8,11-dihydroxy-4-(2-hydroxyethyl)-6-({2-[(2-hydroxyethyl)amino]ethyl}amino)-1,2,3,4,7,12-hexahydro-1,4-diazatetraphene-7,12-dione

• ChemBase ID: 174656
• Molecular Formular: C22H26N4O6
• Molecular Mass: 442.46504
• Monoisotopic Mass: 442.18523457
• SMILES: c1(ccc(c2c1C(=O)c1c(C2=O)c2c(cc1NCCNCCO)N(CCN2)CCO)O)O
• Canonical SMILES: OCCNCCNc1cc2N(CCO)CCNc2c2c1C(=O)c1c(C2=O)c(O)ccc1O
• InChI: InChI=1S/C22H26N4O6/c27-9-6-23-3-4-24-12-11-13-20(25-5-7-26(13)8-10-28)19-16(12)21(31)17-14(29)1-2-15(30)18(17)22(19)32/h1-2,11,23-25,27-30H,3-10H2
• InChIKey: GJMHXLAWJIOZMT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8,11-dihydroxy-4-(2-hydroxyethyl)-6-({2-[(2-hydroxyethyl)amino]ethyl}amino)-1,2,3,4,7,12-hexahydro-1,4-diazatetraphene-7,12-dione
• IUPAC Traditional name: 8,11-dihydroxy-4-(2-hydroxyethyl)-6-({2-[(2-hydroxyethyl)amino]ethyl}amino)-2,3-dihydro-1H-1,4-diazatetraphene-7,12-dione
• Synonyms: 1,2,3,4-Tetrahydro-8,11-dihydroxy-4-(2-hydroxyethyl)-6-[[2-[(2-hydroxyethyl)amino]ethyl]amino]naphtho[2,3-f]quinoxaline-7,12-dione; Mitoxantrone Impurity D; Mitoxantrone (2-Hydroxyethyl)piperazine Impurity(Mitoxantrone Impurity D)

Database IDs

• CAS Number: 137132-70-8
• PubChem SID: 164230566
• PubChem CID: 132032

CALCULATED PROPERTIES

• Acid pKa: 9.721892
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -0.9579377
• LogD (pH = 7.4): 0.57296854
• Log P: 1.7270659
• Molar Refractivity: 123.269 cm^3
• Polarizability: 44.771217 Å^3
• Polar Surface Area: 154.39 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Dark Blue Solid
• Melting Point: 175-179°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M373435

A metabolite of the anticancer agent Mitoxantrone (M373425)

REFERENCES

• Feafanov, A. et al.: Anticcancer Res., 19, 5341 (1999)
• Ponousis, C. et al.: Biochem. Pharmacol., 48, 2223 (1999)