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L-Palmitoylcarnitine

PubChem CID
11953816
Structure
L-Palmitoylcarnitine_small.png
Molecular Formula
Synonyms
  • L-Palmitoylcarnitine
  • Palmitoyl-L-carnitine
  • 2364-67-2
  • O-palmitoyl-L-carnitine
  • Hexadecanoyl-L-carnitine
Molecular Weight
399.6 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2006-11-22
  • Modify:
    2025-01-18
Description
O-palmitoyl-L-carnitine is an O-acyl-L-carnitine in which the acyl group is specified as palmitoyl (hexadecanoyl). It has a role as an EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor, a human metabolite and a mouse metabolite. It is an O-palmitoylcarnitine, a saturated fatty acyl-L-carnitine and a long-chain fatty acyl-L-carnitine. It is functionally related to a hexadecanoic acid.
L-Palmitoylcarnitine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
L-Palmitoylcarnitine has been reported in Homo sapiens and Apis cerana with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
L-Palmitoylcarnitine.png

1.2 3D Status

Conformer generation is disallowed since too flexible

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3R)-3-hexadecanoyloxy-4-(trimethylazaniumyl)butanoate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C23H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h21H,5-20H2,1-4H3/t21-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

XOMRRQXKHMYMOC-OAQYLSRUSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCCCCCCCCCCCCCCC(=O)O[C@H](CC(=O)[O-])C[N+](C)(C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C23H45NO4
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 UNII

2.3.3 ChEBI ID

2.3.4 ChEMBL ID

2.3.5 DSSTox Substance ID

2.3.6 KEGG ID

2.3.7 Lipid Maps ID (LM_ID)

2.3.8 Metabolomics Workbench ID

2.3.9 Pharos Ligand ID

2.3.10 Wikidata

2.3.11 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Hexadecanoylcarnitine
  • Palmitoylcarnitine
  • Palmitylcarnitine

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
399.6 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
7.7
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
19
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
399.33485892 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
399.33485892 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
66.4 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
28
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
398
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
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
0
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 2021.10.14)

3.2 Experimental Properties

3.2.1 Collision Cross Section

215.68 Ų [M]+ [CCS Type: TIMS; Method: single field calibrated]

214 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

204.49 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

3.3 Chemical Classes

3.3.1 Cosmetics

Cosmetic ingredients (Palmitoyl Carnitine) -> CIR (Cosmetic Ingredient Review)
Skin conditioning
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

3.3.2 Lipids

Fatty Acyls [FA] -> Fatty esters [FA07] -> Fatty acyl carnitines [FA0707]

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 MS-MS

1 of 2
NIST Number
1152365
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
400.3421
Total Peaks
14
m/z Top Peak
341.3
m/z 2nd Highest
239.2
m/z 3rd Highest
257.2
Thumbnail
Thumbnail
2 of 2
NIST Number
1006051
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
400.3421
Total Peaks
2
m/z Top Peak
341
m/z 2nd Highest
239
m/z 3rd Highest
0
Thumbnail
Thumbnail

4.1.2 LC-MS

1 of 7
View All
Authors
da Silva KM, Iturrospe E, van de Lavoir M, Robeyns R, University of Antwerp, Belgium
Instrument
Agilent 6530 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10 eV
Fragmentation Mode
CID
Retention Time
0.218 min
Precursor m/z
400.3421
Precursor Adduct
[M+H]+
Top 5 Peaks

400.3427 999

85.0288 675

60.0817 85

341.268 77

239.2359 24

Thumbnail
Thumbnail
License
CC BY
2 of 7
View All
Authors
BGC, Helmholtz Zentrum Muenchen
Instrument
maXis plus UHR-ToF-MS, Bruker Daltonics
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10
Fragmentation Mode
CID
Column Name
BEH C18 1.7um, 2.1x100mm, Waters
Retention Time
5.781 min
Precursor m/z
400.3421
Precursor Adduct
[M+H]+
Top 5 Peaks

400.3423 999

402.349 32

85.0277 6

341.268 2

Thumbnail
Thumbnail
License
CC BY

4.1.3 Other MS

1 of 3
View All
MS Category
Experimental
MS Type
Other
Precursor Type
M+H
Precursor m/z
400.342
Instrument
Orbitrap
Ionization Mode
positive
Retention Time
CCS:
Top 5 Peaks

401.345398 100

341.26889 89.19

239.236969 22.07

342.2724 7.42

257.247559 2.76

Thumbnail
Thumbnail
2 of 3
View All
MS Category
Experimental
MS Type
Other
Precursor Type
2M+H
Precursor m/z
799.677
Instrument
Orbitrap
Ionization Mode
positive
Retention Time
CCS:
Top 5 Peaks

400.341309 100

401.344635 27.97

801.681946 3.28

341.268341 2.32

400.445862 1.59

Thumbnail
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6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Associated Foods

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Vitamin B Complex
A group of water-soluble vitamins, some of which are COENZYMES. (See all compounds classified as Vitamin B Complex.)

8.2 Biochemical Reactions

9 Use and Manufacturing

9.1 Uses

Cosmetic Ingredient Review Link
CIR ingredient: Palmitoyl Carnitine
EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125

9.1.1 Use Classification

Cosmetics -> Skin conditioning
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

10 Toxicity

10.1 Toxicological Information

10.1.1 Acute Effects

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Nature Journal References

11.5 Chemical Co-Occurrences in Literature

11.6 Chemical-Gene Co-Occurrences in Literature

11.7 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Pathways

14 Biological Test Results

14.1 BioAssay Results

15 Taxonomy

WormJam Metabolites Local CSV for MetFrag | DOI:10.5281/zenodo.3403364
WormJam: A consensus C. elegans Metabolic Reconstruction and Metabolomics Community and Workshop Series, Worm, 6:2, e1373939, DOI:10.1080/21624054.2017.1373939
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

16 Classification

16.1 MeSH Tree

16.2 ChEBI Ontology

16.3 LIPID MAPS Classification

16.4 KEGG: Lipid

16.5 ChemIDplus

16.6 ChEMBL Target Tree

16.7 EPA CPDat Classification

16.8 NORMAN Suspect List Exchange Classification

16.9 CCSBase Classification

16.10 EPA DSSTox Classification

16.11 LOTUS Tree

16.12 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  5. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  6. ChEBI
  7. E. coli Metabolome Database (ECMDB)
    LICENSE
    ECMDB is offered to the public as a freely available resource.
    https://ecmdb.ca/citations
  8. 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/
  9. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
  10. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  11. Cosmetic Ingredient Review (CIR)
  12. EPA Chemical and Products Database (CPDat)
  13. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  14. ECI Group, LCSB, University of Luxembourg
    LICENSE
    Data: CC-BY 4.0; Code: Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    O-palmitoyl-L-carnitine
  15. KNApSAcK Species-Metabolite Database
  16. Natural Product Activity and Species Source (NPASS)
    (3R)-3-Hexadecanoyloxy-4-(Trimethylazaniumyl)Butanoate
    https://bidd.group/NPASS/compound.php?compoundID=NPC326651
  17. FooDB
    LICENSE
    FooDB 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 (FooDB) and the original publication.
    https://foodb.ca/about
  18. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  19. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  20. MassBank Europe
  21. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  22. Metabolomics Workbench
  23. Nature Chemical Biology
  24. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  25. Pharos
    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
  26. 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
  27. Springer Nature
  28. Wikidata
  29. Wikipedia
  30. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  31. PubChem
  32. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  33. PATENTSCOPE (WIPO)
CONTENTS