7-hydroxy-3-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

• ChemBase ID: 130762
• Molecular Formular: C21H20O9
• Molecular Mass: 416.3781
• Monoisotopic Mass: 416.11073222
• SMILES: c1cc(ccc1c1coc2c(c1=O)ccc(c2[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)c1c(O)ccc2c1occ(c2=O)c1ccc(cc1)O
• InChI: InChI=1S/C21H20O9/c22-7-14-17(26)18(27)19(28)21(30-14)15-13(24)6-5-11-16(25)12(8-29-20(11)15)9-1-3-10(23)4-2-9/h1-6,8,14,17-19,21-24,26-28H,7H2/t14-,17-,18+,19-,21+/m1/s1
• InChIKey: HKEAFJYKMMKDOR-VPRICQMDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-hydroxy-3-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
• IUPAC Traditional name: puerarin
• Synonyms: 8-(β-D-Glucopyranosyl-7-hydroxy-3- (4-hydroxyphenyl)-4H-1-benzopyran-4-one; Puerarin; 8-(β-D-吡喃葡糖基-7-羟基-3-(4-羟苯基)-4H-1-苯并吡喃-4-酮; 葛根素

Database IDs

• CAS Number: 3681-99-0
• MDL Number: MFCD00076007
• Beilstein Number: 64198
• PubChem SID: 162225040; 24887971; 24898665
• PubChem CID: 5281807

CALCULATED PROPERTIES

• Acid pKa: 6.0298758
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -0.13829933
• LogD (pH = 7.4): -1.3562676
• Log P: -0.026883194
• Molar Refractivity: 102.8203 cm^3
• Polarizability: 40.101902 Å^3
• Polar Surface Area: 156.91 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• RTECS: UO5216000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: mouse ... Aldh1a2(19378), Maoa(17161)

Product Information

• Purity: ~80% (HPLC); ≥98.0% (HPLC); 99.0
• Grade: analytical standard, for drug analysis
• Empirical Formula (Hill Notation): C21H20O9

DETAILS

Sigma Aldrich - 82435

Biochem/physiol Actions
Isoflavone component of kudzu. Reduces anxiety symptoms associated with alcohol withdrawal.1