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CHEBI:69134 - laulimalide

ChEBI IDCHEBI:69134
ChEBI Namelaulimalide
Stars
DefinitionA macrolide with formula C30H42O7 that is isolated from the marine sponges, Cacospongia mycofijiensis and Hyattella sp.
Last Modified18 October 2021
DownloadsMolfile
FormulaC30H42O7
Net Charge0
Average Mass514.659
Monoisotopic Mass514.29305
SMILES[H][C@]12CC=C[C@@]([H])(C/C=C\C(=O)O[C@H]([C@@H](O)/C=C/[C@]3([H])CC(C)=CCO3)C[C@]3([H])O[C@@]3([H])[C@@H](O)CC(=C)C[C@H](C)C1)O2
InChIInChI=1S/C30H42O7/c1-19-12-13-34-23(15-19)10-11-25(31)27-18-28-30(37-28)26(32)17-21(3)14-20(2)16-24-8-4-6-22(35-24)7-5-9-29(33)36-27/h4-6,9-12,20,22-28,30-32H,3,7-8,13-18H2,1-2H3/b9-5-,11-10+/t20-,22-,23+,24-,25-,26-,27-,28-,30-/m0/s1
InChIKeyMSBQEQDLFWWWMV-XZZGLLCESA-N
Species of MetaboliteComponentSourceComments
Cacospongia mycofijiensis (ncbitaxon:1162744) - DOI (10.1021/jo00250a052) Species also known as Spongia mycofijiensis.
Fasciospongia rimosa (ncbitaxon:572251) - DOI (10.1021/ja0027416)
Hyattella Sp. (ncbitaxon:436463) - DOI (10.1021/ja0027416)
Roles Classification
Biological Roles:
microtubule-stabilising agent  Any substance that interacts with tubulin to promote polymerisation of microtubules.
marine metabolite  Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
antimitotic  Any compound that inhibits cell division (mitosis).
animal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
laulimalide (CHEBI:69134) has role animal metabolite (CHEBI:75767)
laulimalide (CHEBI:69134) has role antimitotic (CHEBI:64911)
laulimalide (CHEBI:69134) has role antineoplastic agent (CHEBI:35610)
laulimalide (CHEBI:69134) has role marine metabolite (CHEBI:76507)
laulimalide (CHEBI:69134) has role microtubule-stabilising agent (CHEBI:61950)
laulimalide (CHEBI:69134) is a carboxylic ester (CHEBI:33308)
laulimalide (CHEBI:69134) is a epoxide (CHEBI:32955)
laulimalide (CHEBI:69134) is a macrolide (CHEBI:25106)
laulimalide (CHEBI:69134) is a secondary alcohol (CHEBI:35681)
laulimalide (CHEBI:69134) is a secondary allylic alcohol (CHEBI:134396)
IUPAC Name 
(1R,3S,7S,8S,10S,12S,15Z,18R)-7-hydroxy-12-{(1S,2E)-1-hydroxy-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]prop-2-en-1-yl}-3-methyl-5-methylidene-9,13,22-trioxatricyclo[16.3.1.08,10]docosa-15,19-dien-14-one
Synonyms  Source
(−)-laulimalideChEBI
fijianolide BChEBI
(1R,3S,7S,8S,10S,12S,15Z,18R)-12-[(1S,2E)-3-[(2S)-3,6-dihydro-4-methyl-2H-pyran-2-yl]-1-hydroxy-2-propen-1-yl]-7-hydroxy-3-methyl-5-methylene-9,13,22-trioxatricyclo[16.3.1.08,10]docosa-15,19-dien-14-oneChEBI
Manual XrefsDatabases
C00044855KNApSAcK
WO2008112799Patent
Registry NumbersSources
CAS:115268-43-4ChEBI
Citations