14-nitro-8,18-diazatetracyclo[9.7.0.0^{2,7}.0^{12,17}]octadeca-1(11),2(7),3,5,12,14,16-heptaen-9-one

• ChemBase ID: 3644
• Molecular Formular: C16H11N3O3
• Molecular Mass: 293.27684
• Monoisotopic Mass: 293.08004123
• SMILES: N1C(=O)Cc2c(c3c1cccc3)[nH]c1c2cc(cc1)[N+](=O)[O-]
• Canonical SMILES: O=C1Nc2ccccc2c2c(C1)c1cc(ccc1[nH]2)[N+](=O)[O-]
• InChI: InChI=1S/C16H11N3O3/c20-15-8-12-11-7-9(19(21)22)5-6-14(11)18-16(12)10-3-1-2-4-13(10)17-15/h1-7,18H,8H2,(H,17,20)
• InChIKey: OLUKILHGKRVDCT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 14-nitro-8,18-diazatetracyclo[9.7.0.0^{2,7}.0^{12,17}]octadeca-1(11),2(7),3,5,12,14,16-heptaen-9-one; 14-nitro-8,18-diazatetracyclo[9.7.0.0^2,^7.0^1^2,^1^7]octadeca-1(11),2,4,6,12,14,16-heptaen-9-one
• IUPAC Traditional name: 14-nitro-8,18-diazatetracyclo[9.7.0.0^{2,7}.0^{12,17}]octadeca-1(11),2(7),3,5,12,14,16-heptaen-9-one; alsterpaullone
• Synonyms: Alsterpaullone; 9-Nitro-7,12-dihydroindolo-[3,2-d][1]benzazepin-6(5)-one; Alsterpaullone

Database IDs

• CAS Number: 237430-03-4
• MDL Number: MFCD02683579
• PubChem SID: 24890918; 46504736; 160967082
• PubChem CID: 5005498

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.448507
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.6780229
• LogD (pH = 7.4): 2.6780193
• Log P: 2.6780229
• Molar Refractivity: 83.0098 cm^3
• Polarizability: 32.483665 Å^3
• Polar Surface Area: 90.71 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.07
• LOG S: -4.09
• Solubility (Water): 2.37e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: yellow to brown powder

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: rat ... Gsk3b(84027)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C16H11N3O3

DETAILS

DrugBank - DB04014

Drug information: experimental

Sigma Aldrich - A4847

Biochem/physiol Actions
Potent and selective inhibitor of GSK-3β and CDK5/p25; potent inhibitor of CDK1/cyclin B (IC50 = 0.035 μM).
Application
Alsterpaullone inhibits GSK-3β, CDK5/p25, and CDK1/cyclin B. Alsterpaullone has also been studied as an antimanic therapeutic for the acute manic phase of bipolar disorder.