6-hydroxy-3,5,7,9,11,15,17-heptamethyl-19-(3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-8-oxononadeca-2,10,12,16,18-pentaenoic acid

• ChemBase ID: 154390
• Molecular Formular: C32H46O6
• Molecular Mass: 526.70404
• Monoisotopic Mass: 526.32943919
• SMILES: CC1C=CC(=O)OC1/C=C/C(=C/C(C)C/C=C/C(=C/C(C)C(=O)C(C)C(C(C)C/C(=C/C(=O)O)/C)O)/C)/C
• Canonical SMILES: C/C(=C\C(C(=O)C(C(C(C/C(=C/C(=O)O)/C)C)O)C)C)/C=C/CC(/C=C(/C=C/C1OC(=O)C=CC1C)\C)C
• InChI: InChI=1S/C32H46O6/c1-20(16-22(3)12-14-28-24(5)13-15-30(35)38-28)10-9-11-21(2)17-25(6)31(36)27(8)32(37)26(7)18-23(4)19-29(33)34/h9,11-17,19-20,24-28,32,37H,10,18H2,1-8H3,(H,33,34)
• InChIKey: QECBVZBMGUAZDL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-hydroxy-3,5,7,9,11,15,17-heptamethyl-19-(3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-8-oxononadeca-2,10,12,16,18-pentaenoic acid
• IUPAC Traditional name: 6-hydroxy-3,5,7,9,11,15,17-heptamethyl-19-(3-methyl-6-oxo-2,3-dihydropyran-2-yl)-8-oxononadeca-2,10,12,16,18-pentaenoic acid
• Synonyms: 19-(3,6-Dihydro-3-methyl-6-oxo-2H-pyran-2-yl)-3,5,7,9,11,15,17-heptamethyl-6-hydroxy-8-oxo-2,10,12,16,18-nonadecapentaenoic acid; Jildamycin; Leptomycin A; Leptomycin A 来源于链霉菌 属

Database IDs

• CAS Number: 87081-36-5
• MDL Number: MFCD01711669
• PubChem SID: 162248529
• PubChem CID: 5384875

CALCULATED PROPERTIES

• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false
• Acid pKa: 4.568904
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 6.1527057
• LogD (pH = 7.4): 4.3783813
• Log P: 7.1308365
• Molar Refractivity: 157.877 cm^3
• Polarizability: 59.455105 Å^3

PROPERTIES

Physical Property

• Apperance: methanol solution

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: 7-16-36/37-45
• RID/ADR: UN 1230 3/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ~95% (HPLC)
• Biological Source: from Streptomyces sp.
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C32H46O6

DETAILS

Sigma Aldrich - L6417

Biochem/physiol Actions
Leptomycins are antifungal antibiotics with unique unsaturated, branched-chain fatty acid structures.1, The physiochemical and biological properties of Leptomycins A and B are very similar.2, Both are considered to be specific inhibitors of nuclear export. The suggested inhibition mechanism involves the direct binding of leptomycins to CRM1 (Exportin-1), which is the main nuclear export protein. This blocks the binding of CRM1 to proteins containing a nuclear export signal (NES),3,4 and therefore prevents their export from the nucleus. Although more research on nuclear export inhibition has been performed using Leptomycin B, it has been shown that Leptomycin A has similar effects and can induce, for example, nuclear accumulation of wild-type ERK5.5Leptomycin A is also active against Schizosaccaromyces pombe and Mucor rouxianus.2