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Piperyline

PubChem CID
636537
Structure
Piperyline_small.png
Piperyline_3D_Structure.png
Piperyline__Crystal_Structure.png
Molecular Formula
Synonyms
  • Piperyline
  • Trichostachine
  • Trichostachin
  • Piperiline
  • Piperylin
Molecular Weight
271.31 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-01-18
Description
Piperyline is a N-acylpyrrolidine that is pyrollidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum. It has a role as a plant metabolite, an apoptosis inducer and an antifungal agent. It is a member of benzodioxoles, a N-acylpyrrolidine, a tertiary carboxamide and a pyrrolidine alkaloid. It is functionally related to an (E,E)-piperic acid.
Trichostachine has been reported in Piper arboreum, Piper amalago, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Piperyline.png

1.2 3D Conformer

1.3 Crystal Structures

COD Number
Associated Article
Ezawa, Toshinari; Inoue, Yutaka; Murata, Isamu; Suzuki, Mitsuaki; Takao, Koichi; Sugita, Yoshiaki; Kanamoto, Ikuo. Syntheses and crystal structures of two piperine derivatives. Acta Crystallographica Section E 2020;76(5):646-650. DOI: 10.1107/S2056989020004648
Crystal Structure Depiction
Crystal Structure Depiction
Hermann-Mauguin space group symbol
P b c a
Hall space group symbol
-P 2ac 2ab
Space group number
61
a
11.8747 Å
b
7.2485 Å
c
30.392 Å
α
90 °
β
90 °
γ
90 °
Z
8
Z'
1
Residual factor
0.1090

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-pyrrolidin-1-ylpenta-2,4-dien-1-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C16H17NO3/c18-16(17-9-3-4-10-17)6-2-1-5-13-7-8-14-15(11-13)20-12-19-14/h1-2,5-8,11H,3-4,9-10,12H2/b5-1+,6-2+
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

GQIJYUMTOUBHSH-IJIVKGSJSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1CCN(C1)C(=O)/C=C/C=C/C2=CC3=C(C=C2)OCO3
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C16H17NO3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

54976-54-4

2.3.2 UNII

2.3.3 ChEBI ID

2.3.4 ChEMBL ID

2.3.5 DSSTox Substance ID

2.3.6 HMDB ID

2.3.7 KEGG ID

2.3.8 Metabolomics Workbench ID

2.3.9 Nikkaji Number

2.3.10 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • (2E,4E)-5-(1,3-Benzodioxol-5-yl)-1-(1-pyrrolidinyl)-2,4-pentadien-1-one
  • 1-piperoylpyrrolidine
  • piperyline

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
271.31 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
3.1
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
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
271.12084340 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
271.12084340 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
38.8 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
399
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
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
2
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

Solid

3.2.2 Melting Point

143 - 145 °C

3.2.3 Kovats Retention Index

Semi-standard non-polar
2892.6 , 2803

3.3 SpringerMaterials Properties

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 7
View All
Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

201.0 99.99

271.0 79.70

172.0 19.40

272.0 19

200.0 17.50

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Notes
instrument=HITACHI M-80
2 of 7
View All
MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
HITACHI M-80
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

201 99.99

271 79.70

172 19.40

272 19

200 17.50

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License
CC BY-NC-SA

4.2.2 MS-MS

1 of 2
Spectra ID
Instrument Type
LC-ESI-qTof
Ionization Mode
Positive
Top 5 Peaks

201.055099 35664

135.044678 18408

115.05439 14016

143.049255 11536

171.044235 9536

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Notes
From GNPS Library
2 of 2
Spectra ID
Ionization Mode
positive
Top 5 Peaks

201.055099 100

135.044678 51.62

115.05439 39.30

143.049255 32.35

171.044235 26.74

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Notes
instrument=qTof

4.2.3 LC-MS

MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
272.12
Instrument
qTof
Ionization Mode
positive
Top 5 Peaks

201.055099 100

135.044678 51.62

115.054390 39.30

143.049255 32.35

171.044235 26.74

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6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Associated Foods

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Cellular Locations

Membrane

8.2 Biochemical Reactions

9 Toxicity

9.1 Toxicological Information

9.1.1 Acute Effects

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Thieme References

10.4 Chemical Co-Occurrences in Literature

10.5 Chemical-Gene Co-Occurrences in Literature

10.6 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

11.5 Chemical-Gene Co-Occurrences in Patents

12 Biological Test Results

12.1 BioAssay Results

13 Taxonomy

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

14 Classification

14.1 MeSH Tree

14.2 ChEBI Ontology

14.3 ChemIDplus

14.4 ChEMBL Target Tree

14.5 EPA DSSTox Classification

14.6 LOTUS Tree

14.7 MolGenie Organic Chemistry Ontology

15 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
    Pyrrolidine, 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-
    https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0054976544
    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. 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
  6. ChEBI
  7. 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/
  8. 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
  9. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  10. 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
  11. 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
  12. 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
    Pyrrolidine, 1-[5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-, (E,E)-
    http://www.nist.gov/srd/nist1a.cfm
  13. SpectraBase
    (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(1-pyrrolidinyl)-1-penta-2,4-dienone
    https://spectrabase.com/spectrum/B0rdI4LMuU8
    PIPERILINE;(2E,4E)-N-[5-(3',4'-METHYLENEDIOXY-PHENYL)-PENTA-2,4-DIENOYL]-PYRROLIDINE
    https://spectrabase.com/spectrum/DenMr4Uo98f
  14. Japan Chemical Substance Dictionary (Nikkaji)
  15. 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
  16. KNApSAcK Species-Metabolite Database
  17. Natural Product Activity and Species Source (NPASS)
  18. Metabolomics Workbench
  19. 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
  20. SpringerMaterials
  21. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  22. Wikidata
  23. PubChem
  24. 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
  25. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  26. PATENTSCOPE (WIPO)
CONTENTS