Leptomycin B

Names

[ Name ]:
Leptomycin B

[Synonym ]:
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-nonadecapentaenoicacid
2,10,12,16,18-nonadecapentaenoic acid
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,16E,18E)-
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)-
7,9,11,15-hexamethyl-8-oxo--yl)-17-ethyl-6-hydroxy-5
(2E,5S,6R,7S,9R,10E,12E,15R,16E,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-oxo-2,10,12,16,18-nonadecapentaenoic acid
antibioticci940
(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-oxo-2,10,12,16,18-nonadecapentaenoic acid
antibioticcl1957a
LEPTOMYCIN B FROM STREPTOMYCES SP
Leptomycin B

Biological Activity

[Description]:

Leptomycin B (CI 940; LMB) is a potent inhibitor of the nuclear export of proteins. Leptomycin B inactivates CRM1/exportin 1 by covalent modification at a cysteine residue. Leptomycin B is a potent antifungal antibiotic blocking the eukaryotic cell cycle[1].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

Signaling Pathways >> Membrane Transporter/Ion Channel >> CRM1

[Target]

CRM1/exportin 1[1]

[References]

[1]. Kudo N, et al. Leptomycin B inactivates CRM1/exportin 1 by covalent modification at a cysteine residue in the central conserved region. Proc Natl Acad Sci U S A. 1999 Aug 3;96(16):9112-7.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
725.8±60.0 °C at 760 mmHg

[ Melting Point ]:
41-44ºC

[ Molecular Formula ]:
C₃₃H₄₈O₆

[ Molecular Weight ]:
540.73

[ Flash Point ]:
224.8±26.4 °C

[ Exact Mass ]:
540.345093

[ PSA ]:
100.90000

[ LogP ]:
6.66

[ Vapour Pressure ]:
0.0±5.3 mmHg at 25°C

[ Index of Refraction ]:
1.542

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RA5390000

CHEMICAL NAME :: 2,10,12,16,18-Nonadecapentanoic acid, 19-(3,6-dihydro-3-methyl-6-oxo-2H-pyran-2-yl)-17-ethy l- 6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-

CAS REGISTRY NUMBER :: 87081-35-4

LAST UPDATED :: 199412

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C33-H48-O6

MOLECULAR WEIGHT :: 540.81

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3100 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Rodent - mouse Leukocyte

DOSE/DURATION :: 1 umol/L

REFERENCE :: PAACA3 Proceedings of the American Association for Cancer Research. (Waverly Press, 428 E. Preston St., Baltimore, MD 21202) V.1- 1954- Volume(issue)/page/year: 26,253,1985

Safety Information

[ Symbol ]:

GHS02, GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H301-H311-H331-H370

[ Precautionary Statements ]:
P210-P260-P280-P301 + P310-P311

[ Hazard Codes ]:
T: Toxic;F: Flammable;

[ Risk Phrases ]:
R23/25

[ Safety Phrases ]:
7-16-24-33-45

[ RIDADR ]:
UN 1230 3

[ WGK Germany ]:
3

[ HS Code ]:
2916190090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2916190090

[ Summary ]:
2916190090 unsaturated acyclic monocarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives。supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward)。VAT:17.0%。tax rebate rate:9.0%。MFN tariff:6.5%。general tariff:30.0%

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