Milk Composition Database: Showing metabocard for PC(15:0/18:1(9Z)) (BMDB0007939)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:47:31 UTC

Update Date

2020-06-04 19:48:49 UTC

MCDB ID

BMDB0007939

Secondary Accession Numbers

BMDB07939

Metabolite Identification

Common Name

PC(15:0/18:1(9Z))

Description

PC(15:0/18:1(9Z)), also known as PC(15:0/18:1) or PC(33:1), 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(15:0/18:1(9Z)) is considered to be a glycerophosphocholine lipid molecule. PC(15:0/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(15:0/18:1(9Z)) exists in all eukaryotes, ranging from yeast to humans. PC(15:0/18:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(15:0/18:1(9Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(15:0/18:1(9Z)) through the action of the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(15:0/18:1(9Z)) can be biosynthesized from CDP-choline and DG(15:0/18:1(9Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(15:0/18:1(9Z)) and L-serine can be converted into choline and PS(15:0/18:1(9Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(15:0/18:1(9Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(15:0/18:1(9Z)) pathway and phosphatidylethanolamine biosynthesis pe(15:0/18:1(9Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Pentadecanoyl-2-(9Z-octadecenoyl)-glycero-3-phosphocholine	HMDB
1-Pentadecanoyl-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine	HMDB
1-Pentadecanoyl-2-oleoyl-GPC	HMDB
1-Pentadecanoyl-2-oleoyl-GPC (15:0/18:1)	HMDB
GPC(15:0/18:1)	HMDB
PC(15:0/18:1)	HMDB
PC(15:0/18:1n9)	HMDB
PC(15:0/18:1W9)	HMDB
PC(33:1)	HMDB
Phosphatidylcholine(15:0/18:1)	HMDB
Phosphatidylcholine(15:0/18:1n9)	HMDB
Phosphatidylcholine(15:0/18:1W9)	HMDB
Phosphatidylcholine(33:1)	HMDB
1-Pentadecanoyl-2-oleoyl-sn-glycero-3-phosphocholine	HMDB
Gpcho(15:0/18:1)	HMDB
Gpcho(15:0/18:1n9)	HMDB
Gpcho(15:0/18:1W9)	HMDB
Gpcho(33:1)	HMDB
Lecithin	HMDB
1-Pentadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine	HMDB
PC(15:0/18:1(9Z))	Lipid Annotator

Chemical Formula

C₄₁H₈₀NO₈P

Average Molecular Weight

746.0496

Monoisotopic Molecular Weight

745.562155053

IUPAC Name

trimethyl(2-{[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(pentadecanoyloxy)propyl phosphonato]oxy}ethyl)azanium

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC

InChI Identifier

InChI=1S/C41H80NO8P/c1-6-8-10-12-14-16-18-20-21-22-24-26-28-30-32-34-41(44)50-39(38-49-51(45,46)48-36-35-42(3,4)5)37-47-40(43)33-31-29-27-25-23-19-17-15-13-11-9-7-2/h20-21,39H,6-19,22-38H2,1-5H3/b21-20-/t39-/m1/s1

InChI Key

ZEWLMKXMNQOCOQ-KUNNKMQBSA-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 (LMGP01011415 )

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	5.43	ALOGPS
logP	8.2	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	221.58 m³·mol⁻¹	ChemAxon
Polarizability	91.96 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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0isr-0000695200-5f1038942664ed664a4e	2016-09-19	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000200-4a4aae1c56f0d82c90bd	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0190001000-c7f76117f70c236043ed	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0036-4190000000-121c7fcb82ea62260c47	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000900-dea40d097d7939446bdb	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0000001900-e5028f86ed3b639928db	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0i00-0100691100-51e54c79a2c72ac6d3c8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000000900-775208a25e34adb911ea	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0080042900-d5b94dd8133a2470de34	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-1090100000-d15deeea9bbead7a02c2	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000000900-f838901a8cc5953bfd9d	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0000000900-af19b0d392073b08857d	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000j-0500390200-290208a30d762c099262	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000000900-33c3132d5b9a740ac908	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000t-0600000900-348610127b1bcbb5a47d	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900231200-e905fc1763966f86c3c8	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000000900-44b34785552db236c3b3	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0030000900-f336d6a4ef0e13237d72	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001l-0090000400-b0a7cb6c0bb919583a5d	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-17	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	1.45 +/- 0.04 uM	PMID: 30994344	details
Detected and Quantified	2.2 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	4.1 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	0.92 +/- 0.01 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0007939

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB025131

KNApSAcK ID

Not Available

Chemspider ID

24766614

KEGG Compound ID

C00157

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52922312

PDB ID

Not Available

ChEBI ID

133623

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(15:0/18:1(9Z)) (BMDB0007939)

Structure for BMDB0007939 (PC(15:0/18:1(9Z)))