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1,2-Dipalmitoylphosphatidylcholine

PubChem CID
6138
Structure
1,2-Dipalmitoylphosphatidylcholine_small.png
Molecular Formula
Synonyms
  • 2644-64-6
  • 1,2-DIPALMITOYLPHOSPHATIDYLCHOLINE
  • 1,2-Dipalmitoyl-rac-glycero-3-phosphocholine
  • 1,2-DIHEXADECANOYL-RAC-GLYCERO-3-PHOSPHOCHOLINE
  • 2797-68-4
Molecular Weight
734.0 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-01-04
Description
Synthetic phospholipid used in liposomes and lipid bilayers to study biological membranes. It is also a major constituent of PULMONARY SURFACTANTS.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
1,2-Dipalmitoylphosphatidylcholine.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

2,3-di(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C40H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

KILNVBDSWZSGLL-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C40H80NO8P
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2797-68-4

2.3.2 Deprecated CAS

107041-15-6, 159022-81-8, 173839-68-4, 215369-06-5, 2797-68-4, 36441-53-9, 67118-46-1, 82623-33-4, 90289-55-7

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 DSSTox Substance ID

2.3.6 HMDB ID

2.3.7 RXCUI

2.3.8 Wikidata

2.3.9 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 1,2 Dihexadecyl sn Glycerophosphocholine
  • 1,2 Dipalmitoyl Glycerophosphocholine
  • 1,2 Dipalmitoylphosphatidylcholine
  • 1,2-Dihexadecyl-sn-Glycerophosphocholine
  • 1,2-Dipalmitoyl-Glycerophosphocholine
  • 1,2-Dipalmitoylphosphatidylcholine
  • Dipalmitoyl Phosphatidylcholine
  • Dipalmitoylglycerophosphocholine
  • Dipalmitoyllecithin
  • Dipalmitoylphosphatidylcholine
  • Phosphatidylcholine, Dipalmitoyl

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
734.0 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
13.5
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
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
40
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
733.56215551 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
733.56215551 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
111 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
50
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
826
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
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
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 Physical Description

White powder; [Aldrich MSDS]

3.3 Chemical Classes

Biological Agents -> Plant Oils and Extracts

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 2
Source of Spectrum
EP-4664-0-0
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Spectrum
JZ-1992-3073-0
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2.2 LC-MS

1 of 17
View All
Authors
Taguchi R, Graduate School of Medicine, The University of Tokyo
Instrument
LC-10ADVPmicro HPLC, Shimadzu; LTQ Orbitrap, Thermo Scientific
Instrument Type
LC-ESI-ITFT
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
30%
Column Name
Develosil C30, Nomura Chemical
Retention Time
26.98 min (in paper: 26.9 min)
Precursor m/z
792.57
Precursor Adduct
[M+CH3COO]-
Top 5 Peaks

718.16 999

329.13 8

255.15 8

283.08 8

303.17 3

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License
CC BY-NC-SA
Reference
Taguchi, R.; Ishikawa, M. Precise and Global Identification of Phospholipid Molecular Species by an Orbitrap Mass Spectrometer and Automated Search Engine Lipid Search. Journal of Chromatography A 2010, 1217 (25), 4229-39. DOI:10.1016/j.chroma.2010.04.034
2 of 17
View All
Authors
Taguchi R, Graduate School of Medicine, The University of Tokyo
Instrument
LC-10ADVPmicro HPLC, Shimadzu; LTQ Orbitrap, Thermo Scientific
Instrument Type
LC-ESI-ITFT
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
30%
Column Name
Develosil C30, Nomura Chemical
Retention Time
27.03 min (in paper: 26.9 min)
Precursor m/z
792.58
Precursor Adduct
[M+CH3COO]-
Top 5 Peaks

718.16 999

255.09 7

733.08 6

718.85 3

480.06 2

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License
CC BY-NC-SA
Reference
Taguchi, R.; Ishikawa, M. Precise and Global Identification of Phospholipid Molecular Species by an Orbitrap Mass Spectrometer and Automated Search Engine Lipid Search. Journal of Chromatography A 2010, 1217 (25), 4229-39. DOI:10.1016/j.chroma.2010.04.034

4.2.3 Other MS

1 of 6
View All
MS Category
In-Silico
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
734.56998
Instrument
SCIEX 5600
Instrument Type
in-silico QTOF
Ionization Mode
positive
Collision Energy
45 V
Retention Time
5.52
Top 5 Peaks

184.0733 100

734.57 30.03

496.3405 5.01

478.3299 5.01

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2 of 6
View All
MS Category
In-Silico
MS Type
Other
MS Level
MS2
Precursor Type
[M+FA-H]-
Precursor m/z
778.55981
Instrument
SCIEX 5600
Instrument Type
in-silico QTOF
Ionization Mode
negative
Collision Energy
45 V
Retention Time
5.52
Top 5 Peaks

718.5387 100

255.2323 60.06

778.5598 20.02

224.0693 10.01

480.3092 5.01

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6 Chemical Vendors

7 Use and Manufacturing

7.1 Uses

Sources/Uses
A synthetic phospholipid used to study biological membranes; Also a major component of pulmonary surfactants; [ChemIDplus]

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 Hazards Summary

May cause irritation; [Aldrich MSDS] See Lecithin.

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Springer Nature References

9.4 Wiley References

9.5 Chemical Co-Occurrences in Literature

9.6 Chemical-Gene Co-Occurrences in Literature

9.7 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 WIPO PATENTSCOPE

10.3 Chemical Co-Occurrences in Patents

10.4 Chemical-Disease Co-Occurrences in Patents

10.5 Chemical-Gene Co-Occurrences in Patents

11 Biological Test Results

11.1 BioAssay Results

12 Taxonomy

A metabolome atlas of the aging mouse brain. Nat Commun. 2021 Oct 15;12(1):6021. DOI:10.1038/s41467-021-26310-y. PMID:34654818; PMCID:PMC8519999.
The Metabolome Atlas of the Aging Mouse Brain: https://mouse.atlas.metabolomics.us

13 Classification

13.1 MeSH Tree

13.2 ChemIDplus

13.3 NORMAN Suspect List Exchange Classification

13.4 EPA DSSTox Classification

13.5 MolGenie Organic Chemistry Ontology

14 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
    2,3-Bis(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate
    https://comptox.epa.gov/dashboard/DTXSID50910226
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    (4-oxido-10-oxo-7-palmitoyl-3,5,9-trioxa-4-phosphapentacosyl)trimethylammonium 4-oxide
    https://echa.europa.eu/substance-information/-/substanceinfo/100.018.322
    (±)-(4-oxido-10-oxo-7-palmitoyl-3,5,9-trioxa-4-phosphapentacosyl)trimethylammonium 4-oxide
    https://echa.europa.eu/substance-information/-/substanceinfo/100.018.664
  5. 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
  6. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
    1,2-Dipalmitoylphosphatidylcholine
    https://haz-map.com/Agents/10537
  7. 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
    1,2-Dipalmitoylphosphatidylcholine
    http://www.hmdb.ca/metabolites/HMDB0245715
  8. MassBank Europe
  9. 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
  10. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
    1,2-dipalmitoylphosphatidylcholine, DL-
    https://rxnav.nlm.nih.gov/id/rxnorm/1926947
  11. SpectraBase
    1,2-DI-O-HEXADECANOYL-3-O-[2-(TRIMETHYLAMINO)-ETHYL]-PHOSPHORYL)-RAC-GLYCEROL
    https://spectrabase.com/spectrum/JM9w37vMLNR
    3,5,9-Trioxa-4-phosphapentacosan-1-aminium, 4-hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-, hydroxide, inner salt, 4-oxide
    https://spectrabase.com/spectrum/9sSE2iFepbU
    3,5,9-Trioxa-4-phosphapentacosan-1-aminium, 4-hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-, hydroxide, inner salt, 4-oxide
    https://spectrabase.com/spectrum/D80KEvWakEa
  12. Springer Nature
  13. West Coast Metabolomics Center-UC Davis
    PC 32:0; PC 16:0_16:0;
  14. Wikidata
    DL-dipalmitoylphosphatidylcholine
    https://www.wikidata.org/wiki/Q2587934
  15. Wikipedia
  16. Wiley
  17. 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
    1,2-Dipalmitoylphosphatidylcholine
    https://www.ncbi.nlm.nih.gov/mesh/68015060
  18. PubChem
  19. 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/
  20. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  21. PATENTSCOPE (WIPO)
CONTENTS