5,7-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one

• ChemBase ID: 174888
• Molecular Formular: C21H20O12
• Molecular Mass: 464.3763
• Monoisotopic Mass: 464.09547608
• SMILES: c1(cc(c2c(c1)oc(c(c2=O)OC1C(C(C(C(O1)C)O)O)O)c1cc(c(c(c1)O)O)O)O)O
• Canonical SMILES: Oc1cc(O)c2c(c1)oc(c(c2=O)OC1OC(C)C(C(C1O)O)O)c1cc(O)c(c(c1)O)O
• InChI: InChI=1S/C21H20O12/c1-6-14(26)17(29)18(30)21(31-6)33-20-16(28)13-9(23)4-8(22)5-12(13)32-19(20)7-2-10(24)15(27)11(25)3-7/h2-6,14,17-18,21-27,29-30H,1H3
• InChIKey: DCYOADKBABEMIQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
• IUPAC Traditional name: myricitrin
• Synonyms: 3-[(6-Deoxy-α-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one; Myricitrin; 3,3',4',5,5',7-Hexahydroxyflavone 3-Rhamnoside; Myricetin 3-O-α-L-Rhamnopyranoside; Myricetin 3-O-α-L-Rhamnoside; Myricetin 3-O-α-Rhamnopyranoside; Myricitroside; NSC 19803; Myricetin 3-Rhamnoside

Database IDs

• CAS Number: 17912-87-7
• PubChem SID: 164230798
• PubChem CID: 5352000

CALCULATED PROPERTIES

• Acid pKa: 6.4280925
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): 0.5503232
• LogD (pH = 7.4): -0.46496832
• Log P: 0.5985094
• Molar Refractivity: 109.7127 cm^3
• Polarizability: 42.182587 Å^3
• Polar Surface Area: 206.6 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M884110

It was isolated from the leaves of Myrtus communis; shows antimutagenic activity. Myricitrin was a very potent radical scavenger with an IC50 value of 1.4 .mu.g/mL. Moreover, this compound induced an inhibitory activity against nifuroxazide, aflatoxine B1

REFERENCES

• Edenharder, R., et al.: Mutation Res., 540, 1 (2003)
• Hayder, N., et al.: Pharmazie, 58, 523 (2003)
• Azam, S., et al.: Toxicology, 18, 555 (2003)
• Montoro, P., et al.: Food Chem., 92, 349 (2003)