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CHEBI:177873 - grasshopper ketone
| Formula | C13H20O3 |
| Net Charge | 0 |
| Average Mass | 224.300 |
| Monoisotopic Mass | 224.14124 |
| SMILES | [H]C(=C=C1C(C)(C)C[C@H](O)C[C@@]1(C)O)C(C)=O |
| InChI | InChI=1S/C13H20O3/c1-9(14)5-6-11-12(2,3)7-10(15)8-13(11,4)16/h5,10,15-16H,7-8H2,1-4H3/t6-,10-,13+/m0/s1 |
| InChIKey | QMXLZUOHZGYGDY-ANSXDHORSA-N |
| Species of Metabolite | Component | Source | Comments |
|---|---|---|---|
| Aglaia silvestris (ncbitaxon:306516) | - | PubMed (15132542) | |
| Dysphania ambrosioides (ncbitaxon:330163) | - | PubMed (24761641) | Species also known as Chenopodium ambrosioides. |
| Murraya euchrestifolia (ncbitaxon:1224773) | - | PubMed (29090551) | |
| Oryza sativa (ncbitaxon:4530) | - | PubMed (22364828) | Isolated from the variety Awaakamai. |
| Romalea microptera (ncbitaxon:7007) | - | Article (Book: Blunt, JW and Munro, MHG. (2007) Dictionary of Marine Natural Products with CD-ROM. CRC Press, D-719.) | |
| Sargassum fulvellum (ncbitaxon:3016) | - | PubMed (30982318) | |
| Solanum lyratum (ncbitaxon:230192) | whole plant (BTO:0001461) | PubMed (24946547) | |
| Viola biflora (ncbitaxon:214529) | - | PubMed (30132649) | |
| Vitis vinifera (ncbitaxon:29760) | - | PubMed (12926890) | |
| Xanthium chinense (IPNI:269219-2) | fruit (BTO:0000486) | PubMed (29600618) |
| Roles Classification |
|---|
| Biological Roles: | phytotoxin Any toxin produced by a plant. animal metabolite Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals. algal metabolite Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae. marine metabolite Any metabolite produced during a metabolic reaction in marine macro- and microorganisms. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. |
| Application: | anti-inflammatory agent Any compound that has anti-inflammatory effects. |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| grasshopper ketone (CHEBI:177873) has role algal metabolite (CHEBI:84735) |
| grasshopper ketone (CHEBI:177873) has role animal metabolite (CHEBI:75767) |
| grasshopper ketone (CHEBI:177873) has role anti-inflammatory agent (CHEBI:67079) |
| grasshopper ketone (CHEBI:177873) has role marine metabolite (CHEBI:76507) |
| grasshopper ketone (CHEBI:177873) has role phytotoxin (CHEBI:38231) |
| grasshopper ketone (CHEBI:177873) has role plant metabolite (CHEBI:76924) |
| grasshopper ketone (CHEBI:177873) is a allenes (CHEBI:37602) |
| grasshopper ketone (CHEBI:177873) is a cyclohexanols (CHEBI:23480) |
| grasshopper ketone (CHEBI:177873) is a diol (CHEBI:23824) |
| grasshopper ketone (CHEBI:177873) is a enone (CHEBI:51689) |
| grasshopper ketone (CHEBI:177873) is a methyl ketone (CHEBI:51867) |
| grasshopper ketone (CHEBI:177873) is a secondary alcohol (CHEBI:35681) |
| grasshopper ketone (CHEBI:177873) is a tertiary allylic alcohol (CHEBI:134397) |
| IUPAC Name |
|---|
| (3Ra)-4-[(2R,4S)-2,4-dihydroxy-2,6,6-trimethylcyclohexylidene]but-3-en-2-one |
| Synonyms | Source |
|---|---|
| (3M)-4-[(2R,4S)-2,4-dihydroxy-2,6,6-trimethylcyclohexylidene]but-3-en-2-one | IUPAC |
| (−)-grasshopper ketone | KNApSAcK |
| Citations |
|---|