6-hydroxy-14-methoxy-10-oxo-12-pentanoyl-4-pentyl-2,9-dioxatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaene-5-carboxylic acid

• ChemBase ID: 179841
• Molecular Formular: C25H28O8
• Molecular Mass: 456.48502
• Monoisotopic Mass: 456.17841786
• SMILES: c12C(=O)Oc3c(Oc1cc(cc2C(=O)CCCC)OC)c(c(c(c3)O)C(=O)O)CCCCC
• Canonical SMILES: CCCCCc1c2Oc3cc(OC)cc(c3C(=O)Oc2cc(c1C(=O)O)O)C(=O)CCCC
• InChI: InChI=1S/C25H28O8/c1-4-6-8-9-15-21(24(28)29)18(27)13-20-23(15)32-19-12-14(31-3)11-16(17(26)10-7-5-2)22(19)25(30)33-20/h11-13,27H,4-10H2,1-3H3,(H,28,29)
• InChIKey: JHEWMLHQNRHTQX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-hydroxy-14-methoxy-10-oxo-12-pentanoyl-4-pentyl-2,9-dioxatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene-5-carboxylic acid
• IUPAC Traditional name: 6-hydroxy-14-methoxy-10-oxo-12-pentanoyl-4-pentyl-2,9-dioxatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene-5-carboxylic acid
• Synonyms: Usnetic acid; Lobaric acid

Database IDs

• CAS Number: 522-53-2
• PubChem SID: 164235751
• PubChem CID: 73157

CALCULATED PROPERTIES

• Acid pKa: 2.5666668
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 3.4113483
• LogD (pH = 7.4): 2.738666
• Log P: 6.2470856
• Molar Refractivity: 121.4209 cm^3
• Polarizability: 46.39167 Å^3
• Polar Surface Area: 119.36 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Leukotriene antagonist

Product Information

• Biological Source: Constit. of Anzia spp.
• Application(s): Antifungal

REFERENCES

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