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CHEBI:66104 - jaspamide

Default Structure
ChEBI IDCHEBI:66104
ChEBI Namejaspamide
Stars
DefinitionA cyclodepsipeptide isolated from Jaspis splendens and has been shown to exhibit antineoplastic activity. It is an actin polymerization and stabilization inducer.
Last Modified11 June 2021
DownloadsMolfile
FormulaC36H45BrN4O6
Net Charge0
Average Mass709.682
Monoisotopic Mass708.25225
SMILESC/C1=C\[C@H](C)C[C@H](C)OC(=O)C[C@H](c2ccc(O)cc2)NC(=O)[C@@H](Cc2c(Br)nc3ccccc23)N(C)C(=O)[C@H](C)NC(=O)[C@@H](C)C1
InChIInChI=1S/C36H45BrN4O6/c1-20-15-21(2)17-23(4)47-32(43)19-30(25-11-13-26(42)14-12-25)40-35(45)31(18-28-27-9-7-8-10-29(27)39-33(28)37)41(6)36(46)24(5)38-34(44)22(3)16-20/h7-15,21-24,30-31,39,42H,16-19H2,1-6H3,(H,38,44)(H,40,45)/b20-15+/t21-,22-,23-,24-,30+,31+/m0/s1
InChIKeyGQWYWHOHRVVHAP-DHKPLNAMSA-N
Species of MetaboliteComponentSourceComments
Jaspis splendens (WORMS:169842)
- DOI (10.1016/j.tet.2008.05.037)
- PubMed (21241058) Methanolic extract of sponge
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
actin polymerisation inducer  Any substance that induces the polymerisation of the protein actin.
marine metabolite  Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
animal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
ChEBI Ontology
Outgoing Relation(s)
jaspamide (CHEBI:66104) has role actin polymerisation inducer (CHEBI:176495)
jaspamide (CHEBI:66104) has role animal metabolite (CHEBI:75767)
jaspamide (CHEBI:66104) has role antifungal agent (CHEBI:35718)
jaspamide (CHEBI:66104) has role antineoplastic agent (CHEBI:35610)
jaspamide (CHEBI:66104) has role apoptosis inducer (CHEBI:68495)
jaspamide (CHEBI:66104) has role marine metabolite (CHEBI:76507)
jaspamide (CHEBI:66104) has role neuroprotective agent (CHEBI:63726)
jaspamide (CHEBI:66104) is a cyclodepsipeptide (CHEBI:35213)
jaspamide (CHEBI:66104) is a phenols (CHEBI:33853)
IUPAC Name 
(4R,7R,10S,13S,15E,17R,19S)-7-[(2-bromo-1H-indol-3-yl)methyl]-4-(4-hydroxyphenyl)-8,10,13,15,17,19-hexamethyl-1-oxa-5,8,11-triazacyclononadec-15-ene-2,6,9,12-tetrone
Synonyms  Source
beta-Alanine, N-(2-bromo-N-(N-(8-hydroxy-2,4,6-trimethyl-1-oxo-4-nonenyl)-L-alanyl)-N-methyl-D-tryptophyl)-L-3-(4-hydroxyphenyl)-, p-lactone, (2S-(2R*,4E,6S*,8R*))-ChemIDplus
JaspamideChemIDplus
(+)-JasplakinolideKNApSAcK
JasplakinolideChemIDplus
Manual XrefsDatabases
C00026975KNApSAcK
C16883KEGG COMPOUND
KR20030085421Patent
Registry NumbersSources
Reaxys:4649870Reaxys
CAS:102396-24-7ChemIDplus
CAS:102396-24-7KEGG COMPOUND
Citations