5,7-dihydroxy-2-[4-hydroxy(3,5-2H2)phenyl](2H3)-4H-chromen-4-one

• ChemBase ID: 160753
• Molecular Formular: C15H10O5
• Molecular Mass: 270.2369
• Monoisotopic Mass: 270.05282342
• SMILES: c1(cc(c2c(c1)oc(cc2=O)c1ccc(cc1)O)O)O
• Canonical SMILES: Oc1ccc(cc1)c1cc(=O)c2c(o1)cc(cc2O)O
• InChI: InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H
• InChIKey: KZNIFHPLKGYRTM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-2-[4-hydroxy(3,5-^2H₂)phenyl](^2H₃)-4H-chromen-4-one
• IUPAC Traditional name: 5,7-dihydroxy-2-[4-hydroxy(3,5-^2H₂)phenyl](^2H₃)chromen-4-one
• Synonyms: Cyclo[(2S)-2-amino-8-oxodecanoyl-1-methoxy-L-tryptophyl-L-isoleucyl-(2R)-2-piperidinecarbonyl]; Cyclo(8-oxo-L-2-aminodecanoyl-1-methoxy-L-tryptophyl-L-isoleucyl-D-2-piperidinecarbonyl); Apicidin Ia; OSI 2040; Apicidin

Database IDs

• CAS Number: 183506-66-3
• PubChem SID: 162254888
• PubChem CID: 12358401

CALCULATED PROPERTIES

• Acid pKa: 6.6343265
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.6761353
• LogD (pH = 7.4): 1.8685302
• Log P: 2.7066891
• Molar Refractivity: 72.9139 cm^3
• Polarizability: 27.137085 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A726300

Apicidin is a potent (nM) cell permeable inhibitor of histone deacetylase. Also, Apicidin exhibits antiprotozoal and potential antimalarial properties. Apicidin has antiproliferative activity on HeLa cells accompanied by cell arrest at the G1 phase. Apici

REFERENCES

• Larsen, T., et al.: J. Microbiol. Methods, 24, 135 (1995)
• Bode, H., et al.: ChemBioChem., 3, 619 (1995)
• Nielsen, K., et al.: J. Agric. Food Chem., 53, 8190 (1995)