4,10-diacetyl-11,13-dihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.02,7]trideca-1(13),6,9,11-tetraene-3,5-dione

• ChemBase ID: 130106
• Molecular Formular: C18H16O7
• Molecular Mass: 344.31544
• Monoisotopic Mass: 344.08960285
• SMILES: Cc1c(c(c2c(c1O)C1(C(=CC(=O)C(C1=O)C(=O)C)O2)C)C(=O)C)O
• Canonical SMILES: CC(=O)C1C(=O)C=C2C(C1=O)(C)c1c(O)c(C)c(c(c1O2)C(=O)C)O
• InChI: InChI=1S/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,11,22-23H,1-4H3
• InChIKey: CUCUKLJLRRAKFN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,10-diacetyl-11,13-dihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0^2,^7]trideca-1(13),6,9,11-tetraene-3,5-dione
• IUPAC Traditional name: 7-hydroxy-(S)-usnate
• Synonyms: usneine; usninic acie; usniacin; Usnic acid

Database IDs

• CAS Number: 125-46-2
• PubChem SID: 162224391
• PubChem CID: 5646
• CHEMBL: 242022
• Chemspider ID: 5444
• Wikipedia Title: Usnic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.6442661
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 0.7202283
• LogD (pH = 7.4): 0.07327041
• Log P: 2.3895414
• Molar Refractivity: 88.5472 cm^3
• Polarizability: 32.931072 Å^3
• Polar Surface Area: 117.97 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 204 °C