(2S,3S,4S,5R,6R)-6-[(5,6-dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 72925
• Molecular Formular: C21H18O11
• Molecular Mass: 446.36102
• Monoisotopic Mass: 446.0849114
• SMILES: [C@@H]1([C@@H]([C@H]([C@H](O[C@@H]1C(=O)O)Oc1c(O)c(c2c(c1)oc(cc2=O)c1ccccc1)O)O)O)O
• Canonical SMILES: OC(=O)[C@H]1O[C@H](Oc2cc3oc(cc(=O)c3c(c2O)O)c2ccccc2)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H18O11/c22-9-6-10(8-4-2-1-3-5-8)30-11-7-12(14(23)15(24)13(9)11)31-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21,23-27H,(H,28,29)/t16-,17-,18+,19-,21-/m0/s1
• InChIKey: IKIIZLYTISPENI-UNJWAJPSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-[(5,6-dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-[(5,6-dihydroxy-4-oxo-2-phenylchromen-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: Baicalin

Database IDs

• CAS Number: 21967-41-9
• PubChem SID: 162037845
• PubChem CID: 13654833

CALCULATED PROPERTIES

• Acid pKa: 2.6182277
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -2.0355527
• LogD (pH = 7.4): -2.76751
• Log P: 0.7588956
• Molar Refractivity: 104.9257 cm^3
• Polarizability: 40.821663 Å^3
• Polar Surface Area: 183.21 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2269

Research Area: Neurological Disease
Biological Activity:
Baicalin is a known prolyl endopeptidase inhibitor and affects the GABA receptors. It is a flavone, a type of flavonoid. It is found in several species in the genus Scutellaria, including Scutellaria lateriflora (blue skullcap). There are 10 mg/g baicalin in Scutellaria galericulata (common skullcap) leaves. It is a component of Chinese medicinal herb Huang-chin(Scutellaria baicalensis). [1][2]

REFERENCES

• Tarragó T et al. Bioorg Med Chem. 2008 Aug 1;16(15):7516-24.