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CHEBI:66111 - jaspamide H

ChEBI IDCHEBI:66111
ChEBI Namejaspamide H
Stars
DefinitionA cyclodepsipeptide isolated from Jaspis splendens. A derivative of jaspamide, it has been shown to exhibit cytotoxic and microfilament disruption activity.
Last Modified13 April 2015
DownloadsMolfile
FormulaC35H43BrN4O6
Net Charge0
Average Mass695.655
Monoisotopic Mass694.23660
SMILES[H]C1/C=C(\C)C[C@H](C)C(=O)N[C@@H](C)C(=O)N(C)[C@H](Cc2c(Br)nc3ccccc23)C(=O)N[C@@H](c2ccc(O)cc2)CC(=O)O[C@@H](C)C1
InChIInChI=1S/C35H43BrN4O6/c1-20-9-8-10-22(3)46-31(42)19-29(24-13-15-25(41)16-14-24)39-34(44)30(18-27-26-11-6-7-12-28(26)38-32(27)36)40(5)35(45)23(4)37-33(43)21(2)17-20/h6-7,9,11-16,21-23,29-30,38,41H,8,10,17-19H2,1-5H3,(H,37,43)(H,39,44)/b20-9+/t21-,22-,23-,29+,30+/m0/s1
InChIKeyRDBNISBUPIBNGP-RAMWEYKWSA-N
Species of MetaboliteComponentSourceComments
Jaspis splendens (WORMS:169842) - DOI (10.1016/j.tet.2008.05.037)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
marine metabolite  Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
actin polymerisation inhibitor  Any substance that inhibits the polymerisation of the protein actin.
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)
jaspamide H (CHEBI:66111) has role actin polymerisation inhibitor (CHEBI:70728)
jaspamide H (CHEBI:66111) has role animal metabolite (CHEBI:75767)
jaspamide H (CHEBI:66111) has role antineoplastic agent (CHEBI:35610)
jaspamide H (CHEBI:66111) has role marine metabolite (CHEBI:76507)
jaspamide H (CHEBI:66111) is a cyclodepsipeptide (CHEBI:35213)
jaspamide H (CHEBI:66111) is a macrocycle (CHEBI:51026)
jaspamide H (CHEBI:66111) is a organobromine compound (CHEBI:37141)
IUPAC Name 
(4R,7R,10S,13S,15E,19S)-7-[(2-bromo-1H-indol-3-yl)methyl]-4-(4-hydroxyphenyl)-8,10,13,15,19-pentamethyl-1-oxa-5,8,11-triazacyclononadec-15-ene-2,6,9,12-tetrone