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Pinolenic acid

PubChem CID
5312495
Structure
Pinolenic acid_small.png
Pinolenic acid_3D_Structure.png
Molecular Formula
Synonyms
  • Pinolenic acid
  • 16833-54-8
  • (5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid
  • 5Z,9Z,12Z-octadecatrienoic acid
  • Pinolenic acid [MI]
Molecular Weight
278.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2006-01-13
  • Modify:
    2025-01-04
Description
(5Z,9Z,12Z)-octadecatrienoic acid is an octadecatrienoic acid having three double bonds located at positions 5, 9 and 12 (the all-cis-isomer). It has a role as a plant metabolite and an antineoplastic agent.
Pinolenic acid has been reported in Teucrium cubense and Pinus koraiensis with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Pinolenic acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,13-14H,2-5,8,11-12,15-17H2,1H3,(H,19,20)/b7-6-,10-9-,14-13-
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

HXQHFNIKBKZGRP-URPRIDOGSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCCCC/C=C\C/C=C\CC/C=C\CCCC(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C18H30O2
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 DSSTox Substance ID

2.3.5 Lipid Maps ID (LM_ID)

2.3.6 Metabolomics Workbench ID

2.3.7 Wikidata

2.3.8 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 5,9,12-octadecatrienoic acid
  • 5,9,12-octadecatrienoic acid, (cis)-isomer
  • 5,9,12-octadecatrienoic acid, (Z,Z,E)-isomer
  • columbinic acid
  • pinolenic acid
  • trans-5,9,12-octadecatrienoic acid

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
278.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
5.6
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
13
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
278.224580195 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
278.224580195 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
37.3Ų
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
301
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
3
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 Chemical Classes

3.2.1 Endocrine Disruptors

Potential endocrine disrupting compound
S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198

3.2.2 Lipids

Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 MS-MS

1 of 2
NIST Number
1208104
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M-H]-
Precursor m/z
277.2173
Total Peaks
30
m/z Top Peak
233.2
m/z 2nd Highest
259.2
m/z 3rd Highest
275.2
Thumbnail
Thumbnail
2 of 2
NIST Number
1212928
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
279.2319
Total Peaks
74
m/z Top Peak
261.3
m/z 2nd Highest
243.3
m/z 3rd Highest
181.1
Thumbnail
Thumbnail

4.1.2 LC-MS

1 of 8
View All
Accession ID
Authors
Plant Biology, The Noble Foundation, Ardmore, OK, US/Dennis Fine, Daniel Wherritt, and Lloyd Sumner
Instrument
Bruker impact HD
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
10 eV
Column Name
Waters Acquity BEH C18 1.7um x 2.1 x 150 mm
Retention Time
1705.8 sec
Precursor m/z
277.2183
Precursor Adduct
[M-H]-
Top 5 Peaks

277.2183 999

278.2213 152

Thumbnail
Thumbnail
License
CC BY-NC-SA
2 of 8
View All
Accession ID
Authors
Plant Biology, The Noble Foundation, Ardmore, OK, US/Dennis Fine, Daniel Wherritt, and Lloyd Sumner
Instrument
Bruker impact HD
Instrument Type
LC-ESI-QTOF
MS Level
MS
Ionization Mode
NEGATIVE
Ionization
ESI
Column Name
Waters Acquity BEH C18 1.7um x 2.1 x 150 mm
Retention Time
1705.8 sec
Top 5 Peaks

277.2182 999

278.2213 184

345.2055 116

556.0034 90

577.426 66

Thumbnail
Thumbnail
License
CC BY-NC-SA

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Biochemical Reactions

8 Literature

8.1 Consolidated References

8.2 NLM Curated PubMed Citations

8.3 Springer Nature References

8.4 Chemical Co-Occurrences in Literature

8.5 Chemical-Gene Co-Occurrences in Literature

8.6 Chemical-Disease Co-Occurrences in Literature

9 Patents

9.1 Depositor-Supplied Patent Identifiers

9.2 WIPO PATENTSCOPE

9.3 Chemical Co-Occurrences in Patents

9.4 Chemical-Disease Co-Occurrences in Patents

9.5 Chemical-Gene Co-Occurrences in Patents

10 Interactions and Pathways

10.1 Pathways

11 Biological Test Results

11.1 BioAssay Results

12 Taxonomy

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

13 Classification

13.1 MeSH Tree

13.2 ChEBI Ontology

13.3 LIPID MAPS Classification

13.4 ChemIDplus

13.5 EPA DSSTox Classification

13.6 LOTUS Tree

13.7 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
    cis,cis,cis-5,9,12-Octadecatrienoic acid
    https://comptox.epa.gov/dashboard/DTXSID00895852
    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. ChEBI
  6. 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/
  7. KNApSAcK Species-Metabolite Database
  8. Natural Product Activity and Species Source (NPASS)
  9. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  10. MassBank Europe
  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. Metabolomics Workbench
  13. 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
  14. 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/
  15. Springer Nature
  16. Wikidata
  17. Wikipedia
  18. PubChem
  19. 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
    5,9,12-octadecatrienoic acid
    https://www.ncbi.nlm.nih.gov/mesh/67034302
  20. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  21. PATENTSCOPE (WIPO)
CONTENTS