carbons are the most common. PC(16:0/16:0), in particular, consists of two chains of palmitic acid at the C-1 and C-2 positions. The palmitic acid moieties are derived from fish oils, milk fats, vegetable oils and animal fats. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Dipalmitoylphosphatidylcholine (DPPC) is the major constituent of pulmonary surfactant. It is also used for research purposes in studying liposomes, lipid bilayers, and model biological membranes. 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. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. [HMDB]

CAS Number

63-89-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(R)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-apentacosan-1-aminium 4-oxide hydroxide inner salt	HMDB
(R)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-apentacosan-1-aminium 4-oxide inner salt	HMDB
(R)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacosan-1-aminium 4-oxide hydroxide inner salt	HMDB
(R)-4-hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-Trioxa-4-phosphapentacosan-1-aminium 4-oxide hydroxide inner salt	hmdb
(R)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacosan-1-aminium 4-oxide inner salt	HMDB
(R)-4-hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-Trioxa-4-phosphapentacosan-1-aminium 4-oxide inner salt	hmdb
1,2-Bis(hexadecanoyl)-sn-glycero-3-ocholine	ChEBI
1,2-Bis(hexadecanoyl)-sn-glycero-3-phosphocholine	ChEBI
1,2-Bis(palmitoyl)-sn-glycero-3-ocholine	HMDB
1,2-Bis(palmitoyl)-sn-glycero-3-phosphocholine	HMDB

Showing 1 to 10 of 138 entries

Predicted Properties

Property	Value	Source
Water Solubility	2.4e-05 g/L	ALOGPS
logP	5.29	ALOGPS
logP	8.11	ChemAxon
logS	-7.5	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	111.19 Å²	ChemAxon
Rotatable Bond Count	40	ChemAxon
Refractivity	215.87 m³·mol⁻¹	ChemAxon
Polarizability	92 Å³	ChemAxon
Number of Rings	0	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

C40H80NO8P

IUPAC name

(2-{[(2R)-2,3-bis(hexadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

InChI Identifier

InChI=1S/C40H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3/t38-/m1/s1

InChI Key

KILNVBDSWZSGLL-KXQOOQHDSA-N

Isomeric SMILES

[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC

Average Molecular Weight

734.0389

Monoisotopic Molecular Weight

733.562155053

Classification

Description

Belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

Phosphatidylcholines

Alternative Parents

Substituents

Diacylglycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Amine
Organic salt
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

phosphatidylcholine 32:0 (CHEBI:72999 )
Diacylglycerophosphocholines (LMGP01010564 )

Ontology

Physiological effect

Organoleptic effect:

Touch:

Smooth

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Biochemical process:

Cellular process:

Cell signaling

Role

Biological role:

Industrial application:

Food and nutrition:

Pharmaceutical industry:

Pharmaceutical

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
MS/MS	LC-MS/MS Spectrum - IT 40V, negative	splash10-066r-0060100900-b6bff2ff205808890e0b	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 1V, positive	splash10-001i-0900000000-455598e8d7de92b66a2d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 1V, positive	splash10-0udi-0000290000-79bb58a12a550b728584	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - IT 30V, positive	splash10-001i-0900000400-ed1d6ef09691e9bb1b3e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 51V, positive	splash10-001i-0000000900-012345aef55bfeb67201	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 51V, positive	splash10-004j-0000900000-208fe5d1fc5dcb9e1787	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 51V, positive	splash10-0002-0000029000-0cc983f3015a15000bcb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 23V, positive	splash10-001r-0000000900-fa22d7b44b6ecf7bf3cb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 33V, positive	splash10-001i-0500000900-6608b50815a9b5d35f04	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 51V, positive	splash10-001i-0900000000-9afadd11d3d3f123032d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 68V, positive	splash10-001i-2900000000-ce1e31a52e9cb1245e69	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 85V, positive	splash10-001r-4900000000-d399948e3d53f292acf4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 124V, positive	splash10-0079-9800000000-58fcb9ea0920120df254	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 137V, positive	splash10-0079-9700000000-1bd1b9fb29d82e116b29	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 162V, positive	splash10-007a-9600000000-f4a52586e5510140e994	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 189V, positive	splash10-0072-9400000000-494bd7a2e515e6c62d17	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 223V, positive	splash10-0002-9100000000-548cf59f4be7b55dd942	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 258V, positive	splash10-0002-9000000000-852b94593bcfb0db899c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 309V, positive	splash10-0002-9000000000-1c426c57d21ff7447e74	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 51V, positive	splash10-002k-0000900200-dfdc7f3a135b07486248	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 51V, positive	splash10-014i-0000900000-875312e72ac68920d8df	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 51V, positive	splash10-01q9-0980000000-e120b0535f2910e5dbe8	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-e904df388d2d70397c9f	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000900-18b2f9e577dc5a9bfcb8	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900211200-e76cb9b9e105ad69b570	2017-10-04	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00564

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

PCF

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Dipalmitoylphosphatidylcholine

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

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
2-acylglycerol O-acyltransferase 2	MOGAT2	Q3SYC2
Acyl-protein thioesterase 1	LYPLA1	O75608
Acyl-protein thioesterase 2	LYPLA2	O95372
Choline kinase alpha	CHKA	P35790
Choline-phosphate cytidylyltransferase A	PCYT1A	P49585
Choline-phosphate cytidylyltransferase B	PCYT1B	Q9Y5K3
Eosinophil lysophospholipase	CLC	Q05315
Lecithin retinol acyltransferase	LRAT	O95237
Lysophosphatidylcholine acyltransferase 2	LPCAT2	Q7L5N7
Lysophospholipid acyltransferase 5	LPCAT3	Q6P1A2