Lactucin
PubChem CID
442266
Structure
Chemical Safety
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.
Chemical Structure Depiction
(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)
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)
VJQAFLAZRVKAKM-VZLIPTOUSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
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)
C15H16O5
Computed by PubChem 2.2 (PubChem release 2021.10.14)
81241-45-4
112-288-6
- 11beta,13-dihydrolactucin
- lactucin
- Lactucin
- Lactucine
- 1891-29-8
- VJQAFLAZRVKAKM-VZLIPTOUSA-
- R6E2918904
- (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
- (3aR,4S,9aS,9bR)-4-Hydroxy-9-(hydroxymethyl)-6-methyl-3-methylene-3,3a,4,5-tetrahydroazuleno[4,5-b]furan-2,7(9aH,9bH)-dione
- AC1L9CIQ
- UNII-R6E2918904
- LACTUCIN [MI]
- CHEBI:6358
- SCHEMBL14215975
- DTXSID70894751
- HY-N9438
- AKOS040763768
- FS-7317
- DA-64848
- CS-0169537
- NS00094051
- C09489
- (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
- (3aR,4S,9aS,9bR)-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
- (3aR,4S,9aS,9bR)-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
- Azuleno(4,5-b)furan-2,7-dione, 3,3a,4,5,9a,9b-hexahydro-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylene-, (3aR-(3aalpha,4beta,9aalpha,9bbeta))-
- InChI=1/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
Property Name
Property Value
Reference
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)
1D NMR Spectra
MoNA ID
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
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Parent, Connectivity Count
Similar Compounds (2D)
Similar Conformers (3D)
Same Count
Pictogram(s)
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.
Skin Sens. 1 (100%)
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
- CAS Common ChemistryLICENSEThe 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/
- ChemIDplusChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- EPA DSSToxCompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- European Chemicals Agency (ECHA)LICENSEUse 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-dionehttps://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
- FDA Global Substance Registration System (GSRS)LICENSEUnless 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
- ChEBI
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/LOTUS Treehttps://lotus.naturalproducts.net/
- Comparative Toxicogenomics Database (CTD)LICENSEIt 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
- Japan Chemical Substance Dictionary (Nikkaji)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlPhytochemical compoundshttp://www.genome.jp/kegg-bin/get_htext?br08003.keg
- Natural Product Activity and Species Source (NPASS)
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://creativecommons.org/licenses/by/4.0/LactucinNORMAN Suspect List Exchange Classificationhttps://www.norman-network.com/nds/SLE/
- MassBank of North America (MoNA)LICENSEThe content of the MoNA database is licensed under CC BY 4.0.https://mona.fiehnlab.ucdavis.edu/documentation/license
- Metabolomics Workbench
- NMRShiftDB
- SpectraBase
- Wikidata
- Wikipedia
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks 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
- GHS Classification (UNECE)GHS Classification Treehttp://www.unece.org/trans/danger/publi/ghs/ghs_welcome_e.html
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
CONTENTS