9-methoxy-2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium acetate hydrate

• ChemBase ID: 153209
• Molecular Formular: C21H24N2O4
• Molecular Mass: 368.42626
• Monoisotopic Mass: 368.17360726
• SMILES: Cc1c2cc[n+](cc2c(c2c1[nH]c1c2cc(cc1)OC)C)C.CC(=O)[O-].O
• Canonical SMILES: [O-]C(=O)C.COc1ccc2c(c1)c1c(C)c3c[n+](C)ccc3c(c1[nH]2)C.O
• InChI: InChI=1S/C19H18N2O.C2H4O2.H2O/c1-11-16-10-21(3)8-7-14(16)12(2)19-18(11)15-9-13(22-4)5-6-17(15)20-19;1-2(3)4;/h5-10H,1-4H3;1H3,(H,3,4);1H2
• InChIKey: HTBBZLKJMWASPB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-methoxy-2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium acetate hydrate
• IUPAC Traditional name: 9-methoxy-2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium acetate hydrate
• Synonyms: 9-Methoxy-2-methylellipticinium acetate hydrate; API-59CJ-Ome hydrate

Database IDs

• EC Number: 308-789-6
• MDL Number: MFCD08705317
• PubChem SID: 162247348; 24724403
• PubChem CID: 16078947

CALCULATED PROPERTIES

• Acid pKa: 14.841706
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -0.21150683
• LogD (pH = 7.4): -0.21150684
• Log P: -0.21150683
• Molar Refractivity: 90.4665 cm^3
• Polarizability: 37.93637 Å^3
• Polar Surface Area: 28.9 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥2 mg/mL, clear, dark red (with 5 min sonication); H2O: soluble1 mg/mL
• Apperance: red lyophilized powder

Safety Information

• Storage Condition: under inert gas
• German water hazard class: 3
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H19N2O · C2H3O2 · xH2O

DETAILS

Sigma Aldrich - A8979

Biochem/physiol Actions
API-59CJ-Ome hydrate is a highly selective Akt/PKB inhibitor. The PTEN (phosphatase and tensin homolog deleted on chromosome 10) tumor suppressor is mutated in 40-50% of human endometrial cancers. PTEN exerts its effects in part via inhibition of the antiapoptotic protein AKT. The endometrial cancer cell lines that express PTEN mutations show high levels of phosphorylated AKT and high AKT kinase activity. The endometrial cancer cell lines that express wild-type PTEN have little phosphorylated AKT and AKT kinase activity. API-59CJ-OMe inhibits AKT kinase activity and induces apoptosis in the cell lines with high AKT activity, but has little effect on cells without AKT activity. API-59CJ-OMe may therefore have therapeutic potential for those endometrial cancers that harbor PTEN mutations and AKT activation.