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CHEBI:66587 - 17-dimethylaminolobohedleolide

ChEBI IDCHEBI:66587
ChEBI Name17-dimethylaminolobohedleolide
Stars
DefinitionA cembrane diterpenoid isolated from Lobophytum and shown to have anti-HIV-1 activity.
Last Modified1 October 2014
DownloadsMolfile
FormulaC22H33NO4
Net Charge0
Average Mass375.509
Monoisotopic Mass375.24096
SMILES[H][C@@]12CC/C(C)=C/CC/C(C(=O)O)=C/CC/C(C)=C/[C@]1([H])OC(=O)[C@H]2CN(C)C
InChIInChI=1S/C22H33NO4/c1-15-7-5-9-17(21(24)25)10-6-8-16(2)13-20-18(12-11-15)19(14-23(3)4)22(26)27-20/h7,10,13,18-20H,5-6,8-9,11-12,14H2,1-4H3,(H,24,25)/b15-7+,16-13+,17-10-/t18-,19-,20-/m0/s1
InChIKeyHRPBIJBOFQXOTL-JEJSWHNFSA-N
Species of MetaboliteComponentSourceComments
Lobophytum (ncbitaxon:205095) - PubMed (10785433) Aqueous extract
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
anti-HIV-1 agent  An anti-HIV agent that destroys or inhibits the replication of HIV-1, the more infective and more virulent of the two types of HIV virus.
coral metabolite  Any animal metabolite produced during a metabolic reaction in corals (marine invertebrates).
ChEBI Ontology
Outgoing Relation(s)
17-dimethylaminolobohedleolide (CHEBI:66587) has role anti-HIV-1 agent (CHEBI:64947)
17-dimethylaminolobohedleolide (CHEBI:66587) has role coral metabolite (CHEBI:76498)
17-dimethylaminolobohedleolide (CHEBI:66587) is a cembrane diterpenoid (CHEBI:60687)
17-dimethylaminolobohedleolide (CHEBI:66587) is a monocarboxylic acid (CHEBI:25384)
17-dimethylaminolobohedleolide (CHEBI:66587) is a tertiary amine (CHEBI:32876)
17-dimethylaminolobohedleolide (CHEBI:66587) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(3R,3aS,6E,10E,14E,15aR)-3-[(dimethylamino)methyl]-6,14-dimethyl-2-oxo-2,3,3a,4,5,8,9,12,13,15a-decahydrocyclotetradeca[b]furan-10-carboxylic acid
Registry NumbersSources
Reaxys:8589733Reaxys
Citations