Milk Composition Database: Showing metabocard for PC(18:1(9Z)/18:2(9Z,12Z)) (BMDB0008105)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:50:58 UTC

Update Date

2020-06-04 20:43:58 UTC

MCDB ID

BMDB0008105

Secondary Accession Numbers

BMDB08105

Metabolite Identification

Common Name

PC(18:1(9Z)/18:2(9Z,12Z))

Description

PC(18:1(9Z)/18:2(9Z,12Z)), also known as PC(18:1/18:2) or PC(18:1omega9/18:2omega6), 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(18:1(9Z)/18:2(9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:1(9Z)/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:1(9Z)/18:2(9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:1(9Z)/18:2(9Z,12Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:1(9Z)/18:2(9Z,12Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:1(9Z)/18:2(9Z,12Z)); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:1(9Z)/18:2(9Z,12Z)) can be biosynthesized from CDP-choline and DG(18:1(9Z)/18:2(9Z,12Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:1(9Z)/18:2(9Z,12Z)) and L-serine can be converted into choline and PS(18:1(9Z)/18:2(9Z,12Z)) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(18:1(9Z)/18:2(9Z,12Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:1(9Z)/18:2(9Z,12Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:1(9Z)/18:2(9Z,12Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(9Z)-Octadecaenoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine	ChEBI
1-(9Z-Octadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine	ChEBI
1-C18:1(Omega-9)-2-C18:2(omega-6)-phosphatidylcholine	ChEBI
1-Oleoyl-2-linoleoyl-GPC	ChEBI
1-Oleoyl-2-linoleoyl-GPC (18:1/18:2)	ChEBI
GPC(18:1/18:2)	ChEBI
PC(18:1/18:2)	ChEBI
PC(18:1Omega9/18:2omega6)	ChEBI
PC(36:3)	ChEBI
Phosphatidylcholine(18:1/18:2)	ChEBI
Phosphatidylcholine(18:1omega9/18:2omega6)	ChEBI
Phosphatidylcholine(36:3)	ChEBI
1-Oleoyl-2-linoleoyl-sn-glycero-3-phosphocholine	HMDB
GPCho(36:3)	HMDB
GPCho(18:1/18:2)	HMDB
Lecithin	HMDB
1-Oleoyl-2-linoleoyl lecithin	HMDB
1-Oleoyl-2-linoleoyl phosphatidylcholine	HMDB
1-Oleoyl-2-linoleoyl-sn-glycero-phosphatidylcholine	HMDB
GPC(18:1(9Z)/18:2(9Z,12Z))	HMDB
GPC(18:1n9/18:2n6)	HMDB
GPC(18:1W9/18:2W6)	HMDB
GPC(36:3)	HMDB
GPCho(18:1(9Z)/18:2(9Z,12Z))	HMDB
GPCho(18:1n9/18:2n6)	HMDB
GPCho(18:1W9/18:2W6)	HMDB
L-(+)-alpha-(Alpha'-oleoyl-beta-linoleoyl)glycerylphosphorylcholine	HMDB
L-(+)-Α-(α'-oleoyl-β-linoleoyl)glycerylphosphorylcholine	HMDB
L-(+)-Α-(α’-oleoyl-β-linoleoyl)glycerylphosphorylcholine	HMDB
PC(18:1n9/18:2n6)	HMDB
PC(18:1W9/18:2W6)	HMDB
Phosphatidylcholine(18:1(9Z)/18:2(9Z,12Z))	HMDB
Phosphatidylcholine(18:1n9/18:2n6)	HMDB
Phosphatidylcholine(18:1W9/18:2W6)	HMDB
PC(18:1(9Z)/18:2(9Z,12Z))	Lipid Annotator, ChEBI

Chemical Formula

C₄₄H₈₂NO₈P

Average Molecular Weight

784.0975

Monoisotopic Molecular Weight

783.577805117

IUPAC Name

trimethyl(2-{[(2R)-3-[(9Z)-octadec-9-enoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)azanium

Traditional Name

trimethyl(2-{[(2R)-3-[(9Z)-octadec-9-enoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)azanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C44H82NO8P/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/h15,17,20-23,42H,6-14,16,18-19,24-41H2,1-5H3/b17-15-,22-20-,23-21-/t42-/m1/s1

InChI Key

GDWULUGDXGHJIJ-VJHNMZKJSA-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 36:3 (CHEBI:74670 )
Diacylglycerophosphocholines (LMGP01010895 )

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	5.74	ALOGPS
logP	8.81	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	41	ChemAxon
Refractivity	237.62 m³·mol⁻¹	ChemAxon
Polarizability	93.97 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, Negative	splash10-001i-0090000400-673c4b41bf0baa3179b5	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01q9-0090001000-a565c7b509c80f248611	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01si-3090100000-d9f0aaac3713bc0352be	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000000900-f313232611c4c0c71d38	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0090020800-2f1b9f57c7195f8960ef	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-2190100000-5ec20bd547c21812e0b2	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000000090-02472e506be910245a7b	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0030000090-3c7d05d682b05a083951	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ai-0090000040-4c2666c7619b17b07955	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fs9-9051052400-a89d585222552400de65	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01c9-5393033100-37ce295c82fbf076874f	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0079-9056031100-7f29f68a8e68350100ba	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-016fbc06bd6c36a12e4f	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000900-7ba4362bb833d26b28b0	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ff0-1900041300-a8960ec50ee7c8790e73	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000900-f44acebd42271f9d37fe	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000000900-d39b20e156e47b15fe77	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0200498400-c711e23d2ffb1410e86b	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000090-1db30625399fdea6b457	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0000000190-671ed31d83ec847480a0	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dk-0900369110-e9eb218755dd4edd13b3	2021-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	3.24 +/- 0.04 uM	PMID: 30994344	details
Detected and Quantified	4.0 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	5.3 +/- 0.1 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0008105

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB030211

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

24778939

PDB ID

Not Available

ChEBI ID

74670

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(18:1(9Z)/18:2(9Z,12Z)) (BMDB0008105)

Structure for BMDB0008105 (PC(18:1(9Z)/18:2(9Z,12Z)))