(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

• ChemBase ID: 132825
• Molecular Formular: C33H48O6
• Molecular Mass: 540.73062
• Monoisotopic Mass: 540.34508926
• SMILES: 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
• Canonical SMILES: CC/C(=C/[C@@H](C/C=C/C(=C/[C@H](C(=O)[C@H]([C@@H]([C@H](C/C(=C/C(=O)O)/C)C)O)C)C)/C)C)/C=C/[C@@H]1OC(=O)C=C[C@@H]1C
• InChI: 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
• InChIKey: YACHGFWEQXFSBS-XYERBDPFSA-N

NAMES AND DATABASE IDS

Names

• 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-3,6-dihydro-2H-pyran-2-yl]-8-oxononadeca-2,10,12,16,18-pentaenoic acid
• IUPAC Traditional name: leptomycin B
• Synonyms: Leptomycin B solution from Streptomyces sp.

Database IDs

• CAS Number: 87081-35-4
• MDL Number: MFCD06795848
• PubChem SID: 24896330; 162227102
• PubChem CID: 6917907

CALCULATED PROPERTIES

• Acid pKa: 4.568904
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 6.5972743
• LogD (pH = 7.4): 4.82295
• Log P: 7.575405
• Molar Refractivity: 162.478 cm^3
• Polarizability: 61.297455 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Flash Point: 18 °C; 64.4 °F

Safety Information

• European Hazard Symbols: Flammable (F); Toxic (T)
• UN Number: 1230
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 16-36/37-45
• GHS Pictograms: GHS02; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H301-H311-H331-H370
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P311
• RID/ADR: UN 1230 3/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Quality Level: PREMIUM
• Shipped in: dry ice

DETAILS

Sigma Aldrich - L2913

Biochem/physiol Actions
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 the HIV-1 Rev protein and Rev-dependent export of mRNA. The addition of very small amounts to fibroblasts causes accumulation of MEK in the nucleus. Other proteins that are influenced by leptomycin B are actin, c-Abl, cyclin B1, MDM2/p53, IκB, MPF, and PKA. The suggested inhibition mechanism involves the direct binding of leptomycin B to CRM1, which blocks the binding of CRM1 to proteins containing the nuclear export signal, via the interaction with cysteine residue in CRM1 control conserved region.
General description
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, I?B, MPF, PKA and MEK.