Milk Composition Database: Showing metabocard for PC(18:3(6Z,9Z,12Z)/16:0) (BMDB0008166)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-10-03 17:15:10 UTC

Update Date

2020-06-04 20:41:44 UTC

MCDB ID

BMDB0008166

Secondary Accession Numbers

BMDB08166

Metabolite Identification

Common Name

PC(18:3(6Z,9Z,12Z)/16:0)

Description

PC(18:3(6Z,9Z,12Z)/16:0), also known as gpcho(18:3/16:0) or lecithin, 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(18:3(6Z,9Z,12Z)/16:0) is considered to be a glycerophosphocholine lipid molecule. PC(18:3(6Z,9Z,12Z)/16:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:3(6Z,9Z,12Z)/16:0) exists in all eukaryotes, ranging from yeast to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-g-Linolenoyl-2-palmitoyl-sn-glycero-3-phosphocholine	HMDB
GPCho(18:3/16:0)	HMDB
Lecithin	HMDB
Phosphatidylcholine(34:3)	HMDB
GPCho(34:3)	HMDB
Phosphatidylcholine(18:3/16:0)	HMDB
PC(18:3/16:0)	HMDB
1-(6Z,9Z,12Z-Octadecatrienoyl)-2-hexadecanoyl-sn-glycero-3-phosphocholine	HMDB
PC(34:3)	HMDB
PC(18:3(6Z,9Z,12Z)/16:0)	Lipid Annotator

Chemical Formula

C₄₂H₇₈NO₈P

Average Molecular Weight

756.0444

Monoisotopic Molecular Weight

755.546504989

IUPAC Name

(2-{[(2R)-2-(hexadecanoyloxy)-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C42H78NO8P/c1-6-8-10-12-14-16-18-20-21-23-24-26-28-30-32-34-41(44)48-38-40(39-50-52(46,47)49-37-36-43(3,4)5)51-42(45)35-33-31-29-27-25-22-19-17-15-13-11-9-7-2/h14,16,20-21,24,26,40H,6-13,15,17-19,22-23,25,27-39H2,1-5H3/b16-14-,21-20-,26-24-/t40-/m1/s1

InChI Key

MXPOYZQNXGPEDV-REAAISNBSA-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

Diacylglycerophosphocholines (LMGP01011646 )

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	5.46	ALOGPS
logP	7.92	ChemAxon
logS	-7.4	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	39	ChemAxon
Refractivity	228.42 m³·mol⁻¹	ChemAxon
Polarizability	90.71 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000900-deb054ff1e14f68ef680	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-0600000900-0998358a1aca7036ae80	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900231200-395dbf80736d8da3f685	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0pdi-0090000200-845f58b53b892522a702	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-0090001000-c76865ae1a67fd3fa83e	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-3090000000-a593c6908f6447a1760a	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000900-b5946ddd213bca84cd6e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000000900-8697b097e89237a32dd7	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0100390200-8c94611232ab673975aa	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000900-7d3df73fbaa9dffe7d9e	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-0600000900-785a8f601a463a4cb653	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900231200-1de475ad6e9d4945dbaf	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000000900-178043a88be6f491ac6f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0000000900-13496904f0fd4fc1981e	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0500190100-969d191b5a0b12f47eef	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000000900-7438791c506b384c79b0	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0030000900-871f854ac2854ad8d30b	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a96-0090000400-006075ca20ec6574d3e4	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000000900-3cb602c3acfc6a68ce4b	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-0091043700-1a363818e11280a106bc	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-4190300000-f1f90a927e3f9679a86d	2021-09-24	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	0.84 +/- 0.01 uM	PMID: 30994344	details
Detected and Quantified	0.98 +/- 0.04 uM	PMID: 30994344	details
Detected and Quantified	1.3 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	0.74 +/- 0.01 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0008166

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB025356

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

52922771

PDB ID

Not Available

ChEBI ID

89545

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

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(18:3(6Z,9Z,12Z)/16:0) (BMDB0008166)

Structure for BMDB0008166 (PC(18:3(6Z,9Z,12Z)/16:0))