CHEBI:69134 - laulimalide

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ChEBI Name laulimalide
ChEBI ID CHEBI:69134
Definition A macrolide with formula C30H42O7 that is isolated from the marine sponges, Cacospongia mycofijiensis and Hyattella sp.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H42O7
Net Charge 0
Average Mass 514.659
Monoisotopic Mass 514.29305
InChI InChI=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
InChIKey MSBQEQDLFWWWMV-XZZGLLCESA-N
SMILES [H][C@]12C[C@H](OC(=O)\C=C/C[C@@]3([H])O[C@@]([H])(CC=C3)C[C@@H](C)CC(=C)C[C@H](O)[C@]1([H])O2)[C@@H](O)\C=C\[C@]1([H])CC(C)=CCO1
Metabolite of Species Details
Cacospongia mycofijiensis (NCBI:txid1162744) Species also known as Spongia mycofijiensis. See: DOI
Hyattella Sp. (NCBI:txid436463) See: DOI
Fasciospongia rimosa (NCBI:txid572251) See: DOI
Roles Classification
Biological Role(s): microtubule-stabilising agent
Any substance that interacts with tubulin to promote polymerisation of microtubules.
antimitotic
Any compound that inhibits cell division (mitosis).
marine metabolite
Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
animal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
(−)-laulimalide ChEBI
(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-one ChEBI
fijianolide B ChEBI
Manual Xrefs Databases
C00044855 KNApSAcK
WO2008112799 Patent
View more database links
Registry Number Type Source
115268-43-4 CAS Registry Number ChEBI
Citations Waiting for Citations Types Sources
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Last Modified
18 October 2021