2-[(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methylidene]undecanoic acid

• ChemBase ID: 154365
• Molecular Formular: C21H30O6
• Molecular Mass: 378.4593
• Monoisotopic Mass: 378.20423868
• SMILES: CCCCCCCCC/C(=C\C1=C(C(=O)C(=C(C1=O)OC)OC)C)/C(=O)O
• Canonical SMILES: CCCCCCCCC/C(=C\C1=C(C)C(=O)C(=C(C1=O)OC)OC)/C(=O)O
• InChI: InChI=1S/C21H30O6/c1-5-6-7-8-9-10-11-12-15(21(24)25)13-16-14(2)17(22)19(26-3)20(27-4)18(16)23/h13H,5-12H2,1-4H3,(H,24,25)
• InChIKey: AALSSIXXBDPENJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methylidene]undecanoic acid
• IUPAC Traditional name: 2-[(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methylidene]undecanoic acid
• Synonyms: (2E)-2-[(4,5-Dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl)methylene]-undecanoic acid; E3330

Database IDs

• CAS Number: 136164-66-4
• MDL Number: MFCD00901331
• PubChem SID: 162248504
• PubChem CID: 6439397

CALCULATED PROPERTIES

• Acid pKa: 4.442563
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 3.4299245
• LogD (pH = 7.4): 1.6675417
• Log P: 4.522373
• Molar Refractivity: 106.306 cm^3
• Polarizability: 40.020622 Å^3
• Polar Surface Area: 89.9 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: red to orange powder

Safety Information

• GHS Hazard statements: H413
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H30O6

DETAILS

Sigma Aldrich - E8534

Biochem/physiol Actions
E3330 is a specific inhibitor of AP endonuclease 1 redox domain. E3330 inhibits APE-1 regulation of transcription factors, but does not affect Ape1 DNA repair activity. AP endonuclease 1 (APE1; also known as REF-1) is a multifunctional protein with dual functions in DNA repair and redox regulation of transcription factors. It is involved in apurinic/apyrimidinic endonuclease DNA base excision repair activity, in proofreading exonuclease activity, and in modulating DNA binding activity of several transcription factors including NF-κB, Egr-1, p53, AP-1, CREB, HIF-α, and members of the Pax family. APE1 is overexpressed in several human cancers, and disruption of APE1 function has detrimental effects on cancer cell viability. E3330 significantly reduces the growth of human pancreatic cancer cells in vitro and inhibits pancreatic cancer cell migration.