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CHEBI:66586 - (7Z)-lobohedleolide

ChEBI IDCHEBI:66586
ChEBI Name(7Z)-lobohedleolide
Stars
ASCII Name(7Z)-lobohedleolide
DefinitionA cembrane diterpenoid isolated from Lobophytum hedleyi and Lobophytum. It exhibits anti-HIV-1 activity.
Last Modified1 October 2014
DownloadsMolfile
FormulaC20H26O4
Net Charge0
Average Mass330.424
Monoisotopic Mass330.18311
SMILES[H][C@@]12CC/C(C)=C/CC/C(C(=O)O)=C/CC/C(C)=C/[C@]1([H])OC(=O)C2=C
InChIInChI=1S/C20H26O4/c1-13-6-4-8-16(19(21)22)9-5-7-14(2)12-18-17(11-10-13)15(3)20(23)24-18/h6,9,12,17-18H,3-5,7-8,10-11H2,1-2H3,(H,21,22)/b13-6+,14-12+,16-9-/t17-,18-/m0/s1
InChIKeySORYERHBQFTRIK-JMQTVVQQSA-N
Species of MetaboliteComponentSourceComments
Lobophytum (ncbitaxon:205095) - PubMed (10785433) Aqueous extract
Lobophytum hedleyi (WORMS:292556) - DOI (10.1016/S0040-4039(01)82073-6)
Roles Classification
Chemical Role:
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)
(7Z)-lobohedleolide (CHEBI:66586) has role anti-HIV-1 agent (CHEBI:64947)
(7Z)-lobohedleolide (CHEBI:66586) has role coral metabolite (CHEBI:76498)
(7Z)-lobohedleolide (CHEBI:66586) is a cembrane diterpenoid (CHEBI:60687)
(7Z)-lobohedleolide (CHEBI:66586) is a monocarboxylic acid (CHEBI:25384)
(7Z)-lobohedleolide (CHEBI:66586) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(3aS,6E,10Z,14E,15aS)-6,14-dimethyl-3-methylidene-2-oxo-2,3,3a,4,5,8,9,12,13,15a-decahydrocyclotetradeca[b]furan-10-carboxylic acid
Registry NumbersSources
Reaxys:4709575Reaxys
Citations