Basic information
- CAS
87081-35-4- Standard SMILES
CCC(=C/[C@H](C)C/C=C/C(C)=C/[C@@H](C)C(=O)[C@@H](C)[C@H](O)[C@@H](C)C/C(C)=C/C(=O)O)/C=C/[C@@H]1OC(=O)C=C[C@@H]1C- InChIKey
YACHGFWEQXFSBS-XYERBDPFSA-N- Molecular formula
- C33H48O6
- Average molar mass
- 540.7 g/mol
- Monoisotopic mass
- 540.34508925
Overview
Leptomycin B is a leptomycin having a (2E,10E,12E,16Z,18E)-double bond configuration as well as an ethyl substituent at position 17. It has a role as an antifungal agent and a bacterial metabolite. It is a hydroxy polyunsaturated fatty acid and a leptomycin. It is functionally related to a tetracosanoic acid.
Names & identifiers
- Preferred name
- Leptomycin B
- IUPAC
- (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
- English name
- Leptomycin B
- Molecular formula
- C33H48O6
- Molecular weight
- 540.73
Names & synonyms
Leptomycin BElactocin87081-35-4Antibiotic CL 1957ACI-940Y031I2N1EOCHEBI:52646CL-1957ANSC-364372PD-114720(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)-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
Show more names
Lepomycin BLeprimycin Bantibioticci940antibioticcl1957aLeptomycin B solutioLeptomycin B (CI 940Leptomycin B (0.2mg/ml)LeptoMycin B 1% solutonInSolution? Leptomycin B,
2,10,12,16,18-Nonadecapentaenoic 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-DTXSID9036698RefChem:152842PD-114,720DTXCID7016698MantuamycinAntibiotic CI 940PD 114720
Properties
Computed structural properties
- XLogP
- 7.9
- Topological polar surface area
- 101 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 15
- Heavy atoms
- 39
- Formal charge
- 0
- Complexity
- 1,020
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
Physicochemical properties
- Melting point
- 41 · 41-44°, with prior softening (Hokanson)
- alpha
- -24.5 ° · D -24.5° (c = 0.70 in MeOH); D23 -157 ° (c = 0.7% in chloroform)
- Boiling point
- 725.8 · 725.8±60.0 °C(Predicted)
- Density
- 1.072 g/mL · 1.072 g/mL
- Flash point
- 13 °C · 13 °C
- storage temp.
- 20 °C · −20°C
- solubility
- Supplied in solution in ethanol (1 mg/ml). Further dilutions may be made with either ethanol or DMSO.
- form
- liquid
- pka
- 5.1 · 5.10±0.33(Predicted)
- color
- White to off-white
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions or dilutions in DMSO are not stable. Solutions should be made fresh and used within one working day.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P308+P316, P316, P321, P330, P361+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesFlam. Liq. 2 (100%)
Safety data
- wgk
- 3
- ridadr
- UN 1230 3/PG 2
- hs_code
- 29419090
- risk_code
- 23/25-36/38-39/23/24/25-23/24/25-11
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS06,GHS08
- hazard_code
- F,T
- safety_code
- 7-16-24-33-45-36/37
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- Hazard statements
- H225-H301+H311+H331-H370
- Hazard Classifications
- Eye Irrit. 2Flam. Liq. 2
- Precautionary statements
- P210-P280-P301+P310+P330-P302+P352+P312-P304+P340+P311
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms.
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Applications
DescriptionLeptomycin B (87081-35-4) is an inhibitor of nuclear export of proteins. Acts via covalent binding to and inhibiting CRM1/exportin-1.1 Inhibits the nuclear export of the HIV regulatory protein Rev.2 Leptomycin B stabilizes p53 by blocking its nuclear export.3
UsesBiological tool for studying nuclear localization and protein trafficking in eukaryotic cells.
UsesLeptomycin B is the dominant and most studied member of the leptomycin class, isolated from selected Streptomyces strains. Leptomycin B is a nanomolar active and specific nuclear export inhibitor. Its target is CRM1/exportin1, a protein in the nuclear export sequence (NES). Proteins affected include c-Abl, cyclin B1, HIV-1 Rev, IκB, MPF, MAP/ERK, MDM2/p53, NF-κB/IκB7 and PKA. Leptomycin B inhibits export of many RNAs, e.g. COX-2 and c-FOS mRNA. Leptomycin B also shows antifungal and antibacterial and potent antitumour activities.
UsesPotent, specific inhibitor of nuclear export signal (NES)-dependent protein export from the nucleus
General DescriptionLeptomycin 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.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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