Bovine Metabolome Database: Showing metabocard for PC(18:1(9Z)/18:1(9Z)) (BMDB0000593)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:33:17 UTC

Update Date

2020-06-04 20:44:40 UTC

BMDB ID

BMDB0000593

Secondary Accession Numbers

BMDB00593

Metabolite Identification

Common Name

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

Description

PC(18:1(9Z)/18:1(9Z)) , also known as dielaidinoyl lecithin or 1,2-DOCPC, 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. PC(18:1(9Z)/18:1(9Z)) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R-(Z,Z))-(7-Oleoyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18-enyl)trimethylammonium 4-oxide	ChEBI
1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine	ChEBI
1,2-Dioleoyl-L-alpha-lecithin	ChEBI
1-(9Z)-Octadecenoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine	ChEBI
1-C18:1(Omega-9)-2-C18:1(omega-9)-phosphatidylcholine	ChEBI
Dioleoyl lecithin	ChEBI
Dioleoyl phosphatidylcholine	ChEBI
PC 18:1	ChEBI
PC(18:1(9Z)/18:1(9Z))	ChEBI
PC(18:1/18:1)	ChEBI
Phosphatidylcholine 18:1	ChEBI
1,2-Dioleoyl-L-a-lecithin	Generator
1,2-Dioleoyl-L-α-lecithin	Generator
1,2-Di-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine	HMDB
1,2-Dioleoyl-sn-glycerol-3-ethylphosphocholine	MeSH
Dioleylphosphatidylcholine	MeSH
1,2-Oleoylphosphatidylcholine, (L-alpha)-(R-(Z,Z))-isomer	MeSH
Dielaidoylphosphatidylcholine	MeSH
Dioleoylphosphatidylcholine	MeSH
1,2-Dioleoylglycerophosphocholine	MeSH
1,2-Oleoyl-sn-glycero-3-phosphocholine	MeSH
DOPC	MeSH
Dielaidinoyl lecithin	MeSH
1,2-DOCPC	MeSH
1,2-Dioleoyl glycerophosphocholine	MeSH
1,2-Dioleoyl-sn-glycero-3-phosphocholine	MeSH
1,2-Oleoylphosphatidylcholine	MeSH
1,2-Dioleoyl-GPC	HMDB
1,2-Dioleoyl-sn-glycero-phosphatidylcholine	HMDB
GPC(18:1(9Z)/18:1(9Z))	HMDB
GPC(18:1/18:1)	HMDB
GPC(18:1n9/18:1n9)	HMDB
GPC(18:1w9/18:1w9)	HMDB
GPC(36:2)	HMDB
GPCho(18:1(9Z)/18:1(9Z))	HMDB
GPCho(18:1/18:1)	HMDB
GPCho(18:1n9/18:1n9)	HMDB
GPCho(18:1w9/18:1w9)	HMDB
GPCho(36:2)	HMDB
PC(18:1n9/18:1n9)	HMDB
PC(18:1w9/18:1w9)	HMDB
PC(36:2)	HMDB
Phosphatidylcholine(18:1(9Z)/18:1(9Z))	HMDB
Phosphatidylcholine(18:1/18:1)	HMDB
Phosphatidylcholine(18:1n9/18:1n9)	HMDB
Phosphatidylcholine(18:1w9/18:1w9)	HMDB
Phosphatidylcholine(36:2)	HMDB
1,2-Dioleoyl-3-sn-phosphatidylcholine	HMDB
1,2-Dioleoyl-sn-glycero-3-phosphochline	HMDB
1,2-Dioleoyl-sn-glycero-3-phosphorylcholine	HMDB
1,2-Dioleoyl-sn-phosphatidylcholine	HMDB
1,2-Dioleoylphosphatidylcholine	HMDB
1,2-Dioleyl-L-lecithin	HMDB
Dioleoyl L-alpha-lecithin	HMDB
Dioleoyl L-α-lecithin	HMDB
Dioleoyl-3-sn-phosphatidylcholine	HMDB
Dioleoyl-L-alpha-glycerophosphocholine	HMDB
Dioleoyl-L-alpha-glycerophosphorylcholine	HMDB
Dioleoyl-L-alpha-phosphatidylcholine	HMDB
Dioleoyl-L-α-glycerophosphocholine	HMDB
Dioleoyl-L-α-glycerophosphorylcholine	HMDB
Dioleoyl-L-α-phosphatidylcholine	HMDB
Dioleoyllecithin	HMDB
L-Dioleoyl lecithin	HMDB
L-Dioleoylphosphatidylcholine	HMDB
L-alpha-Di(cis-9-octadecanoyl) lecithin	HMDB
L-alpha-Dioleoyl phosphatidylcholine	HMDB
L-alpha-Dioleoyllecithin	HMDB
L-alpha-Dioleylphosphatidylcholine	HMDB
L-α-Di(cis-9-octadecanoyl) lecithin	HMDB
L-α-Dioleoyl phosphatidylcholine	HMDB
L-α-Dioleoyllecithin	HMDB
L-α-Dioleylphosphatidylcholine	HMDB
sn-3-Dioleoyllecithin	HMDB
1,2-Dioleoylglycerol-3-phosphorylcholine	HMDB
1,2-Dioleoylglyceryl-3-phosphorylcholine	HMDB
1,2-Dioleoyllecithin	HMDB
Dioleoylglycerophosphocholine	HMDB
Dioleoylglycerophosphorylcholine	HMDB
Dioleoylglycerylphosphorylcholine	HMDB
Dioleyl lecithin	HMDB
Dioleyl phosphatidylcholine	HMDB

Chemical Formula

C₄₄H₈₄NO₈P

Average Molecular Weight

786.1134

Monoisotopic Molecular Weight

785.593455181

IUPAC Name

(2-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

68737-67-7

SMILES

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

InChI Identifier

InChI=1S/C44H84NO8P/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/h20-23,42H,6-19,24-41H2,1-5H3/b22-20-,23-21-/t42-/m1/s1

InChI Key

SNKAWJBJQDLSFF-NVKMUCNASA-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 36:2 (CHEBI:74669 )
Diacylglycerophosphocholines (LMGP01010890 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Intracellular membrane
Membrane

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	5.78	ALOGPS
logP	9.17	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	42	ChemAxon
Refractivity	236.5 m³·mol⁻¹	ChemAxon
Polarizability	96.97 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000000900-36f689a3cf8b031c9ce5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0019-0600000900-4df68b8e85813f4b5ad8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-1900021300-f15a88b3adc3a38193cb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000090-53a8e01f33b2af13f226	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0000000190-64f46bdfe255d6a5b5e4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004k-0900139110-7365097ffb2d5d55b434	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000900-64c382f846ba04194d31	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000000900-6c06686879d9f7790e62	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-0200249400-1ae2411ef15a63cb3b2d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000000900-e54f4b7d729e27672b37	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0019-0600000900-3a2440aaca7e87ec13a5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-1900021300-24d60344b49a468b0469	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000000900-23df8d3c4971511f3b91	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0050030900-b121f3ff4b078b5df33e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-1090200000-673c166236d767f9289e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000000090-683d2aaf9f12a9d08614	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0010000090-37042360a3899f1fdc23	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00f0-0090000090-06eeedb644af6eeff7ec	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

Milk
Ruminal Fluid

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Milk	Detected and Quantified	5.82 +/- 0.04 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	7.0 +/- 0.2 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	9.5 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	5.48 +/- 0.03 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Ruminal Fluid	Detected and Quantified	0.263 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.104 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.019 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.642 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.564 +/- 0.381 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.501 +/- 0.341 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.531 +/- 0.436 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.601 +/- 0.735 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0062690

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8525772

KEGG Compound ID

Not Available

BioCyc ID

CPD-2181

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10350317

PDB ID

Not Available

ChEBI ID

74669

References

Synthesis Reference

Tokuyama, Satoru; Morisawa, Kazuya; Nakachi, Osamu; Nakano, Yoshiro; Miki, Tomoharu. Preparation of phosphatidylcholines. Jpn. Kokai Tokkyo Koho (1989), 6 pp.

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.

Enzymes

Enzyme Details

1. Phosphatidylethanolamine N-methyltransferase

General function:: Involved in phosphatidylethanolamine N-methyltransferas
Specific function:: Catalyzes the three sequential steps of the methylation pathway of phosphatidylcholine biosynthesis, the SAM-dependent methylation of phosphatidylethanolamine (PE) to phosphatidylmonomethylethanolamine (PMME), PMME to phosphatidyldimethylethanolamine (PDME), and PDME to phosphatidylcholine (PC).
Gene Name:: PEMT
Uniprot ID:: Q7YRH6
Molecular weight:: 22018.0

Reactions

S-Adenosylmethionine + PE-NMe2(18:1(9Z)/18:1(9Z)) → S-Adenosylhomocysteine + PC(18:1(9Z)/18:1(9Z))	details

Enzyme Details

2. Phosphatidylserine synthase 1

General function:: Not Available
Specific function:: Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. In membranes, PTDSS1 catalyzes mainly the conversion of phosphatidylcholine. Also converts, in vitro and to a lesser extent, phosphatidylethanolamine (By similarity).
Gene Name:: PTDSS1
Uniprot ID:: Q2KHY9
Molecular weight:: 55416.0

Reactions

PC(18:1(9Z)/18:1(9Z)) + L-Serine → Choline + PS(18:1(9Z)/18:1(9Z))	details

Showing metabocard for PC(18:1(9Z)/18:1(9Z)) (BMDB0000593)

Structure for BMDB0000593 (PC(18:1(9Z)/18:1(9Z)))

Enzymes

Reactions

Reactions