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

• ChemBase ID: 154826
• Molecular Formular: C22H28N4O4
• Molecular Mass: 412.48212
• Monoisotopic Mass: 412.2110554
• SMILES: CN(C)CCNc1ccc(c2c1C(=O)c1c(ccc(c1C2=O)O)O)NCCN(C)C
• Canonical SMILES: CN(CCNc1ccc(c2c1C(=O)c1c(C2=O)c(O)ccc1O)NCCN(C)C)C
• InChI: InChI=1S/C22H28N4O4/c1-25(2)11-9-23-13-5-6-14(24-10-12-26(3)4)18-17(13)21(29)19-15(27)7-8-16(28)20(19)22(18)30/h5-8,23-24,27-28H,9-12H2,1-4H3
• InChIKey: DBAMBJQJKDHEQX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4-bis({[2-(dimethylamino)ethyl]amino})-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione
• IUPAC Traditional name: 1,4-bis({[2-(dimethylamino)ethyl]amino})-5,8-dihydroxyanthracene-9,10-dione
• Synonyms: 1,4-Bis[[2-(dimethylamino)ethyl]amino]-5,8-dihydroxy-9,10-anthracenedione; 1,4-Bis[[2-(dimethylamino)ethyl]amino]-5,8-dihydroxyanthracene-9,10-dione; AQ4

Database IDs

• CAS Number: 70476-63-0
• MDL Number: MFCD02656425
• PubChem SID: 162248964
• PubChem CID: 135468

CALCULATED PROPERTIES

• Acid pKa: 9.659531
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.07586288
• LogD (pH = 7.4): 3.191027
• Log P: 3.8944206
• Molar Refractivity: 121.5386 cm^3
• Polarizability: 44.5837 Å^3
• Polar Surface Area: 105.14 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: dark blue powder

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 22-50/53
• Safety Statements: 22-60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H410
• GHS Precautionary statements: P273-P501
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H28N4O4

DETAILS

Sigma Aldrich - A9236

Biochem/physiol Actions
AQ4 is a chemically stable cytotoxic agent which acts as a topoisomerase II inhibitor and DNA intercalator. The compound is a potent cytotoxic agent in many human tumor lines, including those derived from human pancreatic adenocarcinomas. The compound N-oxide is a hypoxia activated prodrug of topoisomerase-targeting.