Milk Composition Database: Showing metabocard for PC(18:0/18:1(9Z)) (BMDB0008038)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:49:30 UTC

Update Date

2020-06-04 19:57:48 UTC

MCDB ID

BMDB0008038

Secondary Accession Numbers

BMDB08038

Metabolite Identification

Common Name

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

Description

PC(18:0/18:1(9Z)), also known as sopc or GPC(18:0/18:1), 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(18:0/18:1(9Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:0/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:0/18:1(9Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:0/18:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:0/18:1(9Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:0/18:1(9Z)); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. In addition, Cytidine monophosphate and PC(18:0/18:1(9Z)) can be biosynthesized from CDP-choline and DG(18:0/18:1(9Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. In cattle, PC(18:0/18:1(9Z)) is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(18:0/18:1(9Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R)-3-(Octadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl 2-(trimethylammonio)ethyl phosphate	ChEBI
1-18:0-2-18:1-Phosphatidylcholine	ChEBI
1-Octadecanoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine	ChEBI
1-Octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine	ChEBI
1-Stearoyl-2-oleoyl-GPC	ChEBI
1-Stearoyl-2-oleoyl-GPC (18:0/18:1)	ChEBI
1-Steroyl-2-oleoylphosphatidylcholine	ChEBI
18:0-18:1-PC	ChEBI
GPC(18:0/18:1)	ChEBI
GPCho 18:0/18:1(9Z)	ChEBI
L-alpha-1-Stearoyl-2-oleoyl lecithin	ChEBI
PC 18:0/18:1(9Z)	ChEBI
PC(18:0/18:1n9)	ChEBI
PC(18:0/18:1omega9)	ChEBI
PC(18:0/18:1W9)	ChEBI
Phosphatidylcholine(18:0/18:1(9Z))	ChEBI
Phosphatidylcholine(18:0/18:1)	ChEBI
Phosphatidylcholine(18:0/18:1n9)	ChEBI
Phosphatidylcholine(18:0/18:1omega9)	ChEBI
Phosphatidylcholine(18:0/18:1W9)	ChEBI
Phosphatidylcholine(36:1)	ChEBI
SOPC	ChEBI
(2R)-3-(Octadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl 2-(trimethylammonio)ethyl phosphoric acid	Generator
L-a-1-Stearoyl-2-oleoyl lecithin	Generator
L-Α-1-stearoyl-2-oleoyl lecithin	Generator
GPCho(36:1)	Lipid Annotator, HMDB
PC(36:1)	Lipid Annotator, HMDB
1-stearoyl-2-oleoyl-sn-glycero-3-phosphocholine	Lipid Annotator, MeSH, HMDB
PC(18:0/18:1)	Lipid Annotator, HMDB
Lecithin	Lipid Annotator, HMDB
PC(18:0/18:1(9Z))	Lipid Annotator
GPCho(18:0/18:1)	Lipid Annotator, HMDB
1-Stearoyl-2-oleoyl-sn-glycero-3-phosphocholine, (e)-isomer	MeSH, HMDB
1-Stearoyl-2-oleoyl-sn-glycero-3-phosphocholine, (S-(Z))-isomer	MeSH, HMDB
1-Stearoyl-2-oleoyl lecithin	MeSH, HMDB
1-Stearoyl-2-oleoyl-sn-glycero-3-phosphocholine, (R-(Z))-isomer	MeSH, HMDB
1-SOPC	MeSH, HMDB
1-Stearoyl-2-oleoyl-sn-3-glycerophosphocholine	MeSH, HMDB
1-Stearoyl-2-oleoyl glycerylphosphorylcholine	HMDB
1-Stearoyl-2-oleoyl-sn-glycero-phosphatidylcholine	HMDB
1-Stearoyl-2-oleoyllecithin	HMDB
1-Stearoyl-2-oleoylphosphatidylcholine	HMDB
1-Stearyl-2-oleoyl-3-sn-glycerophosphatidylcholine	HMDB
GPC(18:0/18:1(9Z))	HMDB
GPC(18:0/18:1n9)	HMDB
GPC(18:0/18:1w9)	HMDB
GPC(36:1)	HMDB
GPCho(18:0/18:1(9Z))	HMDB
GPCho(18:0/18:1n9)	HMDB
GPCho(18:0/18:1w9)	HMDB
L-alpha-1-Stearoyl-2-oleoylphosphatidylcholine	HMDB
L-α-1-Stearoyl-2-oleoylphosphatidylcholine	HMDB

Chemical Formula

C₄₄H₈₆NO₈P

Average Molecular Weight

788.1293

Monoisotopic Molecular Weight

787.609105245

IUPAC Name

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

Traditional Name

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

CAS Registry Number

6753-56-6

SMILES

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

InChI Identifier

InChI=1S/C44H86NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h21,23,42H,6-20,22,24-41H2,1-5H3/b23-21-/t42-/m1/s1

InChI Key

ATHVAWFAEPLPPQ-VRDBWYNSSA-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

1-octadecanoyl-2-octadecenoyl-sn-glycero-3-phosphocholine (CHEBI:75034 )
Diacylglycerophosphocholines (LMGP01010761 )

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	97.79 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	splash10-000i-0000000900-b859f2c3b3c1a8178429	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0019-0600000900-740e271e86363b8b605a	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900041300-22e6346bd3881ccf6ad0	2017-10-04	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	splash10-004j-0900369110-8d8283d716b8945882e5	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000000090-c7d2a706ee4c08cac004	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0030000090-9becebc4c350016d45de	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0089-0090000040-58b0dfd010ce87ff0a8f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000000900-11c57723ac725e930e50	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0019-0071010900-5a423108e9ed5868292a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-2092200000-f53135f214f9fe93df45	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000000900-575f764ae3b8a734c007	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0019-0600000900-1e34e2e526af2e3adeda	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0089-1900041300-20b479e3bfdf095f4186	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000900-973b6e2c5af7633f95b6	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000000900-7a868a8ad9eb6f9e7bbd	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-0200498400-d8a93635e28c18a04dd4	2021-09-24	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

HMDB0008038

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24766704

KEGG Compound ID

Not Available

BioCyc ID

CPD-8278

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24778825

PDB ID

Not Available

ChEBI ID

75034

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(18:0/18:1(9Z)) (BMDB0008038)

Structure for BMDB0008038 (PC(18:0/18:1(9Z)))