N-(2-{[(2E)-3-(4-bromophenyl)prop-2-en-1-yl]amino}ethyl)isoquinoline-5-sulfonamide

• ChemBase ID: 5624
• Molecular Formular: C20H20BrN3O2S
• Molecular Mass: 446.3607
• Monoisotopic Mass: 445.0459599
• SMILES: c1(cccc2cnccc12)S(=O)(=O)NCCNC/C=C/c1ccc(Br)cc1
• Canonical SMILES: Brc1ccc(cc1)/C=C/CNCCNS(=O)(=O)c1cccc2c1ccnc2
• InChI: InChI=1S/C20H20BrN3O2S/c21-18-8-6-16(7-9-18)3-2-11-22-13-14-24-27(25,26)20-5-1-4-17-15-23-12-10-19(17)20/h1-10,12,15,22,24H,11,13-14H2/b3-2+
• InChIKey: ZKZXNDJNWUTGDK-NSCUHMNNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2-{[(2E)-3-(4-bromophenyl)prop-2-en-1-yl]amino}ethyl)isoquinoline-5-sulfonamide; N-(2-{[3-(4-bromophenyl)prop-2-en-1-yl]amino}ethyl)isoquinoline-5-sulfonamide
• IUPAC Traditional name: N-(2-{[(2E)-3-(4-bromophenyl)prop-2-en-1-yl]amino}ethyl)isoquinoline-5-sulfonamide; N-(2-{[3-(4-bromophenyl)prop-2-en-1-yl]amino}ethyl)isoquinoline-5-sulfonamide
• Synonyms: N-[2-[[3-(4-Bromophenyl)-2-propen-1-yl]amino]ethyl]-5-isoquinolinesulfonamide; H-89; N-[2-(p-Bromocinnamylamino)ethyl]-5-Isoquinoline Sulfonamide; N-[2-[[3-(4-Bromophenyl)-2-propen-1-yl]amino]ethyl]-5-isoquinolinesulfonamide Hydrochloride; N-[2-(p-Bromocinnamylamino)ethyl]-5-isoquinoline Sulfonamide Dihydrochloride; N-[2-(4-BROMOCINNAMYLAMINO)ETHYL]-5-ISOQUINOLINE SULFONAMIDE; H-89

Database IDs

• CAS Number: 127243-85-0; 130964-39-5
• PubChem SID: 99444466; 160969052
• PubChem CID: 449241
• Chemspider ID: 395827
• Wikipedia Title: H-89

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.041068
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.7977911
• LogD (pH = 7.4): 2.5343072
• Log P: 3.2284625
• Molar Refractivity: 112.6843 cm^3
• Polarizability: 45.041603 Å^3
• Polar Surface Area: 71.09 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.7
• LOG S: -5.58
• Solubility (Water): 1.18e-03 g/l

PROPERTIES

Physical Property

• Solubility: Choroform; Dichloromethane; Methanol; Soluble to 25 mM in water; up to 100 mM DMSO; Water
• Apperance: White Solid; White to Off-White Solid
• Melting Point: 127-129°C; 195-200°C

Safety Information

• Storage Condition: -20°C Freezer
• Safety Statements: S22 - Do not breathe dust; S24/25 - Avoid contact with skin and eyes; S36/37/39 - Wear suitable protective clothing, gloves andeye/face protection
• Main Hazard: Exposure may cause irritation to eyes, mucous membranes, upperrespiratory tract and skin.

DETAILS

DrugBank - DB07995

Drug information: experimental

Toronto Research Chemicals - B682440

Selective inhibitor of Protein Kinase A (cyclic AMP-dependeant Protein Kinase) with an inhibitory constant of 0.0048 uM.

Toronto Research Chemicals - B682445

Selective inhibitor of Protein Kinase A (cyclic AMP-dependeant Protein Kinase) with an inhibitory constant of 0.0048 uM.

REFERENCES

• Chijiwa, T. et al.: J. Bio. Chem., 265 (9)
• 5267-5272 (1990)
• Chijiwa, T. et al.: J. Bio. Chem., 265 (9)
• 5267-5272 (1990)