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Lactucin

PubChem CID
442266
Structure
Lactucin_small.png
Lactucin_3D_Structure.png
Molecular Formula
Synonyms
  • Lactucin
  • Lactucine
  • 1891-29-8
  • VJQAFLAZRVKAKM-VZLIPTOUSA-
  • R6E2918904
Molecular Weight
276.28 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-06-24
  • Modify:
    2025-01-25
Description
Lactucin is an azulenofuran that is 3-methylidene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione carrying additional hydroxy, methyl and hydroxymethyl substituents at positions 4, 6 and 9 respectively (the 3aR,4S,9aS,9bR-diastereomer). Found in chicory. It has a role as an antimalarial, a sedative and a plant metabolite. It is a sesquiterpene lactone, an azulenofuran, a cyclic terpene ketone, an enone, a primary alcohol and a secondary alcohol.
Lactucin has been reported in Lactuca saligna, Picris hieracioides, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Lactucin.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3aR,4S,9aS,9bR)-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C15H16O5/c1-6-3-9(17)12-7(2)15(19)20-14(12)13-8(5-16)4-10(18)11(6)13/h4,9,12-14,16-17H,2-3,5H2,1H3/t9-,12+,13-,14-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

VJQAFLAZRVKAKM-VZLIPTOUSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC1=C2[C@@H]([C@@H]3[C@@H]([C@H](C1)O)C(=C)C(=O)O3)C(=CC2=O)CO
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C15H16O5
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 Deprecated CAS

81241-45-4

2.3.3 European Community (EC) Number

112-288-6

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 DSSTox Substance ID

2.3.7 KEGG ID

2.3.8 Metabolomics Workbench ID

2.3.9 Nikkaji Number

2.3.10 Wikidata

2.3.11 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 11beta,13-dihydrolactucin
  • lactucin

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
276.28 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-0.7
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
276.09977361 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
276.09977361 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
83.8 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
583
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
4
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)

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 13C NMR Spectra

1 of 2
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 LC-MS

MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
277.108
Instrument
qTof
Ionization Mode
positive
Top 5 Peaks

213.090607 100

185.095673 92.79

241.085464 34.62

277.106537 26.55

157.100845 26.35

Thumbnail
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6 Chemical Vendors

7 Safety and Hazards

7.1 Hazards Identification

7.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
Precautionary Statement Codes

P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

7.1.2 Hazard Classes and Categories

Skin Sens. 1 (100%)

8 Associated Disorders and Diseases

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Chemical Co-Occurrences in Literature

9.4 Chemical-Gene Co-Occurrences in Literature

9.5 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 Chemical Co-Occurrences in Patents

10.3 Chemical-Disease Co-Occurrences in Patents

10.4 Chemical-Gene Co-Occurrences in Patents

11 Interactions and Pathways

11.1 Chemical-Target Interactions

12 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
S29 | PHYTOTOXINS | Toxic Plant Phytotoxin (TPPT) Database | DOI:10.5281/zenodo.2652993

13 Classification

13.1 MeSH Tree

13.2 ChEBI Ontology

13.3 KEGG: Phytochemical Compounds

13.4 ChemIDplus

13.5 UN GHS Classification

13.6 NORMAN Suspect List Exchange Classification

13.7 EPA DSSTox Classification

13.8 LOTUS Tree

13.9 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
    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
    (3aR,4S,9aS,9bR)-3,3a,4,5,9a,9b-Hexahydro-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methyleneazuleno[4,5-b]furan-2,7-dione
    https://echa.europa.eu
    (3aR,4S,9aS,9bR)-3,3a,4,5,9a,9b-Hexahydro-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methyleneazuleno[4,5-b]furan-2,7-dione (EC: 112-288-6)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/398260
  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. 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. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  9. Japan Chemical Substance Dictionary (Nikkaji)
  10. 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
  11. Natural Product Activity and Species Source (NPASS)
  12. 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/
    Lactucin
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  13. 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
  14. Metabolomics Workbench
  15. NMRShiftDB
  16. SpectraBase
  17. Wikidata
  18. Wikipedia
  19. PubChem
  20. 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
  21. GHS Classification (UNECE)
  22. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS