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:
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.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
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).
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Applications:
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.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
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
(2S,3R,4R,6E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic acidChEBI
(2S,3R,4R)-(E)-2-amino-3,4-dihydroxy-2-hydroxymethyl-14-oxoeicos-6-enoic acidChEBI
antibiotic ISP-1ChEBI
antibiotic ISP-IChEBI
ISP-1KEGG COMPOUND
ISP-IChEBI
Manual XrefsDatabases
C00016936KNApSAcK
C19914KEGG COMPOUND
LMFA01060203LIPID MAPS
MyriocinWikipedia
VRPPDBeChem
Registry NumbersSources
Reaxys:5113331Reaxys
CAS:35891-70-4ChemIDplus
Citations