CHEBI:157684 - lymphostin

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ChEBI Name lymphostin
ChEBI ID CHEBI:157684
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Martin Larralde
Supplier Information
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Formula C16H14N4O3
Net Charge 0
Average Mass 310.313
Monoisotopic Mass 310.10659
InChI InChI=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+
InChIKey HQPIKMNKCMXJQC-ONEGZZNKSA-N
SMILES CO\C=C\C(=O)C1=NC2=C3C(C=NC3=C(N)C=C2NC(C)=O)=C1
Metabolite of Species Details
Streptomyces sp. (NCBI:txid1931) of strain KY11783 See: PubMed
Salinispora pacifica (NCBI:txid351187) See: PubMed
Salinispora tropica CNB-440 (NCBI:txid369723) See: PubMed
Salinispora arenicola CNS-205 (NCBI:txid391037) See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 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).
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.
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.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
marine metabolite
Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
LK 6A KNApSAcK
LK6-A SUBMITTER
Manual Xref Database
C00016344 KNApSAcK
View more database links
Registry Number Type Source
191474-39-2 CAS Registry Number KNApSAcK
Citations Waiting for Citations Types Sources
12005041 PubMed citation SUBMITTER
21815669 PubMed citation SUBMITTER
27866908 PubMed citation Europe PMC
9711243 PubMed citation SUBMITTER
9711244 PubMed citation SUBMITTER
Last Modified
09 November 2020