| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H24O6 |
| Molecular Weight | 372.4117 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C\C(CC[C@@H](O)C(C)(C)O)=C/COC1=C2C=COC2=CC3=C1C=CC(=O)O3
InChI
InChIKey=IXZUPBUEKFXTSD-INMULRNOSA-N
InChI=1S/C21H24O6/c1-13(4-6-18(22)21(2,3)24)8-10-26-20-14-5-7-19(23)27-17(14)12-16-15(20)9-11-25-16/h5,7-9,11-12,18,22,24H,4,6,10H2,1-3H3/b13-8+/t18-/m1/s1
| Molecular Formula | C21H24O6 |
| Molecular Weight | 372.4117 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 1 |
| Optical Activity | UNSPECIFIED |
6',7'-Dihydroxybergamottin is a natural furanocoumarin found principally in grapefruit juice. Along with the chemically related compound bergamottin, it is believed to be responsible for a number of grapefruit–drug interactions, in which the consumption of the juice affects the metabolism of a variety of pharmaceutical drugs.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 59.0 µM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
Patents
Sample Use Guides
HepG2-GS-3A4 cells, transduced with both hamster glutamine synthetase (GS) gene and human CYP3A4 gene were used for activity evaluation. One-hundred-thousand cells were seeded onto 24-well culture plates and grown to confluence. When cells were nearly confluent, the medium was replaced by 0.3 ml of phosphate-buffered saline (PBS) containing nifedipine (at a concentration of 28.9 mm) as a substrate of CYP3A4 and bergamottin (at a concentration of 0–3.0 mkm) or DHB (at a concentration of 0–5.9 mkm) as an inhibitor of CYP3A4. Samples of 0.1 ml were collected from the solution sequentially at 1 h after incubation at 37°C with 5%CO2. The concentration of oxidised nifedipine in these solutions was measured by high-performance liquid chromatography (HPLC).
