1-amino-5,8-dihydroxy-4-({2-[(2-hydroxyethyl)amino]ethyl}amino)-9,10-dihydroanthracene-9,10-dione

• ChemBase ID: 166288
• Molecular Formular: C18H19N3O5
• Molecular Mass: 357.36056
• Monoisotopic Mass: 357.13247072
• SMILES: c1(ccc(c2c1C(=O)c1c(C2=O)c(ccc1NCCNCCO)N)O)O
• Canonical SMILES: OCCNCCNc1ccc(c2c1C(=O)c1c(C2=O)c(O)ccc1O)N
• InChI: InChI=1S/C18H19N3O5/c19-9-1-2-10(21-6-5-20-7-8-22)14-13(9)17(25)15-11(23)3-4-12(24)16(15)18(14)26/h1-4,20-24H,5-8,19H2
• InChIKey: NBSLQRRHRCDIHJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-amino-5,8-dihydroxy-4-({2-[(2-hydroxyethyl)amino]ethyl}amino)-9,10-dihydroanthracene-9,10-dione
• IUPAC Traditional name: 1-amino-5,8-dihydroxy-4-({2-[(2-hydroxyethyl)amino]ethyl}amino)anthracene-9,10-dione
• Synonyms: 1-Amino-5,8-dihydroxy-4-[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedione; Mitoxantrone Impurity A; Des[2-[(2-Hydroxyethyl)amino]ethyl] Mitoxantrone(Mitoxantrone Impurity A)

Database IDs

• CAS Number: 89991-52-6
• PubChem SID: 162260421
• PubChem CID: 13276605

CALCULATED PROPERTIES

• Acid pKa: 9.719584
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -0.49990565
• LogD (pH = 7.4): 1.0239211
• Log P: 2.1780155
• Molar Refractivity: 99.0237 cm^3
• Polarizability: 36.347885 Å^3
• Polar Surface Area: 144.91 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Dark Blue Solid
• Melting Point: >300°C

Safety Information

• Storage Condition: Refrigerator, under inert atmosphere

DETAILS

Toronto Research Chemicals - D290005

An impurity of the anticancer agent Mitoxantrone (M373425) used in immunosuppresion studies.

REFERENCES

• Wang, S. et al.: Int. J. Immunopharmacol., 9, 733 (1987)