Myriocin - Moligand™, ≥98% , Inhibitor of serine palmitoyltransferase long chain base subunit 1;Inhibitor of serine palmitoyltransferase long chain base subunit 2;Inhibitor of serine palmitoyltransferase long chain base subunit 3, CAS No.35891-70-4, Inhibitor of serine palmitoyltransferase long chain base subunit 1;Inhibitor of serine palmitoyltransferase long chain base subunit 2;Inhibitor of serine palmitoyltransferase long chain base subunit 3

CAS: 35891-70-4 Cat. No.: M102400 Peso molecular: 401.54 Número EC: 636-862-5

GRADE & PURITY Moligand™, ≥98%

Synonyms

6-EICOSENOIC ACID, 2-AMINO-3,4-DIHYDROXY-2-(HYDROXYMETHYL)-14-OXO-, (2S,3R,4R,6E) | SR-05000002333-3 | UNII-YRM4E8R9ST | VRP | YRM4E8R9ST | F85634 | NCGC00163597-04 | (2S,3R,4R,E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid | (E,2S,3R,

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

Myriocin is an amino fatty acid antibiotic derived from certain thermophylic fungi, in this case Mycelia sterilia. It is a potent immunosuppressant having 10- to 100-fold more activity than cyclosporin A. Myriocin is a potent inhibitor of serine palmitoyltransferase (Ki = 0.28 nM), the enzyme that catalyzes the first step of sphingolipid biosynthesis. It disrupts substratum adhesion of melanoma cells. It also suppresses cell proliferation in the murine cytotoxic T cell line CTLL-2 (IC50 = 15 nM) via apoptosis. Myriocin suppresses replication of the hepatitis C virus (HCV) in a murine model.
An inhibitor of sphingolipid biosynthesis with immunosuppressive properties.

Specifications

Sinónimos

6-EICOSENOIC ACID, 2-AMINO-3, 4-DIHYDROXY-2-(HYDROXYMETHYL)-14-OXO-, (2S, 3R, 4R, 6E) | SR-05000002333-3 | UNII-YRM4E8R9ST | VRP | YRM4E8R9ST | F85634 | NCGC00163597-04 | (2S, 3R, 4R, E)-2-amino-3, 4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid | (E, 2S, 3R,

Especificaciones y pureza

Moligand™, ≥98%

Mecanismos bioquímicos y fisiológicos

Fungal metabolite with potent immunosuppressant activity. Inhibits serine palmitoyltransferase at picomolar concentrations blocking synthesis of ceramide, a precursor of sphingomyelin and glycosphingolipids. Disrupts substratum adhesion of melanoma cells.

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Moligand™

Tipo de acción

INHIBITOR

Mecanismo de acción

Inhibitor of serine palmitoyltransferase long chain base subunit 1;Inhibitor of serine palmitoyltransferase long chain base subunit 2;Inhibitor of serine palmitoyltransferase long chain base subunit 3

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Toxic, refer to SDS for further information. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 504764181
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504764181
• Sonrisas canónicas: CCCCCCC(=O)CCCCCCC=CCC(C(C(CO)(C(=O)O)N)O)O
• IUPAC Name: (E,2S,3R,4R)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid
• InChIKey: ZZIKIHCNFWXKDY-GNTQXERDSA-N
• 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
• Isómeros SMILES: CCCCCCC(=O)CCCCCC/C=C/C[C@H]([C@@H]([C@@](CO)(C(=O)O)N)O)O
• WGK Alemania: 3
• RTECS: JX3890000
• Número ONU: 2811
• Peso molecular: 401.54
• Reaxy-Rn: 30186535
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=30186535&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Clase Fatty Acyls
      • Subclass Fatty acids and conjugates

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: Fatty Acyls
• Subclass: Fatty acids and conjugates
• Intermediate Tree Nodes: Not available
• Direct Parent: Long-chain fatty acids
• Alternative Parents: D-alpha-amino acids L-alpha-amino acids Amino fatty acids Beta hydroxy acids and derivatives Branched fatty acids Hydroxy fatty acids Keto fatty acids Unsaturated fatty acids 1,3-aminoalcohols Secondary alcohols Ketones Amino acids Carboxylic acids Monocarboxylic acids and derivatives Hydrocarbon derivatives Monoalkylamines Organic oxides Organopnictogen compounds Primary alcohols
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Long-chain fatty acid - Alpha-amino acid - Alpha-amino acid or derivatives - D-alpha-amino acid - L-alpha-amino acid - Amino fatty acid - Beta-hydroxy acid - Branched fatty acid - Hydroxy fatty acid - Keto fatty acid - Unsaturated fatty acid - Hydroxy acid - 1,3-aminoalcohol - Amino acid - Secondary alcohol - Amino acid or derivatives - Ketone - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Carboxylic acid - Primary aliphatic amine - Organic oxide - Primary amine - Carbonyl group - Alcohol - Hydrocarbon derivative - Organonitrogen compound - Amine - Organooxygen compound - Primary alcohol - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Aliphatic acyclic compound
• Descripción: This compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
• External Descriptors: non-proteinogenic alpha-amino acid - alpha-amino fatty acid - sphingoid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

SPTLC2 Tchem Serine palmitoyltransferase 2 (1 Activities)

Discover Target: SPTLC2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SPTLC3 Tbio Serine palmitoyltransferase 3 (0 Activities)

Discover Target: SPTLC3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SPTLC1 Tchem Serine palmitoyltransferase 1 (2 Activities)

Discover Target: SPTLC1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AKT1 Tchem Serine/threonine-protein kinase AKT (9192 Activities)

Discover Target: AKT1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SPTLC1 Tchem Serine palmitoyltransferase 1 (9 Activities)

Discover Target: SPTLC1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SPTLC2 Tchem Serine palmitoyltransferase 2 (14 Activities)

Discover Target: SPTLC2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PMP22 Tbio Peripheral myelin protein 22 (699 Activities)

Discover Target: PMP22

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Objetivos asociados (no humanos)

Fdft1 Squalene synthetase (34 Activities)

Discover Target: Fdft1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Galc Galactocerebrosidase (11 Activities)

Discover Target: Galc

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Escherichia coli (133304 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Aspergillus niger (16508 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Bacillus subtilis (32866 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Bacillus cereus (7522 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Fusarium oxysporum (3998 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mus musculus (284745 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rattus norvegicus (775804 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Hepatitis C virus (23859 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Botrytis cinerea (4183 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Akt1 RAC-alpha serine/threonine-protein kinase (147 Activities)

Discover Target: Akt1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Colletotrichum fragariae (147 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Colletotrichum gloeosporioides (560 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)

Discover Target: fba

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in DMSO (heat briefly in boiling water bath) (25 mg/ml), dilute base (50 mM NaOH) (~5 mg/ml), and methanol (2 mg/ml). Insoluble in water.
• Sensibilidad: light sensitive & Moisture sensitive
• Peso molecular: 401.500 g/mol
• XLogP3: -0.100
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 18
• Exact Mass: 401.278 Da
• Monoisotopic Mass: 401.278 Da
• Topological Polar Surface Area: 141.000 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 468.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

Referencias

1. Hui Lu, Wanqian Li, Malcolm Whiteway, Hongkang Wang, Shuo Zhu, Zhe Ji, Yanru Feng, Lan Yan, Ting Fang, Liping Li, Tingjunhong Ni, Xiaolong Zhang, Quanzhen Lv, Zichao Ding, Lijuan Qiu, Dazhi Zhang, Yuanying Jiang.  (2022)  A Small Molecule Inhibitor of Erg251 Makes Fluconazole Fungicidal by Inhibiting the Synthesis of the 14α-Methylsterols.  mBio,  14  (1):   [PMID:36475771] [10.1128/mbio.02639-22]

2. Xin Yang, Zejun Pei, Renjing Hu, Zhehao Zhang, Zaixiang Lou, Xin Sun.  (2021)  Study on the Inhibitory Activity and Possible Mechanism of Myriocin on Clinically Relevant Drug-Resistant Candida albicans and Its Biofilms.  BIOLOGICAL & PHARMACEUTICAL BULLETIN,  44  (3): (305-315).  [PMID:33441497] [10.1248/bpb.b20-00246]

3. Li Wanqian, Whiteway Malcolm, Hang Sijin, Yu Jinhua, Lu Hui, Jiang Yuanying.  (2025)  Impairing the interaction between Erg11 and cytochrome P450 reductase Ncp1 enhances azoles’ antifungal activities.  Nature Communications,  16  (1): (1-18).  [PMID:40707518] [10.1038/s41467-025-62131-z]