Milk Composition Database: Showing metabocard for PC(22:1(13Z)/14:1(9Z)) (BMDB0008559)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-10-03 17:24:12 UTC

Update Date

2020-06-04 20:44:45 UTC

MCDB ID

BMDB0008559

Secondary Accession Numbers

BMDB08559

Metabolite Identification

Common Name

PC(22:1(13Z)/14:1(9Z))

Description

PC(22:1(13Z)/14:1(9Z)), also known as lecithin or PC(36:2), 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(22:1(13Z)/14:1(9Z)) is considered to be a glycerophosphocholine lipid molecule. PC(22:1(13Z)/14:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(22:1(13Z)/14:1(9Z)) exists in all eukaryotes, ranging from yeast to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Lecithin	HMDB
PC(36:2)	HMDB
Phosphatidylcholine(36:2)	HMDB
1-Erucoyl-2-myristoleoyl-sn-glycero-3-phosphocholine	HMDB
Phosphatidylcholine(22:1/14:1)	HMDB
PC(22:1/14:1)	HMDB
GPCho(22:1/14:1)	HMDB
1-(13Z-Docosenoyl)-2-(9Z-tetradecenoyl)-sn-glycero-3-phosphocholine	HMDB
GPCho(36:2)	HMDB
PC(22:1(13Z)/14:1(9Z))	Lipid Annotator

Chemical Formula

C₄₄H₈₄NO₈P

Average Molecular Weight

786.1134

Monoisotopic Molecular Weight

785.593455181

IUPAC Name

(2-{[(2R)-3-[(13Z)-docos-13-enoyloxy]-2-[(9Z)-tetradec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-24-25-27-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-26-17-15-13-11-9-7-2/h13,15,19-20,42H,6-12,14,16-18,21-41H2,1-5H3/b15-13-,20-19-/t42-/m1/s1

InChI Key

CYQUGAJGPGKDFF-MHJIJCEHSA-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 (LMGP01012219 )

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	96.83 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-9154132400-7fc48bd46d0a6976f5eb	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0kni-6597112200-ce0c8933a91ca9ffa84d	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0080-9146022100-b96e262659994941d310	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00nr-0049000300-df5b2553129b31e59d6d	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-0029001000-eff189f74b3f73e4cdc7	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0573-7297100000-9c21e4cc9ff1b30def35	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000000900-23df8d3c4971511f3b91	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001r-0041020900-5a6938701ed9f4d9352b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-1139000000-fbeb5f5e4dcdf9a28a41	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000000090-683d2aaf9f12a9d08614	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0011000090-06338fba3431f5598089	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ii-0099000090-f6ade794dc5f49ce5904	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000000900-e54f4b7d729e27672b37	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0019-0600000900-3a2440aaca7e87ec13a5	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900221300-a38751f4c325dd7c0ac8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000090-53a8e01f33b2af13f226	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0000000190-64f46bdfe255d6a5b5e4	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002b-0700329110-97efa49e8e50e1a32606	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000900-64c382f846ba04194d31	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000000900-6c06686879d9f7790e62	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-0202469400-08602756fdb5bb814ce1	2021-09-23	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	5.82 +/- 0.04 uM	PMID: 30994344	details
Detected and Quantified	7.0 +/- 0.2 uM	PMID: 30994344	details
Detected and Quantified	9.5 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	5.48 +/- 0.03 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0008559

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB025749

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

53479167

PDB ID

Not Available

ChEBI ID

88741

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(22:1(13Z)/14:1(9Z)) (BMDB0008559)

Structure for BMDB0008559 (PC(22:1(13Z)/14:1(9Z)))