CHEBI:157684 - lymphostin

ChEBI IDCHEBI:157684
ChEBI Namelymphostin
Stars
DefinitionA member of the class of pyrroloquinolines that is pyrrolo[4,3,2-de]quinoline in which the hydrogens at positions 4, 6 and 8 are replaced by (1E)-1-methoxy-3-oxoprop-1-en-3-yl, acetylamino and amino groups, respectively. It is an alkaloid isolated from Streptomyces and Salinispora species, exhibits potent immunosuppressive activity, and inhibits Fyn and Lck protein kinases.
Last Modified9 November 2020
SubmitterMartin Larralde
DownloadsMolfile
FormulaC16H14N4O3
Net Charge0
Average Mass310.313
Monoisotopic Mass310.10659
SMILESCO/C=C/C(=O)c1cc2c3c(c(N)cc(NC(C)=O)c3n1)N=C2
InChIInChI=1S/C16H14N4O3/c1-8(21)19-12-6-10(17)15-14-9(7-18-15)5-11(20-16(12)14)13(22)3-4-23-2/h3-7H,17H2,1-2H3,(H,19,21)/b4-3+
InChIKeyHQPIKMNKCMXJQC-ONEGZZNKSA-N
Species of MetaboliteComponentSourceComments
Streptomyces sp. (ncbitaxon:1931) - PubMed (9711243) Strain: KY11783
Salinispora tropica CNB-440 (ncbitaxon:369723) - PubMed (21815669)
Salinispora arenicola CNS-205 (ncbitaxon:391037) - PubMed (21815669)
Salinispora pacifica (ncbitaxon:351187) - PubMed (21815669)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor  An EC 2.7.10.* (protein-tyrosine kinase) inhibitor that specifically blocks the action of non-specific protein-tyrosine kinase (EC 2.7.10.2).
marine metabolite  Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor  An inhibitor of phosphatidylinositol 3-kinase, EC 2.7.1.137, a family of related enzymes capable of phosphorylating the 3 position hydroxy group of the inositol ring of a phosphatidylinositol.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
ChEBI Ontology
Outgoing Relation(s)
lymphostin (CHEBI:157684) has role bacterial metabolite (CHEBI:76969)
lymphostin (CHEBI:157684) has role EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor (CHEBI:50914)
lymphostin (CHEBI:157684) has role EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor (CHEBI:76617)
lymphostin (CHEBI:157684) has role immunosuppressive agent (CHEBI:35705)
lymphostin (CHEBI:157684) has role marine metabolite (CHEBI:76507)
lymphostin (CHEBI:157684) is a acetamides (CHEBI:22160)
lymphostin (CHEBI:157684) is a alkaloid (CHEBI:22315)
lymphostin (CHEBI:157684) is a enol ether (CHEBI:47985)
lymphostin (CHEBI:157684) is a enone (CHEBI:51689)
lymphostin (CHEBI:157684) is a primary arylamine (CHEBI:50471)
lymphostin (CHEBI:157684) is a pyrroloquinoline (CHEBI:50918)
IUPAC Name 
N-{8-amino-4-[(2E)-3-methoxyprop-2-enoyl]pyrrolo[4,3,2-de]quinolin-6-yl}acetamide
Synonyms  Source
LK6-ASUBMITTER
LK 6AKNApSAcK
Manual XrefsDatabases
C00016344KNApSAcK
Registry NumbersSources
CAS:191474-39-2KNApSAcK
Citations