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 Summenformel: C₂₁H₃₉NO₆ Molekulargewicht: 401.54 EG-Nummer: 636-862-5

QUALITÄT & REINHEIT Moligand™, ≥98%

Synonyms

6-EICOSENOIC ACID, 2-AMINO-3,4-DIHYDROXY-2-(HYDROXYMETHYL)-14-OXO-, (2S,3R,4R,6E)|VRP|(2S,3R,4R,E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid|(E,2S,3R,4R)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid|Myriocin from Mycelia sterilia|Myriocin,mycella sterilia|MYRIOCIN [MI]|KASUGAMYCIN [HSDB]|ISP-1|Thermozymocidin;(2S,3R,4R,6E)-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic acid|(2S,3R,4R,6E)-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic acid|Myriocin, Mycelia sterilia - CAS 35891-70-4|thermozymocidin|ISP-I|6-Eicosenoic acid, 2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-, (2S-(2R*,3S*,4S*,6E))-|antibiotic ISP-I|N-(p-Aminobenzoyl)-L(+)-glutamic Acid|Myriocin|(+)-Myriocin|(2S,3R,4R,6E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid|(2S,3R,4R,6E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid'|Myriocin; ISP-1

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

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.

Spezifikationen

Synonyme

6-EICOSENOIC ACID, 2-AMINO-3,4-DIHYDROXY-2-(HYDROXYMETHYL)-14-OXO-, (2S,3R,4R,6E) | VRP | (2S,3R,4R,E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid | (E,2S,3R,4R)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid | Myriocin from Mycelia sterilia | Myriocin,mycella sterilia | MYRIOCIN [MI] | KASUGAMYCIN [HS Show more

Spezifikationen & Reinheit

Moligand™, ≥98%

Biochemische und physiologische Mechanismen

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.

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Note

Moligand™

Aktionsart

INHIBITOR

Mechanismus der Wirkung

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

Hinweis

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.

Reinheit

≥98%

Namen und Kennungen

Pubchem Sid

504764181

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504764181

Kanonisches Lächeln

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

Isomere SMILES

CCCCCCC(=O)CCCCCC/C=C/C[C@H]([C@@H]([C@@](CO)(C(=O)O)N)O)O

WGK Deutschland

3

RTECS

JX3890000

UN-Nummer

2811

Molekulargewicht

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
    • Klasse Fatty Acyls
      • Subclass Fatty acids and conjugates

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Klasse: 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
• Beschreibung: 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

Zugehörige Ziele (menschlich)

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

Zugehörige Ziele (nicht menschlich)

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)

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

Aspergillus niger (16508 Activities)

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

Bacillus subtilis (32866 Activities)

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

Bacillus cereus (7522 Activities)

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

Fusarium oxysporum (3998 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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Hepatitis C virus (23859 Activities)

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Botrytis cinerea (4183 Activities)

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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)

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Colletotrichum gloeosporioides (560 Activities)

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

Discover Target: fba

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Wirkungsmechanismen

Chemische und physikalische Eigenschaften

• Löslichkeit: 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.
• Empfindlichkeit: light sensitive & Moisture sensitive
• Molekulargewicht: 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