(3E,5S,8R,11E,13S,16R)-5,13-dihydroxy-8,16-dimethyl-1,9-dioxacyclohexadeca-3,11-diene-2,10-dione

• ChemBase ID: 177141
• Molecular Formular: C16H24O6
• Molecular Mass: 312.35816
• Monoisotopic Mass: 312.15728849
• SMILES: C1C[C@@H](/C=C/C(=O)O[C@@H](CC[C@@H](/C=C/C(=O)O[C@@H]1C)O)C)O
• Canonical SMILES: O[C@H]1CC[C@@H](C)OC(=O)/C=C/[C@H](CC[C@H](OC(=O)/C=C/1)C)O
• InChI: InChI=1S/C16H24O6/c1-11-3-5-13(17)8-10-16(20)22-12(2)4-6-14(18)7-9-15(19)21-11/h7-14,17-18H,3-6H2,1-2H3/b9-7+,10-8+/t11-,12-,13+,14+/m1/s1
• InChIKey: RBQNDQOKFICJGL-UTBFYLPBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3E,5S,8R,11E,13S,16R)-5,13-dihydroxy-8,16-dimethyl-1,9-dioxacyclohexadeca-3,11-diene-2,10-dione
• IUPAC Traditional name: (3E,5S,8R,11E,13S,16R)-5,13-dihydroxy-8,16-dimethyl-1,9-dioxacyclohexadeca-3,11-diene-2,10-dione
• Synonyms: (3E,5S,8R,11E,13S,16R)-5,13-Dihydroxy-8,16-dimethyl-1,9-dioxacyclohexadeca-3,11-diene-2,10-dione; (-)-5,13-Dihydroxy-8,16-dimethyl-1,9-dioxacyclohexadeca-3,11-diene-2,10-dione; Pyrenophorol; (-)-Pyrenophorol

Database IDs

• CAS Number: 22248-41-5
• PubChem SID: 164233051
• PubChem CID: 10935870

CALCULATED PROPERTIES

• Acid pKa: 14.527974
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.8003561
• LogD (pH = 7.4): 1.8003561
• Log P: 1.8003561
• Molar Refractivity: 82.2774 cm^3
• Polarizability: 31.817646 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P989610

The macrolide dilactone Pyrenophorol was originally isolated from Byssochlamys niveah and Stemphylium radicinum. Pyrenophorol was moderately active against the fungus Microbotryum violaceum. It is an anti-fungal antibiotic produced by the plant pathogenic

REFERENCES

• Christner, C., et al.: J. Antibiot., 51, 368 (1998)
• Holler, U., et al.: Mycol. Res., 104, 1354 (1998)
• Krohn, K., et al.: Nat. Prod. Lett., 15, 353 (1998)