5-hydroxy-3-(4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

• ChemBase ID: 156021
• Molecular Formular: C22H22O10
• Molecular Mass: 446.40408
• Monoisotopic Mass: 446.1212969
• SMILES: COc1ccc(cc1)c1coc2cc(cc(c2c1=O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)occ(c3=O)c2ccc(cc2)OC)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C22H22O10/c1-29-11-4-2-10(3-5-11)13-9-30-15-7-12(6-14(24)17(15)18(13)25)31-22-21(28)20(27)19(26)16(8-23)32-22/h2-7,9,16,19-24,26-28H,8H2,1H3/t16-,19-,20+,21-,22-/m1/s1
• InChIKey: LFEUICHQZGNOHD-RECXWPGBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-hydroxy-3-(4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
• IUPAC Traditional name: biochanin A-β-D-glucoside
• Synonyms: Biochanin A 7-O-β-D-glucopyranoside; Sissostrin; Sissotrin

Database IDs

• CAS Number: 5928-26-7
• MDL Number: MFCD00075975
• Beilstein Number: 1302648
• PubChem SID: 162250159; 24888358
• PubChem CID: 5280781

CALCULATED PROPERTIES

• Acid pKa: 7.282051
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): 0.94764197
• LogD (pH = 7.4): 0.5953233
• Log P: 0.9546983
• Molar Refractivity: 108.3096 cm^3
• Polarizability: 42.729126 Å^3
• Polar Surface Area: 155.14 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

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

Product Information

• Purity: ~95% (TLC)
• Empirical Formula (Hill Notation): C22H22O10
• Classification: Genuine Natural Compounds

DETAILS

Sigma Aldrich - 85447

General description
Flavonoid glycoside from Sophora japonica (Japanese pagoda tree), Cicer arietinum (chickpea), and other plant sources.2
Biochem/physiol Actions
Sissotrin in the leaf exudate of chickpea inactivates nucleopolyhedroviruses (such as baculovirus) which can be used as biological pesticides.1.