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PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))

PubChem CID
53478611
Structure
PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))_small.png
Molecular Formula
Synonyms
  • PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))
  • PC(36:5)
  • 1-tetradecanoyl-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycero-3-phosphocholine
  • CHEBI:89583
  • GPCho(14:0/22:5n6)
Molecular Weight
780.1 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2011-11-09
  • Modify:
    2025-01-04
Description
PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z)) is a 1,2-diacyl-sn-glycero-3-phosphocholine.
PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z)) has been reported in Lysiphlebia japonica and Aphis gossypii with data available.
PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z)) is a metabolite found in or produced by Saccharomyces cerevisiae.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z)).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-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyl]oxy-3-tetradecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

InChI=1S/C44H78NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-24-25-27-29-31-33-35-37-44(47)53-42(41-52-54(48,49)51-39-38-45(3,4)5)40-50-43(46)36-34-32-30-28-26-17-15-13-11-9-7-2/h14,16,19-20,22-23,25,27,31,33,42H,6-13,15,17-18,21,24,26,28-30,32,34-41H2,1-5H3/b16-14-,20-19-,23-22-,27-25-,33-31-/t42-/m1/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

MGUTYWPZCZBAGE-JZDIRDTQSA-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)CC/C=C\C/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

C44H78NO8P
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
780.1 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
12.1
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
39
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
779.54650544 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
779.54650544 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
54
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1100
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
5
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

284.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with phosphatidylcholines (ESI+) and phosphatidylethanolamines (ESI-)]
284.5 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

286.6 Ų [M+H]+ [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

286.7 Ų [M+H]+ [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

275 Ų [M-CH3]- [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

289.3 Ų [M+H]+ [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

297.3 Ų [M+HCOO]- [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

285.7 Ų [M+H]+ [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

291.3 Ų [M+H]+ [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

297.9 Ų [M+HCOO]- [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

291.5 Ų [M+HCOO]- [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

297.8 Ų [M+CH3COO]- [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

288 Ų [M+H]+ [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

296.7 Ų [M+HCOO]- [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

292.1 Ų [M+HCOO]- [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

286.9 Ų [M+H]+ [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

284.9 Ų [M+H]+ [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

289.9 Ų [M+H]+ [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

285.6 Ų [M+H]+ [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

289.4 Ų [M+H]+ [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

275.6 Ų [M-CH3]- [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

284.8 Ų [M+H]+ [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

290 Ų [M+H]+ [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

292.7 Ų [M+HCOO]- [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

290.9 Ų [M+HCOO]- [CCS Type: TIMS; Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

3.3 Chemical Classes

3.3.1 Lipids

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

5 Drug and Medication Information

5.1 Biomarker Information

6 Pharmacology and Biochemistry

6.1 Human Metabolite Information

6.1.1 Tissue Locations

All Tissues

6.1.2 Cellular Locations

  • Extracellular
  • Membrane

6.1.3 Metabolite Pathways

6.2 Biochemical Reactions

7 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

8 Literature

8.1 Consolidated References

9 Interactions and Pathways

9.1 Pathways

10 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

11 Classification

11.1 ChEBI Ontology

11.2 LIPID MAPS Classification

11.3 CCSBase Classification

11.4 LOTUS Tree

11.5 MolGenie Organic Chemistry Ontology

12 Information Sources

  1. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  2. ChEBI
  3. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
    PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))
    https://www.wikidata.org/wiki/Q27161780
  4. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
    PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))
    https://www.ymdb.ca/compounds/YMDB01824
  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(14:0/22:5(4Z,7Z,10Z,13Z,16Z))
    http://www.hmdb.ca/metabolites/HMDB0007890
  6. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  7. Natural Product Activity and Species Source (NPASS)
  8. MarkerDB
    LICENSE
    This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
    https://markerdb.ca/
    PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))
    https://markerdb.ca/chemicals/2184
  9. Metabolomics Workbench
  10. Wikidata
    PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))
    https://www.wikidata.org/wiki/Q27161780
  11. PubChem
  12. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS