5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one

• ChemBase ID: 129154
• Molecular Formular: C16H12O5
• Molecular Mass: 284.26348
• Monoisotopic Mass: 284.06847348
• SMILES: COc1cc(c2c(c1)occ(c2=O)c1ccc(cc1)O)O
• Canonical SMILES: COc1cc(O)c2c(c1)occ(c2=O)c1ccc(cc1)O
• InChI: InChI=1S/C16H12O5/c1-20-11-6-13(18)15-14(7-11)21-8-12(16(15)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3
• InChIKey: KQMVAGISDHMXJJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one
• IUPAC Traditional name: prunetin
• Synonyms: Prunusetin; 4',5-dihydroxy-7-methoxyisoflavone; 5,4'-dihydroxy-7-methoxyisoflavone; Prunetin; 4′,5-Dihydroxy-7-methoxyisoflavone; Prunetin

Database IDs

• CAS Number: 552-59-0
• EC Number: 209-018-5
• MDL Number: MFCD00016951
• Beilstein Number: 292155
• PubChem SID: 162223451; 24887970
• PubChem CID: 5281804
• CHEMBL: 491174
• Wikipedia Title: Prunetin

CALCULATED PROPERTIES

• Acid pKa: 7.3233995
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.2163432
• LogD (pH = 7.4): 2.879653
• Log P: 3.2227664
• Molar Refractivity: 76.1652 cm^3
• Polarizability: 29.012989 Å^3
• Polar Surface Area: 75.99 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• RTECS: DJ3100050
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C16H12O5

DETAILS

Sigma Aldrich - 82415

Biochem/physiol Actions
Inhibitor of both cytoplasmic and mitochondrial human liver aldehyde dehydrogenases, possibly by binding at an allosteric site.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 82415.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.