CAS 237430-03-4|Alsterpaullone|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^{12,17}]octadeca-1(1...

General Information

Structure

Molecular Formula

C₁₆H₁₁N₃O₃

Molecular Mass

293.27684

Exact Mass

293.08004123

Charge

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

Canonic Smiles

O=C1Nc2ccccc2-c2c(C1)c1cc(ccc1[nH]2)[N+](=O)[O-]

Isomeric Smiles

N1C(=O)Cc2c(c3c1cccc3)[nH]c1c2cc(cc1)[N+](=O)[O-]

Calculated Properties

JChem

LogD (pH = 7.4)

2.68

LogD (pH = 5.5)

2.68

Log P

2.68

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

13.11

Polar Surface Area

88.03

Polarizability

29.72

Molar Refractivity

82.01

LOG S

-5.03

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

AlsterpaulloneAlsterpaullone9-Nitro-7,12-dihydroindolo-[3,2-d][1]benzazepin-6(5)-one9-nitropaullonealsterpaullone9-nitro-7,12-dihydro-5H-indolo[3,2-d][1]benzazepin-6-one14-nitro-8,18-diazatetracyclo[9.7.0.0({2,7}).0({12,17})]octadeca-1(11),2,4,6,12(17),13,15-heptaen-9-one9-NITRO-5,12-DIHYDRO-7H-BENZO[2,3]AZEPINO[4,5-B]INDOL-6-ONE9-nitro-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-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 14-nitro-8,18-diazatetracyclo[9.7.0.0^{2,7}.0^{12,17}]octadeca-1(11),2,4,6,12,14,16-heptaen-9-one

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[9.7.0.0²,⁷.0¹²,¹⁷]octadeca-1(11),2,4,6,12,14,16-heptaen-9-one 14-nitro-8,18-diazatetracyclo[9.7.0.0²,⁷.0¹²,¹⁷]octadeca-1(11),2,4,6,12,14,16-heptaen-9-one

Names and Identifiers

Registration numbers

PubChem CID

5005498

PubChem SID

160967082248909184650473685338191

CAS Number

237430-03-4

MDL Number

MFCD02683579

PubMed Citation Links

10425100260617482644252520334651235772822205282112669310

Reaxys Registry

8340480

BKMS React Database

4990162584

CHEMBL

CHEMBL50894

BRENDA Database

2.7.11.132.7.11.262.7.10.22.7.11.222.7.11.12.7.11.241.1.1.372.7.11.11

LINCS Database

LSM-6558

Protein Data Bank

1q3w

SureChEMBL Database

SCHEMBL2170104

BRENDA Ligand Database

1625844990

PDBeChem Database

ATU

CHEBI ID

CHEBI:138488CHEBI:40939

BindingDB Database

CompTox Database

DrugBank ID

Chemspider ID

Registration numbers

Properties

Physical Property

Apperance

yellow to brown powder

Solubility

DMSO: ≥10 mg/mL

Pharmacology Properties

rat ... Gsk3b(84027)

Product Information

C16H11N3O3

≥98% (HPLC)

Properties

Related Proteins

PDB Bank

1Q3W

Related Proteins

Molecular Spectra

No Data Available

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Molecule 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.

ChEBI

CHEBI:138488

An organic heterotetracyclic compound that is 1,3-dihydro-2H-1-benzazepin-2-one which shares its 4-5 bond with the 3-2 bond of 5-nitro-1H-indole.

Molecule Details

References

PubChem Literature

No Data Available

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References

Bioactivity

PubChem BioAssay

Bioactivity