CHEBI:176569 - brachialactone

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ChEBI Name brachialactone
ChEBI ID CHEBI:176569
Definition A tetracyclic diterpenoid with formula C20H30O4. It is a nitrification inhibitor isolated from root exudates of Brachiaria humidicola.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Supplier Information
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Formula C20H30O4
Net Charge 0
Average Mass 334.456
Monoisotopic Mass 334.21441
InChI InChI=1S/C20H30O4/c1-11(2)12-6-7-19(3)9-16-14-8-17(20(16,23)10-21)24-18(22)13(14)4-5-15(12)19/h4,11-12,14-17,21,23H,5-10H2,1-3H3/b13-4+/t12-,14-,15+,16+,17-,19-,20+/m1/s1
InChIKey GWNHAMYTHQFCMC-AAUVUIHKSA-N
SMILES [H][C@@]12C[C@]3([H])\C(=C/C[C@@]4([H])[C@H](CC[C@]4(C)C[C@]3([H])[C@@]1(O)CO)C(C)C)C(=O)O2
Metabolite of Species Details
Brachiaria humidicola (NCBI:txid240451) Identified in root exudates. See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
nitrification inhibitor
Any inhibitor added to nitrogen fertilizers which can reduce the rate at which ammonium is converted to nitrate. Under appropriate conditions, this can help reduce nitrogen losses through denitrification and leaching.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing brachialactone (CHEBI:176569) has role nitrification inhibitor (CHEBI:148436)
brachialactone (CHEBI:176569) has role plant metabolite (CHEBI:76924)
brachialactone (CHEBI:176569) is a δ-lactone (CHEBI:18946)
brachialactone (CHEBI:176569) is a primary alcohol (CHEBI:15734)
brachialactone (CHEBI:176569) is a tertiary alcohol (CHEBI:26878)
brachialactone (CHEBI:176569) is a tetracyclic diterpenoid (CHEBI:52557)
IUPAC Name
[3R,4aS,5S,6aR,9R,9aS,11(11a)E,12R]-12-hydroxy-12-(hydroxymethyl)-6a-methyl-9-(propan-2-yl)-4,4a,5,6,6a,7,8,9,9a,10-decahydro-3,5-methanocyclopenta[5,6]cycloocta[1,2-c]pyran-1(3H)-one
Citations Waiting for Citations Types Sources
19805171 PubMed citation Europe PMC
23118123 PubMed citation Europe PMC
32663650 PubMed citation Europe PMC
Last Modified
22 June 2021