Leptomycin B - ≥98% , CAS No.87081-35-4

CAS: 87081-35-4 Cat. No.: L102387 Fórmula: C₃₃H₄₈O₆ Peso molecular: 540.73 Número CE: 617-954-4

GRAU & PUREZA Moligand™, ≥98%

Synonyms

2,10,12,16,18-Nonadecapentaenoic acid, 19-[(2S,3S)-3,6-dihydro-3-methyl-6-oxo-2H-pyran-2-yl]-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-,(2E,5S,6R,7S,9R,10E,12E,15R,16Z,18E)-|2,10,12,16,18-Nonadecapentanoic acid, 19-(3,6-dihydro-3-methyl-6-oxo-2H-pyran-2-yl)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-|Benzene, 1,1'-oxybis*4-methyl-|LMB|ATS 1287B|antibiotic ATS 1287B|Antibiotic PD 114720|Mantuamycin|Leptomycin B|(2E,5S,6R,7S,9R,10E,12E,15R,16Z,18E)-19-((2S,3S)-3,6-DIHYDRO-3-METHYL-6-OXO-2H-PYRAN-2-YL)-17-ETHYL-6-HYDROXY-3,5,7,9,11,15-HEXAMETHYL-8-OXO-2,10,12,16,18-NONADECAPENTAENOIC ACID|delta-chlorovaleric acid chloride|leptomycin|Leptomycin B, Streptomyces sp. ATS1287|(2E,5S,6R,7S,9R,10E,12E,15R,16Z,18E)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-19-[(2S,3S)-3-methyl-6-oxo-2,3-dihydropyran-2-yl]-8-oxo-nonadeca-2,10,12,16,18-pentaenoic acid|Antibiotic CI 940|Leptomycin B, Free Acid|PD 114720|PD-114720|LEPTOMYCIN B [MI]|(2E,10E,12E,16E,18E)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-19-(3-methyl-6-oxo-2,3-dihydropyran-2-yl)-8-oxo-nonadeca-2,10,12,16,18-pentaenoic acid|Elactocin|KOS-1688|CL 1957A|(2E,5S,6R,7S,9R,10E,12E,15R,16Z,18E)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-19-[(2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-8-oxononadeca-2,10,12,16,18-pentaenoic acid|(2E,5S,6R,7S,9R,10E,12E,15R,16Z,18E)-19-[(2S,3S)-3,6-Dihydro-3-methyl-6-oxo-2H-pyran-2-yl]-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-2,10,12,16,18-nonadecapentaenoic acid|CI 940|(2E,5S,6R,7S,9R,10E,12E,15R,16Z,18E)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-19-((2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-8-oxononadeca-2,10,12,16,18-pentaenoic acid|CL-1957A|Antibiotic CL 1957A|CI-940|4-hydroxy-benzenesulphonamide

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Visão geral

Leptomycin B is an anti-fungal antibiotic, anti-tumor cytotoxin that inhibits CRM1-dependent, NES-dependent nucleo-cytoplasmic translocation (nuclear export inhibitor). NES containing proteins include HIV-1 REV; actin, c-Abl, cyclin B1, MDM2/p53, IB, MPF, PKA and MEK.
Leptomycin B is a potent and specific nuclear export inhibitor. Leptomycin B alkylates and inhibits CRM1 (chromosomal region maintenance)/exportin 1, a protein required for nuclear export of proteins containing a nuclear export sequence (NES). In addition to antifungal and antibacterial activities, Leptomycin B blocks the cell cycle and is a potent anti-tumor agent. At low nM concentrations, Leptomycin B blocks the nuclear export of many proteins including HIV-1 Rev, MAPK/ERK, and NF-κB/IκB, and it stabilizes the expression of p53. Leptomycin B also inhibits the export and translation of many RNAs, including COX-2 and c-Fos mRNAs, by inhibiting export of ribonucleoproteins.

Especificações

Sinónimos

2,10,12,16,18-Nonadecapentaenoic acid, 19-[(2S,3S)-3,6-dihydro-3-methyl-6-oxo-2H-pyran-2-yl]-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-,(2E,5S,6R,7S,9R,10E,12E,15R,16Z,18E)- | 2,10,12,16,18-Nonadecapentanoic acid, 19-(3,6-dihydro-3-methyl-6-oxo-2H-pyran-2-yl)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo- | Benzene, 1,1'-oxybi Show more

Especificações e pureza

Moligand™, ≥98%

Mecanismos bioquímicos e fisiológicos

Leptomycin B is an unsaturated, branched-chain fatty acid, and is an important tool in the study of nuclear export. It is a specific inhibitor of proteins containing nuclear export signal. It inhibits nucleo-cytoplasmic translocation of molecules such as

Condições de armazenamento de armazenamento

Protected from light,Store at -20°C,Argon charged

Enviado em

Ice chest + Ice pads

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Grau

Moligand™

Tipo de ação

INHIBITOR

Nota

Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 6 months. 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. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureza

≥98%

Product Line

L102387-1mg

Nomes e identificadores

Pubchem Sid

528772130

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/528772130

Sorrisos canónicos

CCC(=CC(C)CC=CC(=CC(C)C(=O)C(C)C(C(C)CC(=CC(=O)O)C)O)C)C=CC1C(C=CC(=O)O1)C

IUPAC Name

(2E,5S,6R,7S,9R,10E,12E,15R,16Z,18E)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-19-[(2S,3S)-3-methyl-6-oxo-2,3-dihydropyran-2-yl]-8-oxononadeca-2,10,12,16,18-pentaenoic acid

InChIKey

YACHGFWEQXFSBS-XYERBDPFSA-N

INCHI

1S/C33H48O6/c1-9-28(14-15-29-24(5)13-16-31(36)39-29)19-22(3)12-10-11-21(2)17-25(6)32(37)27(8)33(38)26(7)18-23(4)20-30(34)35/h10-11,13-17,19-20,22,24-27,29,33,38H,9,12,18H2,1-8H3,(H,34,35)/b11-10+,15-14+,21-17+,23-20+,28-19-/t22-,24+,25-,26+,27-,29+,33-/m1/s1

SMILES isoméricas

CC/C(=C/[C@H](C)C/C=C/C(=C/[C@@H](C)C(=O)[C@@H](C)[C@@H]([C@@H](C)C/C(=C/C(=O)O)/C)O)/C)/C=C/[C@H]1[C@H](C=CC(=O)O1)C

WGK Alemanha

1

Peso molecular

540.73

Reaxy-Rn

28552826

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=28552826&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Fatty Acyls
• Subclass: Fatty acids and conjugates
• Intermediate Tree Nodes: Not available
• Direct Parent: Very long-chain fatty acids
• Alternative Parents: Diterpene lactones Diterpenoids Methyl-branched fatty acids Hydroxy fatty acids Heterocyclic fatty acids Dihydropyranones Unsaturated fatty acids Beta-hydroxy ketones Dicarboxylic acids and derivatives Enoate esters Secondary alcohols Lactones Oxacyclic compounds Carboxylic acids Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Very long-chain fatty acid - Diterpene lactone - Diterpenoid - Branched fatty acid - Dihydropyranone - Methyl-branched fatty acid - Heterocyclic fatty acid - Hydroxy fatty acid - Beta-hydroxy ketone - Dicarboxylic acid or derivatives - Unsaturated fatty acid - Pyran - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Carboxylic acid ester - Secondary alcohol - Lactone - Ketone - Organoheterocyclic compound - Oxacycle - Carboxylic acid - Carboxylic acid derivative - Hydrocarbon derivative - Alcohol - Carbonyl group - Organooxygen compound - Organic oxygen compound - Organic oxide - Aliphatic heteromonocyclic compound
• Descrição: This compound belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
• External Descriptors: leptomycin

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

Alvos associados (humanos)

XPO1 Tclin Exportin-1 (2 Activities)

Discover Target: XPO1

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

PC-3 (62116 Activities)

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

Alvos associados (não humanos)

Influenza A virus (11224 Activities)

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

COS-7 (515 Activities)

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MDCK (10148 Activities)

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

Mecanismos de ação

Propriedades químicas e físicas

• Solubilidade: Soluble in ethanol or methanol. Ethanol is recommended. Unstable in DMSO
• Sensibilidade: Moisture sensitive,Light sensitive
• Ponto de inflamação (°F): 64.4 °F
• Ponto de inflamação (°C): 18 °C
• Peso molecular: 540.700 g/mol
• XLogP3: 7.900
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 15
• Exact Mass: 540.345 Da
• Monoisotopic Mass: 540.345 Da
• Topological Polar Surface Area: 101.000 Ų
• Heavy Atom Count: 39
• Formal Charge: 0
• Complexity: 1020.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 7
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 5
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 5
• Covalently-Bonded Unit Count: 1