CHEBI:144441 - triacsin C

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ChEBI Name triacsin C
ChEBI ID CHEBI:144441
Definition A nitroso compound that is N-undecylnitrous hydrazide carrying double bonds at positions 1,2,4, and 7. It is a long-chain fatty acyl CoA synthetase inhibitor and interferes with lipid metabolism by inhibiting the de novo synthesis of glycerolipids and cholesterol esters.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Sandra Orchard
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Formula C11H17N3O
Net Charge 0
Average Mass 207.277
Monoisotopic Mass 207.13716
InChI InChI=1S/C11H17N3O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15/h4-5,7-11H,2-3,6H2,1H3,(H,13,15)/b5-4+,8-7+,10-9+,12-11+
InChIKey NKTGCVUIESDXPU-YLEPRARLSA-N
SMILES C(/C=C/C=C/C/C=C/CCC)=N\NN=O
Metabolite of Species Details
Streptomyces aureofaciens (NCBI:txid1894) Found in cell suspension culture (BTO:0000221). of strain 1228 See: PubMed
Roles Classification
Biological Role(s): EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor
An EC 6.2.1.* (acid-thiol ligase) inhibitor that interferes with the action of a long-chain-fatty-acidCoA ligase (EC 6.2.1.3).
apoptosis inhibitor
Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
EC 3.1.1.64 (retinoid isomerohydrolase) inhibitor
An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of retinoid isomerohydrolase (EC 3.1.1.64).
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
Application(s): vasodilator agent
A drug used to cause dilation of the blood vessels.
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
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ChEBI Ontology
Outgoing triacsin C (CHEBI:144441) has role antimalarial (CHEBI:38068)
triacsin C (CHEBI:144441) has role apoptosis inhibitor (CHEBI:68494)
triacsin C (CHEBI:144441) has role bacterial metabolite (CHEBI:76969)
triacsin C (CHEBI:144441) has role EC 3.1.1.64 (retinoid isomerohydrolase) inhibitor (CHEBI:144455)
triacsin C (CHEBI:144441) has role EC 6.2.1.3 (long-chain-fatty-acid—CoA ligase) inhibitor (CHEBI:83157)
triacsin C (CHEBI:144441) has role vasodilator agent (CHEBI:35620)
triacsin C (CHEBI:144441) is a hydrazone (CHEBI:38532)
triacsin C (CHEBI:144441) is a nitroso compound (CHEBI:35800)
triacsin C (CHEBI:144441) is a olefinic compound (CHEBI:78840)
IUPAC Name
N-[(1E,2E,4E,7E)-undeca-2,4,7-trien-1-ylidene]nitrous hydrazide
Synonyms Sources
(2E,4E,7E)-2,4,7-undecatrienal nitrosohydrazone ChEBI
(2E,4E,7E)-undecatrienal nitrosohydrazone ChEBI
2,4,7-undecatrienal nitrosohydrazone
Note: (2019-08-08) ambiguous - The name is used by several chemical suppliers.
 ChEBI
FR 900190 ChemIDplus
nitrosohydrazone-2E,4E,7E-undecatrienal ChEBI
WS 1228A ChemIDplus
WS-1228A ChEBI
Manual Xrefs Databases
CPD-14770 MetaCyc
LSM-43284 LINCS
Triacsin_C Wikipedia
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Registry Number Type Source
76896-80-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15249192 PubMed citation Europe PMC
17446697 PubMed citation Europe PMC
18653998 PubMed citation Europe PMC
1999415 PubMed citation Europe PMC
23565210 PubMed citation Europe PMC
26719343 PubMed citation Europe PMC
28918598 PubMed citation Europe PMC
3117118 PubMed citation Europe PMC
6804425 PubMed citation Europe PMC
6804426 PubMed citation Europe PMC
9182714 PubMed citation Europe PMC
Last Modified
09 August 2019