| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:06:05 UTC |
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| Update date | 2019-11-26 02:59:49 UTC |
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| Primary ID | FDB004114 |
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| Secondary Accession Numbers | |
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| Chemical Information |
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| FooDB Name | Lappaphen A |
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| Description | Lappaphen b belongs to guaianolides and derivatives class of compounds. Those are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Lappaphen b is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Lappaphen b can be found in burdock, which makes lappaphen b a potential biomarker for the consumption of this food product. |
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| CAS Number | Not Available |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C27H26O4S2 |
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| IUPAC name | 3-hydroxy-6,9-dimethylidene-3-(2-oxo-2-{5-[5-(prop-1-yn-1-yl)thiophen-2-yl]thiophen-2-yl}ethyl)-dodecahydroazuleno[4,5-b]furan-2-one |
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| InChI Identifier | InChI=1S/C27H26O4S2/c1-4-5-17-8-11-22(32-17)23-13-12-21(33-23)20(28)14-27(30)19-10-7-15(2)18-9-6-16(3)24(18)25(19)31-26(27)29/h8,11-13,18-19,24-25,30H,2-3,6-7,9-10,14H2,1H3 |
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| InChI Key | WKQBNYGTPIGLMV-UHFFFAOYSA-N |
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| Isomeric SMILES | CC#CC1=CC=C(S1)C1=CC=C(S1)C(=O)CC1(O)C2CCC(=C)C3CCC(=C)C3C2OC1=O |
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| Average Molecular Weight | 478.623 |
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| Monoisotopic Molecular Weight | 478.1272507 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Terpene lactones |
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| Direct Parent | Guaianolides and derivatives |
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| Alternative Parents | |
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| Substituents | - Guaianolide-skeleton
- Guaiane sesquiterpenoid
- Sesquiterpenoid
- Bithiophene
- Aryl alkyl ketone
- Aryl ketone
- 2,5-disubstituted thiophene
- Beta-hydroxy ketone
- Gamma butyrolactone
- Heteroaromatic compound
- Thiophene
- Tetrahydrofuran
- Tertiary alcohol
- Carboxylic acid ester
- Ketone
- Lactone
- Organoheterocyclic compound
- Oxacycle
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Alcohol
- Carbonyl group
- Organic oxide
- Organic oxygen compound
- Organooxygen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | Not Available |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-003r-0780900000-f8ffe9ab99797097a190 | 2016-06-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0032-0492200000-9513075fd98f4bf8ddd3 | 2016-06-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-114i-3910000000-aca51fa4c3358fdc9138 | 2016-06-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-003r-0390800000-33150cacde799305f364 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001j-0892300000-831ab524f10896f24f2f | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0019-9401000000-4ab4d05f5996f5860dd6 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0010900000-8f247be1aeb8ae833b3e | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0091000000-ffab6357ec96d17b6957 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-9842400000-48d4ed9ddad9ea9f8a73 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0000900000-9f11197be8137d46ec75 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0059-0151900000-1b6645bca0a44c9ef32e | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0r01-1980000000-6bc012a66cfd2c16ed55 | 2021-10-21 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | Not Available |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | Not Available |
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| Pubchem Compound ID | Not Available |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | Not Available |
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| CRC / DFC (Dictionary of Food Compounds) ID | JWG93-Y:JWG93-Y |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | LAPPAPHEN-A |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | Not Available |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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