Milk Composition Database: Showing metabocard for PC(18:0/18:0) (BMDB0008036)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:49:28 UTC

Update Date

2020-06-04 20:02:11 UTC

MCDB ID

BMDB0008036

Secondary Accession Numbers

BMDB08036

Metabolite Identification

Common Name

PC(18:0/18:0)

Description

PC(18:0/18:0), also known as gpcho(36:0) or PC (18:0)2, 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(18:0/18:0) is considered to be a glycerophosphocholine lipid molecule. PC(18:0/18:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:0/18:0) exists in all eukaryotes, ranging from yeast to humans. PC(18:0/18:0) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:0/18:0) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:0/18:0); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:0/18:0) can be biosynthesized from CDP-choline and DG(18:0/18:0/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:0/18:0) and L-serine can be converted into choline and PS(18:0/18:0); which is catalyzed by the enzyme phosphatidylserine synthase. In cattle, PC(18:0/18:0) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:0/18:0) pathway and phosphatidylethanolamine biosynthesis pe(18:0/18:0) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Dioctadecanoyl-sn-glycero-3-phosphocholine	ChEBI
1,2-Distearoyl-sn-3-phosphacholine	ChEBI
Distearoyl phosphatidylcholine	ChEBI
GPC(18:0/18:0)	ChEBI
GPCho(18:0/18:0)	ChEBI
GPCho(36:0)	ChEBI
PC (18:0)2	ChEBI
PC 18:0/18:0	ChEBI
PC(36:0)	ChEBI
Phosphatidylcholine(18:0/18:0)	ChEBI
Phosphatidylcholine(36:0)	ChEBI
1,2-Distearoyl-sn-glycero-3-phosphocholine	HMDB
1,2-Distearoyllecithin, (S)-isomer	HMDB
1,2-Distearoyllecithin, (+-)-isomer	HMDB
Distearoylglycerophosphocholine	HMDB
1,2-Distearoyllecithin	HMDB
Distearoylphosphatidylcholine	HMDB
1,2-Distearoyllecithin, (R)-isomer	HMDB
1,2-Distearoylphosphatidylcholine	HMDB
1,2-Distearoyl-rac-glycero-3-phosphocholine	HMDB
Lecithin	HMDB
1,2-Dioctadecanoyl-rac-glycero-3-phosphocholine	HMDB
PC(18:0/18:0)	Lipid Annotator
4-Hydroxy-N,N,N-trimethyl-10-oxo-7-((1-oxooctadecyl)oxy)-3,5,9-trioxa-4-phosphahepta cosan-1-aminium hydroxide, inner salt, 4-oxide	MeSH

Chemical Formula

C₄₄H₈₈NO₈P

Average Molecular Weight

790.1452

Monoisotopic Molecular Weight

789.624755309

IUPAC Name

(2-{[(2R)-2,3-bis(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2,3-bis(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

816-94-4

SMILES

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

InChI Identifier

InChI=1S/C44H88NO8P/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/h42H,6-41H2,1-5H3/t42-/m1/s1

InChI Key

NRJAVPSFFCBXDT-HUESYALOSA-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 36:0 (CHEBI:83718 )
Diacylglycerophosphocholines (LMGP01010006 )

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	5.92	ALOGPS
logP	9.89	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	44	ChemAxon
Refractivity	234.27 m³·mol⁻¹	ChemAxon
Polarizability	99.02 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
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 31V, negative	splash10-0089-0000000590-0aad18afe34a7c3e4d4c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 39V, negative	splash10-00e9-0000000950-0e01653ba450f4cf2474	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 45V, negative	splash10-00e9-0030000910-5f5f6ea7c69c11446a37	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 52V, negative	splash10-0089-0090000600-450dc346ec045426f41a	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 58V, negative	splash10-001i-0090000200-ac0ebb03ecad4a755352	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 64V, negative	splash10-001i-0090000000-0cda3c7a3fd1efdab660	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 78V, negative	splash10-001i-0090000000-8039839adbbb06bce8cc	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 97V, negative	splash10-001i-0090000000-32180842465e1f0ca062	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 118V, negative	splash10-001i-0090000000-add4cfd543c3c7500150	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 143V, negative	splash10-001i-1090000000-731977fa0efe340b2c9b	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 170V, negative	splash10-003r-6090000000-10e012ff7fe106b8a5f0	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 210V, negative	splash10-004i-9000000000-003f91760dbf6d21ebe7	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 55V, negative	splash10-00di-0000000900-ed2638f28be0dc446783	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 22V, positive	splash10-0006-0000000900-08c46febfbe4ee762593	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 34V, positive	splash10-000x-0600000900-f13e1162895079b39581	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 48V, positive	splash10-001i-0900000000-095cbcd6f3947470459d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 74V, positive	splash10-001i-0900000000-b0b68022ed94da51246c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 99V, positive	splash10-001i-2900000000-552209425d26c02a0476	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 124V, positive	splash10-008i-6900000000-b39bf3dd8da792e30123	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 161V, positive	splash10-0079-9600000000-6622c8393c18efd1dd28	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 198V, positive	splash10-007a-9400000000-a1be01e41d76c34ddef8	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 236V, positive	splash10-0072-9200000000-df8e8bf2dc44c5e36e28	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000900-ddeff1f077816b130f0b	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000x-0600000900-cbf5b5700da15bd27faf	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900021300-9f90c5ee485e939b0d38	2017-10-04	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	0.66 +/- 0.01 uM		PMID: 30994344	details
Detected and Quantified	0.74 +/- 0.01 uM		PMID: 30994344	details

External Links

HMDB ID

HMDB0008036

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB025227

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

94190

PDB ID

Not Available

ChEBI ID

83718

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(18:0/18:0) (BMDB0008036)

Structure for BMDB0008036 (PC(18:0/18:0))