CHEBI:177873 - grasshopper ketone

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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 0
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.
View more via ChEBI Ontology
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
(3Ra)-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
Manual Xrefs Databases
10200510 ChemSpider
C00031831 KNApSAcK
CPD-7201 MetaCyc
FDB013523 FooDB
View more database links
Registry Number Type Source
41703-38-2 CAS Registry Number KNApSAcK
Citations Waiting for Citations Types Sources
12926890 PubMed citation Europe PMC
15132542 PubMed citation Europe PMC
22364828 PubMed citation Europe PMC
22530677 PubMed citation Europe PMC
24761641 PubMed citation Europe PMC
24946547 PubMed citation Europe PMC
27608302 PubMed citation Europe PMC
29090551 PubMed citation Europe PMC
29600618 PubMed citation Europe PMC
30132649 PubMed citation Europe PMC
30982318 PubMed citation Europe PMC
IND20419195 Agricola citation Europe PMC
IND20511662 Agricola citation Europe PMC
Last Modified
19 August 2021