11-oxo-3,10-diazapentacyclo[10.7.1.02,10.04,9.016,20]icosa-1(20),2,4(9),5,7,12,14,16,18-nonaene-17-carboxylic acid; acetic acid

• ChemBase ID: 154535
• Molecular Formular: C21H14N2O5
• Molecular Mass: 374.34626
• Monoisotopic Mass: 374.09027156
• SMILES: CC(=O)O.c1ccc2c(c1)nc1n2c(=O)c2cccc3c2c1ccc3C(=O)O
• Canonical SMILES: OC(=O)c1ccc2c3c1cccc3c(=O)n1c2nc2c1cccc2.CC(=O)O
• InChI: InChI=1S/C19H10N2O3.C2H4O2/c22-18-13-5-3-4-10-11(19(23)24)8-9-12(16(10)13)17-20-14-6-1-2-7-15(14)21(17)18;1-2(3)4/h1-9H,(H,23,24);1H3,(H,3,4)
• InChIKey: WNRSTFUVBWNELX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 11-oxo-3,10-diazapentacyclo[10.7.1.0^2,^1^0.0^4,^9.0^1^6,^2^0]icosa-1(20),2,4(9),5,7,12,14,16,18-nonaene-17-carboxylic acid; acetic acid
• IUPAC Traditional name: 11-oxo-3,10-diazapentacyclo[10.7.1.0^2,^1^0.0^4,^9.0^1^6,^2^0]icosa-1(20),2,4(9),5,7,12,14,16,18-nonaene-17-carboxylic acid; acetic acid
• Synonyms: 7-Oxo-7H-benzimidazo[2,1-a]benz[de]isoquinoline-3-carboxylic acid - acetic acid; STO-609-acetic acid

Database IDs

• MDL Number: MFCD06411456
• PubChem SID: 162248674
• PubChem CID: 16760660

CALCULATED PROPERTIES

• Acid pKa: 3.3914957
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.0363332
• LogD (pH = 7.4): -0.2729868
• Log P: 3.1320717
• Molar Refractivity: 97.6593 cm^3
• Polarizability: 35.947342 Å^3
• Polar Surface Area: 72.19 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble15 mg/mL at ≥60 °C
• Apperance: solid
• Melting Point: >300 °C

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C19H10N2O3 · C2H4O2

DETAILS

Sigma Aldrich - S1318

General description
1:1 adduct with acetic acid
Biochem/physiol Actions
Selective Ca2+/Calmodulin-dependent protein kinase kinase (CaM-KK) antagonist. Inhibits CamKKa and CaMKKb with Ki = 80 and 15 ng/mL, respectively. Does not inhibit downstream CaM kinases (CaMKI and CaMKIV).