Milk Composition Database: Showing metabocard for PC(16:0/16:0) (BMDB0000564)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

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Record Information

Version

1.0

Creation Date

2016-09-30 22:32:52 UTC

Update Date

2020-06-04 20:04:17 UTC

MCDB ID

BMDB0000564

Secondary Accession Numbers

BMDB00564

Metabolite Identification

Common Name

PC(16:0/16:0)

Description

PC(16:0/16:0), also known as DPPC or 16:0-16:0-PC, 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. Thus, PC(16:0/16:0) is considered to be a glycerophosphocholine lipid molecule. PC(16:0/16:0) exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. PC(16:0/16:0) exists in all eukaryotes, ranging from yeast to humans. In cattle, PC(16:0/16:0) is involved in the metabolic pathway called phospholipid biosynthesis pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Bis(hexadecanoyl)-sn-glycero-3-phosphocholine	ChEBI
1,2-Dipalmitoyl-L-lecithin	ChEBI
1,2-Dipalmitoyl-sn-glycero-3-phosphatidylcholine	ChEBI
1,2-Dipalmitoyl-sn-glycero-3-phosphocholine	ChEBI
1,2-Dipalmitoylphosphatidylcholine	ChEBI
1-16:0-2-16:0-Phosphatidylcholine	ChEBI
16:0-16:0-PC	ChEBI
Colfosceril palmitate	ChEBI
Colfoscerili palmitas	ChEBI
Dipalmitoyl phosphatidylcholine	ChEBI
Dipalmitoyl-GPC	ChEBI
Dipalmitoylphosphatidylcholine	ChEBI
GPC(16:0/16:0)	ChEBI
GPCho 16:0/16:0	ChEBI
GPCho(16:0/16:0)	ChEBI
Palmitate de colfosceril	ChEBI
Palmitato de colfoscerilo	ChEBI
PC 16:0/16:0	ChEBI
PC(32:0)	ChEBI
Phosphatidylcholine 16:0/16:0	ChEBI
Phosphatidylcholine(16:0/16:0)	ChEBI
Phosphatidylcholine(32:0)	ChEBI
Colfosceril palmitic acid	Generator
Palmitic acid de colfosceril	Generator
1,2-Dipalmitoyl-rac-glycero-3-phosphocholine	HMDB
Lecithin	HMDB
1,2-Dihexadecanoyl-rac-glycero-3-phosphocholine	HMDB
GPCho(32:0)	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
1,2-Bis(palmitoyl)-sn-glycero-3-phosphocholine	HMDB
1,2-Dihexadecanoyl-sn-glycerol-3-phosphorylcholine	HMDB
1,2-Dipalmitoyl-3-sn-phosphatidylcholine	HMDB
1,2-Dipalmitoyl-L-3-phosphatidylcholine	HMDB
1,2-Dipalmitoyl-L-a-lecithin	HMDB
1,2-Dipalmitoyl-L-a-phosphatidylcholine	HMDB
1,2-Dipalmitoyl-L-alpha-lecithin	HMDB
1,2-Dipalmitoyl-L-alpha-phosphatidylcholine	HMDB
1,2-Dipalmitoyl-L-phosphatidylcholine	HMDB
1,2-Dipalmitoyl-sn-3-glycerophosphocholine	HMDB
1,2-Dipalmitoyl-sn-glycero-3-phosphorylcholine	HMDB
1,2-Dipalmitoyl-sn-glycerol-3-phosphocholine	HMDB
1,2-Dipalmitoyl-sn-glycerophosphocholine	HMDB
1,2-Dipalmitoyl-sn-glycerophosphorylcholine	HMDB
1,2-Dipalmitoyl-sn-glyceryl-3-phosphocholine	HMDB
1,2-Dipalmitoyl-sn-phosphatidylcholine	HMDB
1,2-Dipalmitoylglycero-3-phosphocholine	HMDB
1,2-L-a-Dipalmitoylphosphatidylcholine	HMDB
1,2-L-alpha-Dipalmitoylphosphatidylcholine	HMDB
b,g-Dipalmitoyl L-a-phosphatidylcholine	HMDB
b,g-Dipalmitoyl L-alpha-phosphatidylcholine	HMDB
b,g-Dipalmitoyl-L-(a)-lecithin	HMDB
b,g-Dipalmitoyl-L-phosphatidylcholine	HMDB
Dihexadecanoyl-sn-glycero-3-phosphocholine	HMDB
Dipalmitoyl L-a-phosphatidylcholine	HMDB
Dipalmitoyl L-alpha-phosphatidylcholine	HMDB
Dipalmitoyl-L-3-glycerylphosphorylcholine	HMDB
Dipalmitoyl-L-a-lecithin	HMDB
Dipalmitoyl-L-a-phosphatidylcholine	HMDB
Dipalmitoyl-L-alpha-lecithin	HMDB
Dipalmitoyl-L-alpha-phosphatidylcholine	HMDB
Dipalmitoyl-sn-3-phosphatidylcholine	HMDB
DPPC	HMDB
L-1,2-Dipalmitoyl-a-lecithin	HMDB
L-1,2-Dipalmitoyl-alpha-lecithin	HMDB
L-1,2-Dipalmitoylphosphatidylcholine	HMDB
L-a-1,2-Dipalmitoyl lecithin	HMDB
L-a-Dipalmitoylecithin	HMDB
L-a-Dipalmitoyllecithin	HMDB
L-a-Dipalmitoylphosphatidylcholine	HMDB
L-a-DPPC	HMDB
L-alpha-1,2-Dipalmitoyl lecithin	HMDB
L-alpha-Dipalmitoylecithin	HMDB
L-alpha-Dipalmitoyllecithin	HMDB
L-alpha-Dipalmitoylphosphatidylcholine	HMDB
L-alpha-DPPC	HMDB
L-b,g-Dipalmitoyl-a-lecithin	HMDB
L-b,g-Dipalmitoyl-a-phosphatidylcholine	HMDB
L-b,g-Dipalmitoyl-alpha-lecithin	HMDB
L-b,g-Dipalmitoyl-alpha-phosphatidylcholine	HMDB
L-b,g-Dipalmitoylphosphatidylcholine	HMDB
L-Dipalmitoyl lecithin	HMDB
L-DPPC	HMDB
PC Aa C32:0	HMDB
sn-3-Dipalmitoyllecithin	HMDB
1,2-Dipalmitoyl-GPC	HMDB
PC(16:0/16:0)	Lipid Annotator
1,2-Distearoyl-glycero-3-phosphocholine	HMDB

Chemical Formula

C₄₀H₈₀NO₈P

Average Molecular Weight

734.0389

Monoisotopic Molecular Weight

733.562155053

IUPAC Name

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

Traditional Name

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

CAS Registry Number

63-89-8

SMILES

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

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

Chemical Taxonomy

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 )

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
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	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum - IT 40V, negative	splash10-066r-0060100900-b6bff2ff205808890e0b	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 1V, positive	splash10-001i-0900000000-455598e8d7de92b66a2d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 1V, positive	splash10-0udi-0000290000-79bb58a12a550b728584	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - IT 30V, positive	splash10-001i-0900000400-ed1d6ef09691e9bb1b3e	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 51V, positive	splash10-001i-0000000900-012345aef55bfeb67201	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 51V, positive	splash10-004j-0000900000-208fe5d1fc5dcb9e1787	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 51V, positive	splash10-0002-0000029000-0cc983f3015a15000bcb	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 23V, positive	splash10-001r-0000000900-fa22d7b44b6ecf7bf3cb	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 33V, positive	splash10-001i-0500000900-6608b50815a9b5d35f04	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 51V, positive	splash10-001i-0900000000-9afadd11d3d3f123032d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 68V, positive	splash10-001i-2900000000-ce1e31a52e9cb1245e69	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 85V, positive	splash10-001r-4900000000-d399948e3d53f292acf4	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 124V, positive	splash10-0079-9800000000-58fcb9ea0920120df254	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 137V, positive	splash10-0079-9700000000-1bd1b9fb29d82e116b29	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 162V, positive	splash10-007a-9600000000-f4a52586e5510140e994	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 189V, positive	splash10-0072-9400000000-494bd7a2e515e6c62d17	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 223V, positive	splash10-0002-9100000000-548cf59f4be7b55dd942	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 258V, positive	splash10-0002-9000000000-852b94593bcfb0db899c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 309V, positive	splash10-0002-9000000000-1c426c57d21ff7447e74	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 51V, positive	splash10-002k-0000900200-dfdc7f3a135b07486248	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 51V, positive	splash10-014i-0000900000-875312e72ac68920d8df	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 51V, positive	splash10-01q9-0980000000-e120b0535f2910e5dbe8	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-e904df388d2d70397c9f	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000900-18b2f9e577dc5a9bfcb8	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900211200-e76cb9b9e105ad69b570	2017-10-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	10.4 +/- 0.4 uM	PMID: 30994344	details
Detected and Quantified	12.5 +/- 0.5 uM	PMID: 30994344	details
Detected and Quantified	15.1 +/- 0.3 uM	PMID: 30994344	details
Detected and Quantified	10.2 +/- 0.3 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0000564

DrugBank ID

DB09114

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022121

KNApSAcK ID

Not Available

Chemspider ID

398235

KEGG Compound ID

C00157

BioCyc ID

1-2-DIPALMITOYLPHOSPHATIDYLCHOLINE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5548

PubChem Compound

452110

PDB ID

Not Available

ChEBI ID

72999

References

Synthesis Reference

Bouirig, H.; Eloy, D.; Jardon, P. Formation and reactivity of the singlet oxygen photosensitized by hypericin in the liposomes of dipalmitoylphosphatidylcholine. Evidence of delayed oxidation. Journal de Chimie Physique et de Physico-Chimie Biologique (1992), 89(6), 1391-411.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Showing metabocard for PC(16:0/16:0) (BMDB0000564)

Structure for BMDB0000564 (PC(16:0/16:0))