(1R,5S,6R,7S)-4-hydroxy-6-methyl-1,3,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)-5-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione

• ChemBase ID: 155764
• Molecular Formular: C35H52O4
• Molecular Mass: 536.78498
• Monoisotopic Mass: 536.38656014
• SMILES: CC(C)C(=O)[C@]12C(=C(C(=O)[C@](C1=O)(C[C@@H]([C@@]2(C)CCC=C(C)C)CC=C(C)C)CC=C(C)C)CC=C(C)C)O
• Canonical SMILES: CC(=CCC[C@]1(C)[C@@H](CC=C(C)C)C[C@]2(C(=O)[C@]1(C(=O)C(C)C)C(=C(C2=O)CC=C(C)C)O)CC=C(C)C)C
• InChI: InChI=1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,38H,12,16-17,19-21H2,1-11H3/t27-,33+,34+,35-/m0/s1
• InChIKey: IWBJJCOKGLUQIZ-HQKKAZOISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,5S,6R,7S)-4-hydroxy-6-methyl-1,3,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)-5-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione
• IUPAC Traditional name: hyperforine
• Synonyms: Hyperforin

Database IDs

• CAS Number: 11079-53-1
• MDL Number: MFCD01861497
• PubChem SID: 162249902
• PubChem CID: 441298

CALCULATED PROPERTIES

• Acid pKa: 6.315648
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 9.604594
• LogD (pH = 7.4): 8.549195
• Log P: 9.666359
• Molar Refractivity: 166.6825 cm^3
• Polarizability: 63.38986 Å^3
• Polar Surface Area: 71.44 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solution

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥85% (HPLC)
• Concentration: 0.25 mg/mL in methanol
• Empirical Formula (Hill Notation): C35H52O4

DETAILS

Sigma Aldrich - H5160

Biochem/physiol Actions
Active antidepressant component of St. John′s wort.