2-[2,6-dihydroxy-4-({[(3R,4R)-3-(4-hydroxybenzamido)azepan-4-yl]oxy}carbonyl)benzoyl]-3-hydroxybenzoic acid

• ChemBase ID: 161103
• Molecular Formular: C28H26N2O10
• Molecular Mass: 550.51344
• Monoisotopic Mass: 550.15874504
• SMILES: C1[C@H]([C@@H](CNCC1)NC(=O)c1ccc(cc1)O)OC(=O)c1cc(c(c(c1)O)C(=O)c1c(cccc1O)C(=O)O)O
• Canonical SMILES: Oc1ccc(cc1)C(=O)N[C@@H]1CNCCC[C@H]1OC(=O)c1cc(O)c(c(c1)O)C(=O)c1c(O)cccc1C(=O)O
• InChI: InChI=1S/C28H26N2O10/c31-16-8-6-14(7-9-16)26(36)30-18-13-29-10-2-5-22(18)40-28(39)15-11-20(33)24(21(34)12-15)25(35)23-17(27(37)38)3-1-4-19(23)32/h1,3-4,6-9,11-12,18,22,29,31-34H,2,5,10,13H2,(H,30,36)(H,37,38)/t18-,22-/m1/s1
• InChIKey: XYUFCXJZFZPEJD-XMSQKQJNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2,6-dihydroxy-4-({[(3R,4R)-3-(4-hydroxybenzamido)azepan-4-yl]oxy}carbonyl)benzoyl]-3-hydroxybenzoic acid
• IUPAC Traditional name: 2-[2,6-dihydroxy-4-({[(3R,4R)-3-(4-hydroxybenzamido)azepan-4-yl]oxy}carbonyl)benzoyl]-3-hydroxybenzoic acid
• Synonyms: 4-(2-Carboxy-6-hydroxybenzoyl)-3,5-dihydroxybenzoic Acid (3R,4R)-Hexahydro-3-[(4-hydroxybenzoyl)amino]-1H-azepin-4-yl Ester; (3R-trans)-Balanol; (-)-Balanol; Azepinostatin; Ophiocordin; Balanol

Database IDs

• CAS Number: 63590-19-2
• PubChem SID: 162255238
• PubChem CID: 5287736

CALCULATED PROPERTIES

• Acid pKa: 2.9757955
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): 2.3900511
• LogD (pH = 7.4): 2.091101
• Log P: 2.3908398
• Molar Refractivity: 141.5085 cm^3
• Polarizability: 53.72256 Å^3
• Polar Surface Area: 202.72 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B115500

Balanol, a fungal metabolite, is a potent ATP-competitive inhibitor of Protein Kinase C (PKC) and Protein Kinase A (PKA), important targets in oncology.

REFERENCES

• Crane, H., et al.: Bioorg. Med. Chem. Lett., 5, 2133 (1995)
• Lai, Y., et al.: J. Med. Chem., 40, 226 (1995)
• Narayana, N., et al.: Biochemistry, 38, 2367 (1995)