CHEBI:582124 - myriocin

ChEBI IDCHEBI:582124
ChEBI Namemyriocin
Stars
DefinitionAn amino acid-based antibiotic derived from certain thermophilic fungi; acts as a potent inhibitor of serine palmitoyltransferase, the first step in sphingosine biosynthesis. Myriocin also possesses immunosuppressant activity.
Last Modified25 November 2021
DownloadsMolfile
FormulaC21H39NO6
Net Charge0
Average Mass401.544
Monoisotopic Mass401.27774
SMILESCCCCCCC(=O)CCCCCC/C=C/C[C@@H](O)[C@H](O)[C@@](N)(CO)C(=O)O
InChIInChI=1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28)/b12-9+/t18-,19+,21+/m1/s1
InChIKeyZZIKIHCNFWXKDY-GNTQXERDSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Isaria sinclairii (fungorum:254719) - PubMed (21456524) Entomopathogenic fungus
Myriococcum albomyces (fungorum:335011) - PubMed (21456524)
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
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.
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
EC 2.3.1.50 (serine C-palmitoyltransferase) inhibitor  An EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor that interferes with the action of serine palmitoyltransferase (EC 2.3.1.50).
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
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)
myriocin (CHEBI:582124) has role antifungal agent (CHEBI:35718)
myriocin (CHEBI:582124) has role antimicrobial agent (CHEBI:33281)
myriocin (CHEBI:582124) has role antineoplastic agent (CHEBI:35610)
myriocin (CHEBI:582124) has role apoptosis inducer (CHEBI:68495)
myriocin (CHEBI:582124) has role EC 2.3.1.50 (serine C-palmitoyltransferase) inhibitor (CHEBI:59647)
myriocin (CHEBI:582124) has role fungal metabolite (CHEBI:76946)
myriocin (CHEBI:582124) has role immunosuppressive agent (CHEBI:35705)
myriocin (CHEBI:582124) is a hydroxy monocarboxylic acid (CHEBI:35868)
myriocin (CHEBI:582124) is a non-proteinogenic α-amino acid (CHEBI:83925)
myriocin (CHEBI:582124) is a sphingoid (CHEBI:35785)
myriocin (CHEBI:582124) is a α-amino fatty acid (CHEBI:59755)
IUPAC Name 
(2S,3R,4R,6E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid
Synonyms  Source
thermozymocidinChemIDplus
antibiotic ISP-IChEBI
(2S,3R,4R,6E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic acidChEBI
ISP-1KEGG COMPOUND
(2S,3R,4R)-(E)-2-amino-3,4-dihydroxy-2-hydroxymethyl-14-oxoeicos-6-enoic acidChEBI
ISP-IChEBI
Manual XrefsDatabases
MyriocinWikipedia
LMFA01060203LIPID MAPS
C00016936KNApSAcK
C19914KEGG COMPOUND
VRPPDBeChem
Registry NumbersSources
Reaxys:5113331Reaxys
CAS:35891-70-4ChemIDplus
Citations