TABLE 1.

Estrogenic activities of odorants

The compound concentrations EC₅₀ evoking half-maximal estrogenic activity in transcription activation, the dissociation inhibition constants K_i calculated from the IC₅₀ values of the ES2 displacement curves (Fig. 1), and the corresponding K_i values calculated using the 6D-QSAR model are compared. For Polysantol and Javanol only the K_i values for the energetically most favorable conformation are reported. The IC₅₀ values for the remaining stereoisomers are as follows: 140 ± 173 μm Polysantol (S,S), 216 ± 122 μm Polysantol (S,R), 2.86 ± 4.45 mm Polysantol (R,R), 2.41 ± 2.64 mm Javanol (R,S), 176.7 ± 567 μm Javanol (S,S), and 40.73 ± 23.33 μm Javanol (S,R). The K_i values for the remaining stereoisomeric forms are as follows: 299 μm Polysantol (S,S), 83 μm Polysantol (S,R), 1 mm Polysantol (R,R), 931 μm Javanol (R,S), 68 μm Javanol (S,S), and 15 μm Javanol (S,R).

Compound	EC50 of ERactivation	Ki of ERcompetitive binding	Ki of ER predicted
Estradiol	0.16 ± 0.01 nm	1.6 ± 1 nm	2 nm
MC	86 ± 8 mm	76 ± 6 μm	21 μm
Polysantol (R,S)a	98 ± 23 mm	56 ± 5 μm	26 μm
Javanol (R,R)a	50 ± 4 mm	ca. 50 μm	5 μm
Androstenol	52 ± 3 mm	ca. 25 μm	10 μm

^a The indicated stereoisomers were used for predicting K_i values, whereas experiments were performed using mixtures of stereoisomers.