8,8-dimethyl-2-(propan-2-yl)-3,4,5,6,7,8-hexahydrophenanthrene-3,4-dione

• ChemBase ID: 174631
• Molecular Formular: C19H22O2
• Molecular Mass: 282.37678
• Monoisotopic Mass: 282.16197994
• SMILES: C1CC(c2c(C1)c1c(cc2)C=C(C(=O)C1=O)C(C)C)(C)C
• Canonical SMILES: CC(C1=Cc2ccc3c(c2C(=O)C1=O)CCCC3(C)C)C
• InChI: InChI=1S/C19H22O2/c1-11(2)14-10-12-7-8-15-13(6-5-9-19(15,3)4)16(12)18(21)17(14)20/h7-8,10-11H,5-6,9H2,1-4H3
• InChIKey: FEFAIBOZOKSLJR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8,8-dimethyl-2-(propan-2-yl)-3,4,5,6,7,8-hexahydrophenanthrene-3,4-dione
• IUPAC Traditional name: miltirone
• Synonyms: 5,6,7,8-Tetrahydro-8,8-dimethyl-2-(1-methylethyl)-3,4-phenanthrenedione; 5,6,7,8-Tetrahydro-2-isopropyl-8,8-dimethyl-3,4-phenanthrenedione; Miltiron; NSC 639662; Rosmariquinone; Miltirone

Database IDs

• CAS Number: 27210-57-7
• PubChem SID: 164230541
• PubChem CID: 160142

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.372758
• LogD (pH = 7.4): 5.372758
• Log P: 5.372758
• Molar Refractivity: 86.1776 cm^3
• Polarizability: 32.613434 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M344500

An active component in Salvia miltiorrhiza that has been shown to inhibit the increase in the abundance of the mRNA for the α4 subunit of the GABAA receptor induced by ethanol withdrawal in cultured hippocampal neurons. A potential phytotherapeutic agent

REFERENCES

• Mostallino, M. et al.: Eur. J. Pharmacol., 494, 83 (2004)
• Abenavoli, L. et al.: Rec. Prog. Med. Plants, 29, 19 (2004)
• Colombo, G. et al.: Alcohol. Clin. Exp. Res., 30, 754 (2004)