6-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2H-pyran-2-one

• ChemBase ID: 132920
• Molecular Formular: C13H10O5
• Molecular Mass: 246.2155
• Monoisotopic Mass: 246.05282342
• SMILES: c1cc(c(cc1/C=C/c1cc(cc(=O)o1)O)O)O
• Canonical SMILES: Oc1cc(/C=C/c2ccc(c(c2)O)O)oc(=O)c1
• InChI: InChI=1S/C13H10O5/c14-9-6-10(18-13(17)7-9)3-1-8-2-4-11(15)12(16)5-8/h1-7,14-16H/b3-1+
• InChIKey: SGJNQVTUYXCBKH-HNQUOIGGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2H-pyran-2-one
• IUPAC Traditional name: hispidin
• Synonyms: 6-(3,4-dihydroxystyrl)-4-hydroxy-2-pyrone; Hispidin

Database IDs

• CAS Number: 555-55-5
• MDL Number: MFCD01866972
• PubChem SID: 24278468; 162227197
• PubChem CID: 54685921

CALCULATED PROPERTIES

• Acid pKa: 7.180883
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 1.9105713
• LogD (pH = 7.4): 1.4917473
• Log P: 1.9195318
• Molar Refractivity: 67.9513 cm^3
• Polarizability: 24.468294 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: yellow to brown solid

Safety Information

• Storage Condition: protect from light
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... PRKACB(5567), PRKAR2B(5577), PRKCB(5579)

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - H5257

Biochem/physiol Actions
Potent inhibitor of protein kinase Cβ, cytotoxic for cancer cells.