EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:176569 - brachialactone

ChEBI IDCHEBI:176569
ChEBI Namebrachialactone
Stars
DefinitionA tetracyclic diterpenoid with formula C20H30O4. It is a nitrification inhibitor isolated from root exudates of Brachiaria humidicola.
Last Modified22 June 2021
DownloadsMolfile
FormulaC20H30O4
Net Charge0
Average Mass334.456
Monoisotopic Mass334.21441
SMILES[H][C@]12C[C@@]3(C)CC[C@H](C(C)C)[C@]3([H])C/C=C3/C(=O)O[C@]([H])(C[C@]31[H])[C@]2(O)CO
InChIInChI=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
InChIKeyGWNHAMYTHQFCMC-AAUVUIHKSA-N
Species of MetaboliteComponentSourceComments
Brachiaria humidicola (ncbitaxon:240451) - PubMed (32663650) Identified in root exudates.
Roles Classification
Biological Roles:
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.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
brachialactone (CHEBI:176569) has role nitrification inhibitor (CHEBI:148436)
brachialactone (CHEBI:176569) has role plant metabolite (CHEBI:76924)
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)
brachialactone (CHEBI:176569) is a δ-lactone (CHEBI:18946)
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