Milk Composition Database: Showing metabocard for PC(16:1(9Z)/20:0) (BMDB0008010)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:48:56 UTC

Update Date

2020-06-04 19:57:47 UTC

MCDB ID

BMDB0008010

Secondary Accession Numbers

BMDB08010

Metabolite Identification

Common Name

PC(16:1(9Z)/20:0)

Description

PC(16:1(9Z)/20:0), also known as dimyristoyl lecithin or GPC(28:0), 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(16:1(9Z)/20:0) is considered to be a glycerophosphocholine lipid molecule. PC(16:1(9Z)/20:0) is a drug. PC(16:1(9Z)/20:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:1(9Z)/20:0) exists in all eukaryotes, ranging from yeast to humans. PC(16:1(9Z)/20:0) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:1(9Z)/20:0) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:1(9Z)/20:0) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:1(9Z)/20:0) can be biosynthesized from CDP-choline and DG(16:1(9Z)/20:0/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:1(9Z)/20:0) and L-serine can be converted into choline and PS(16:1(9Z)/20:0) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(16:1(9Z)/20:0) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:1(9Z)/20:0) pathway and phosphatidylethanolamine biosynthesis pe(16:1(9Z)/20:0) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Phosphatidylcholine(16:1/20:0)	HMDB
PC(36:1)	HMDB
1-Palmitoleoyl-2-arachidonyl-sn-glycero-3-phosphocholine	HMDB
Lecithin	HMDB
PC(16:1/20:0)	HMDB
Phosphatidylcholine(36:1)	HMDB
GPCho(16:1/20:0)	HMDB
1-(9Z-Hexadecenoyl)-2-eicosanoyl-sn-glycero-3-phosphocholine	HMDB
GPCho(36:1)	HMDB
PC(16:1(9Z)/20:0)	Lipid Annotator

Chemical Formula

C₄₄H₈₆NO₈P

Average Molecular Weight

788.1293

Monoisotopic Molecular Weight

787.609105245

IUPAC Name

(2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-(icosanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-(icosanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

18194-24-6

SMILES

[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C44H86NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-25-27-29-31-33-35-37-44(47)53-42(41-52-54(48,49)51-39-38-45(3,4)5)40-50-43(46)36-34-32-30-28-26-24-19-17-15-13-11-9-7-2/h17,19,42H,6-16,18,20-41H2,1-5H3/b19-17-/t42-/m1/s1

InChI Key

YFGYYMPGHQJKLU-HTDYWKJCSA-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 (LMGP01011488 )

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	5.89	ALOGPS
logP	9.53	ChemAxon
logS	-7.6	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	43	ChemAxon
Refractivity	235.39 m³·mol⁻¹	ChemAxon
Polarizability	98.21 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	splash10-001i-0000772900-28890ec97227dfa185e9	2016-09-19	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f79-0092000300-571301de81e0acc4eb8d	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udr-0090000100-a383ae0caf39262fe489	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-1173-4092000000-3e3699d545c1b538b70e	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000090-5649a580e0942e999145	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000000190-fad619901ff8ea0e25d7	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002b-0900449110-87bf2a9cf397d1a26d34	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000900-973b6e2c5af7633f95b6	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000000900-7a868a8ad9eb6f9e7bbd	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03ec-0200669400-fdc3e666e49c30e03434	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000000900-575f764ae3b8a734c007	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0019-0600000900-1e34e2e526af2e3adeda	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900221300-1f6989dcf29117ae7723	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000000900-11c57723ac725e930e50	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0063010900-0e7e32b74107abcc9218	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-114u-4195100000-984d30a64567bab15739	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000000090-c7d2a706ee4c08cac004	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0011000090-2742a3c4a801520550fb	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0y4i-0099000090-7eb206876c1608911f2a	2021-09-25	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

Concentrations

Status	Value	Reference	Details
Detected and Quantified	5.46 +/- 0.02 uM	PMID: 30994344	details
Detected and Quantified	6.5 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	8.6 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	5.23 +/- 0.03 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0008010

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB025058

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

52922458

PDB ID

Not Available

ChEBI ID

89736

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(16:1(9Z)/20:0) (BMDB0008010)

Structure for BMDB0008010 (PC(16:1(9Z)/20:0))