CHEBI:582124 - myriocin

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ChEBI Name myriocin
ChEBI ID CHEBI:582124
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H39NO6
Net Charge 0
Average Mass 401.53750
Monoisotopic Mass 401.278
InChI InChI=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
InChIKey ZZIKIHCNFWXKDY-GNTQXERDSA-N
SMILES CCCCCCC(=O)CCCCCC\C=C\C[C@@H](O)[C@H](O)[C@@](N)(CO)C(O)=O
Metabolite of Species Details
Isaria sinclairii (IF:254719) Entomopathogenic fungus See: PubMed
Myriococcum albomyces (IF:335011) See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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.
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 2.3.1.50 (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).
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
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.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing 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 α-amino fatty acid (CHEBI:59755)
myriocin (CHEBI:582124) is a non-proteinogenic α-amino acid (CHEBI:83925)
myriocin (CHEBI:582124) is a sphingoid (CHEBI:35785)
IUPAC Name
(2S,3R,4R,6E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid
Synonyms Sources
antibiotic ISP-I ChEBI
Thermozymocidin ChemIDplus
Database Link Database
Myriocin Wikipedia
View more database links
Registry Numbers Types Sources
35891-70-4 CAS Registry Number ChemIDplus
5113331 Beilstein Registry Number Beilstein
5113331 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15679316 PubMed citation ChEMBL
21456524 PubMed citation Europe PMC
23178537 PubMed citation Europe PMC
23659342 PubMed citation Europe PMC
23802886 PubMed citation Europe PMC
23957439 PubMed citation Europe PMC
24141140 PubMed citation Europe PMC
24395529 PubMed citation Europe PMC
24456332 PubMed citation Europe PMC
Last Modified
26 March 2015