grasshopper ketone (CHEBI:177873)

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ChEBI Name	grasshopper ketone

ChEBI ID	CHEBI:177873

Definition	A member of the class of allenes that is cyclohexane substituted by 3-oxobut-1-en-1-ylidene, methyl, hydroxy, hydroxy, methyl and methyl groups at positions 1, 2, 2, 4, 6 and 6, respectively (the 2R,3R,4S-stereoisomer). It is isolated from the grasshopper, Romalea microptera.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Bijay

Supplier Information

Download	Molfile XML SDF

Formula

C13H20O3

Net Charge

Average Mass

224.300

Monoisotopic Mass

224.14124

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

SMILES

[H]C(=[C@@]=C1C(C)(C)C[C@H](O)C[C@@]1(C)O)C(C)=O

Metabolite of Species	Details
Xanthium chinense (IPNI:269219-2)	Found in fruit (BTO:0000486). See: PubMed
Murraya euchrestifolia (NCBI:txid1224773)	See: PubMed
Viola biflora (NCBI:txid214529)	See: PubMed
Solanum lyratum (NCBI:txid230192)	Found in whole plant (BTO:0001461). See: PubMed
Vitis vinifera (NCBI:txid29760)	See: PubMed
Sargassum fulvellum (NCBI:txid3016)	See: PubMed
Aglaia silvestris (NCBI:txid306516)	See: PubMed
Dysphania ambrosioides (NCBI:txid330163)	Species also known as Chenopodium ambrosioides. See: PubMed
Oryza sativa (NCBI:txid4530)	Isolated from the variety Awaakamai. See: PubMed
Romalea microptera (NCBI:txid7007)	See: Book: Blunt, JW and Munro, MHG. (2007) Dictionary of Marine Natural Products with CD-ROM. CRC Press, D-719.

Roles Classification
Biological Role(s):	phytotoxin Any toxin produced by a plant. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. 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. animal metabolite Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.

Application(s):	anti-inflammatory agent Any compound that has anti-inflammatory effects.

ChEBI Ontology
Outgoing	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

(3R_a)-4-[(2R,4S)-2,4-dihydroxy-2,6,6-trimethylcyclohexylidene]but-3-en-2-one

Synonyms	Sources
(−)-grasshopper ketone	KNApSAcK
(3M)-4-[(2R,4S)-2,4-dihydroxy-2,6,6-trimethylcyclohexylidene]but-3-en-2-one	IUPAC

Registry Number	Type	Source
41703-38-2	CAS Registry Number	KNApSAcK

Last Modified

19 August 2021