4-{[(2E)-6,7-dihydroxy-3,7-dimethyloct-2-en-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one

• ChemBase ID: 154334
• Molecular Formular: C21H24O6
• Molecular Mass: 372.41166
• Monoisotopic Mass: 372.15728849
• SMILES: C/C(=C\COc1c2ccc(=O)oc2cc2c1cco2)/CCC(C(C)(C)O)O
• Canonical SMILES: C/C(=C\COc1c2ccoc2cc2c1ccc(=O)o2)/CCC(C(O)(C)C)O
• InChI: 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
• InChIKey: IXZUPBUEKFXTSD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(2E)-6,7-dihydroxy-3,7-dimethyloct-2-en-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one; 4-[(6,7-dihydroxy-3,7-dimethyloct-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one
• IUPAC Traditional name: 4-{[(2E)-6,7-dihydroxy-3,7-dimethyloct-2-en-1-yl]oxy}furo[3,2-g]chromen-7-one; 4-[(6,7-dihydroxy-3,7-dimethyloct-2-en-1-yl)oxy]furo[3,2-g]chromen-7-one
• Synonyms: 4-[[(2E)-6,7-Dihydroxy-3,7-dimethyl-2-octen-1-yl]oxy]-7H-furo[3,2-g][1]benzopyran-7-one; 6',7'-Dihydroxy Bergamottin; 6′,-7′-Dihydroxybergamottin

Database IDs

• CAS Number: 145414-76-2
• MDL Number: MFCD01310683
• PubChem SID: 162248473
• PubChem CID: 6440498

CALCULATED PROPERTIES

• Acid pKa: 13.842452
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.6653333
• LogD (pH = 7.4): 2.665333
• Log P: 2.6653333
• Molar Refractivity: 102.1213 cm^3
• Polarizability: 40.168457 Å^3
• Polar Surface Area: 89.13 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: white to off-white

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Empirical Formula (Hill Notation): C21H24O6

DETAILS

Sigma Aldrich - UC441

Biochem/physiol Actions
CYP3A4 inhibitor.

Toronto Research Chemicals - D452230

A minor metabolite of Bergamottin (B318400). Metabolization of Bergamottin by cytochromes P 450 2B6 and 3A5.

REFERENCES

• Lin, H., et al.: J. Pharmacol. Exp. Ther., 301, 160 (2002)
• Hesselink, D., et al.: Clin. Pharmacol. Ther., 74, 245 (2002)
• Evans, D., et al.: Chem. Res. Toxicol., 17, 3 (2002)
• Friesner, R., et al.: J. Med. Chem., 47, 1739 (2002)
• Bumpus, N., et al.: Drug