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PC(14:0/20:4(5Z,8Z,11Z,14Z))

PubChem CID
24778634
Structure
PC(14:0/20:4(5Z,8Z,11Z,14Z))_small.png
Molecular Formula
Synonyms
  • PC(14:0/20:4(5Z,8Z,11Z,14Z))
  • PC(14:0/20:4)
  • Phosphatidylcholine(14:0/20:4)
  • GPCho(14:0/20:4)
  • GPCho(14:0/20:4n6)
Molecular Weight
754.0 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2008-05-14
  • Modify:
    2025-01-18
Description
1-tetradecanoyl-2-[(5Z,8Z,11Z,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine is a phosphatidylcholine 34:4 in which teh acyl groups specified at positions 1 and 2 are tetradecanoyl and (5Z,8Z,11Z,14Z)-eicosatetraenoyl respectively. It is a phosphatidylcholine 34:4 and a tetradecanoate ester. It is functionally related to an arachidonic acid.
PC(14:0/20:4(5Z,8Z,11Z,14Z)) is a metabolite found in or produced by Saccharomyces cerevisiae.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
PC(14:0/20:4(5Z,8Z,11Z,14Z)).png

1.2 3D Status

Conformer generation is disallowed since too many atoms, too flexible

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl]oxy-3-tetradecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

InChI=1S/C42H76NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-17-15-13-11-9-7-2/h14,16,19-20,22-23,27,29,40H,6-13,15,17-18,21,24-26,28,30-39H2,1-5H3/b16-14-,20-19-,23-22-,29-27-/t40-/m1/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

SRQSAJRUMDQMMS-NLDJLLEISA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.4 SMILES

CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C42H76NO8P
Computed by PubChem 2.1 (PubChem release 2019.06.18)

2.3 Other Identifiers

2.3.1 ChEBI ID

2.3.2 HMDB ID

2.3.3 Lipid Maps ID (LM_ID)

2.3.4 Metabolomics Workbench ID

2.3.5 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
754.0 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
11.5
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
8
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
38
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
753.53085538 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
753.53085538 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
111 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
52
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1030
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
4
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2019.01.04)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Collision Cross Section

285.0 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Sample Type: Human plasma; Dataset: Ambiguous Lipids]

289.6 Ų [M+CH3COO]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human bronchoalveolar lavage fluid (BALF); Dataset: Ambiguous Lipids]

281.2 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Sample Type: Human plasma; Dataset: Ambiguous Lipids]

3.3 Chemical Classes

3.3.1 Lipids

Lipids -> Ambiguous Lipids
Lipids -> Glycerophospholipids [GP] -> Glycerophosphocholines [GP01] -> Diacylglycerophosphocholines [GP0101]

5 Chemical Vendors

6 Drug and Medication Information

6.1 Biomarker Information

7 Pharmacology and Biochemistry

7.1 Human Metabolite Information

7.1.1 Tissue Locations

All Tissues

7.1.2 Cellular Locations

  • Extracellular
  • Membrane

7.1.3 Metabolite Pathways

7.2 Biochemical Reactions

8 Associated Disorders and Diseases

Disease
Pregnancy
References

PubMed: 2994907, 663967, 12698507, 17061063, 3252730, 12833386, 17704099, 16925883, 22420377, 18059417, 22494326, 23159745, 23313728, 23535240, 24704061

The Merck Manual, 17th ed. Mark H. Beers, MD, Robert Berkow, MD, eds. Whitehouse Station, NJ: Merck Research Labs, 1999.

Disease
Obesity
References

PubMed: 15899597, 17264178, 16253646, 2401584, 1783639, 26505825, 17408529, 18997681, 24740590, 23108202, 26910390

Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children

Disease
Eosinophilic esophagitis
References
Mordechai, Hien, and David S. Wishart

9 Literature

9.1 Consolidated References

9.2 Chemical Co-Occurrences in Literature

9.3 Chemical-Gene Co-Occurrences in Literature

9.4 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 Chemical Co-Occurrences in Patents

10.3 Chemical-Gene Co-Occurrences in Patents

11 Interactions and Pathways

11.1 Pathways

12 Taxonomy

13 Classification

13.1 ChEBI Ontology

13.2 LIPID MAPS Classification

13.3 CCS Classification - Baker Lab

13.4 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. Baker Lab, Chemistry Department, The University of North Carolina at Chapel Hill
    PC(14:0_20:4)
    CCS Classification - Baker Lab
    https://tarheels.live/bakerlab/
  2. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  3. ChEBI
    1-tetradecanoyl-2-[(5Z,8Z,11Z,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:86102
  4. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
    PC(14:0/20:4(5Z,8Z,11Z,14Z))
    https://www.ymdb.ca/compounds/YMDB01819
  5. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
    PC(14:0/20:4(5Z,8Z,11Z,14Z))
    http://www.hmdb.ca/metabolites/HMDB0007883
  6. MarkerDB
    LICENSE
    This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
    https://markerdb.ca/
    PC(14:0/20:4(5Z,8Z,11Z,14Z))
    https://markerdb.ca/chemicals/2177
  7. Metabolomics Workbench
  8. Natural Product Activity and Species Source (NPASS)
  9. Rhea - Annotated Reactions Database
    LICENSE
    Rhea has chosen to apply the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/). This means that you are free to copy, distribute, display and make commercial use of the database in all legislations, provided you credit (cite) Rhea.
    https://www.rhea-db.org/help/license-disclaimer
  10. Wikidata
    PC(14:0/20:4(5Z,8Z,11Z,14Z))
    https://www.wikidata.org/wiki/Q27158900
  11. PubChem
  12. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS