Identification
- Generic Name
- H-89
- DrugBank Accession Number
- DB07995
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for H-89 (DB07995)
- Weight
- Average: 446.361
Monoisotopic: 445.045960236 - Chemical Formula
- C20H20BrN3O2S
- Synonyms
- N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide
- External IDs
- H 89
- H-89
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UcAMP-dependent protein kinase catalytic subunit alpha Not Available Humans UcAMP-dependent protein kinase inhibitor alpha Not Available Humans USerine/threonine-protein kinase haspin Not Available Humans UInterferon-induced, double-stranded RNA-activated protein kinase inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Isoquinolines and derivatives
- Sub Class
- Not Available
- Direct Parent
- Isoquinolines and derivatives
- Alternative Parents
- Styrenes / Bromobenzenes / Pyridines and derivatives / Organosulfonamides / Aryl bromides / Heteroaromatic compounds / Aminosulfonyl compounds / Dialkylamines / Azacyclic compounds / Organopnictogen compounds show 3 more
- Substituents
- Amine / Aminosulfonyl compound / Aromatic heteropolycyclic compound / Aryl bromide / Aryl halide / Azacycle / Benzenoid / Bromobenzene / Halobenzene / Heteroaromatic compound show 19 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- M876330O56
- CAS number
- 127243-85-0
- InChI Key
- ZKZXNDJNWUTGDK-NSCUHMNNSA-N
- 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+
- IUPAC Name
- N-(2-{[(2E)-3-(4-bromophenyl)prop-2-en-1-yl]amino}ethyl)isoquinoline-5-sulfonamide
- SMILES
- BrC1=CC=C(\C=C\CNCCNS(=O)(=O)C2=CC=CC3=C2C=CN=C3)C=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 449241
- PubChem Substance
- 99444466
- ChemSpider
- 395827
- BindingDB
- 15211
- ChEBI
- 47495
- ChEMBL
- CHEMBL104264
- ZINC
- ZINC000002043204
- PDBe Ligand
- IQB
- Wikipedia
- H-89
- PDB Entries
- 1ydt / 3fmd / 3vqh
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00118 mg/mL ALOGPS logP 2.7 ALOGPS logP 3.23 Chemaxon logS -5.6 ALOGPS pKa (Strongest Acidic) 10.04 Chemaxon pKa (Strongest Basic) 8.1 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 71.09 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 112.68 m3·mol-1 Chemaxon Polarizability 43.91 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9928 Blood Brain Barrier + 0.8775 Caco-2 permeable - 0.6253 P-glycoprotein substrate Substrate 0.7137 P-glycoprotein inhibitor I Inhibitor 0.6202 P-glycoprotein inhibitor II Non-inhibitor 0.7667 Renal organic cation transporter Non-inhibitor 0.6484 CYP450 2C9 substrate Non-substrate 0.8031 CYP450 2D6 substrate Non-substrate 0.8063 CYP450 3A4 substrate Non-substrate 0.5984 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.5483 CYP450 2C19 inhibitor Inhibitor 0.5421 CYP450 3A4 inhibitor Inhibitor 0.7959 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8006 Ames test Non AMES toxic 0.6574 Carcinogenicity Non-carcinogens 0.832 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.6331 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.6016 hERG inhibition (predictor II) Inhibitor 0.5127
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ubiquitin protein ligase binding
- Specific Function
- Phosphorylates a large number of substrates in the cytoplasm and the nucleus. Regulates the abundance of compartmentalized pools of its regulatory subunits through phosphorylation of PJA2 which bin...
- Gene Name
- PRKACA
- Uniprot ID
- P17612
- Uniprot Name
- cAMP-dependent protein kinase catalytic subunit alpha
- Molecular Weight
- 40589.38 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Protein kinase a catalytic subunit binding
- Specific Function
- Extremely potent competitive inhibitor of cAMP-dependent protein kinase activity, this protein interacts with the catalytic subunit of the enzyme after the cAMP-induced dissociation of its regulato...
- Gene Name
- PKIA
- Uniprot ID
- P61925
- Uniprot Name
- cAMP-dependent protein kinase inhibitor alpha
- Molecular Weight
- 7988.435 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Protein kinase activity
- Specific Function
- Serine/threonine-protein kinase that phosphorylates histone H3 at 'Ser-3' (H3T3ph) during mitosis. This positions and activates AURKB and other components of the chromosomal passenger complex (CPC)...
- Gene Name
- GSG2
- Uniprot ID
- Q8TF76
- Uniprot Name
- Serine/threonine-protein kinase haspin
- Molecular Weight
- 88494.565 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- IFN-induced dsRNA-dependent serine/threonine-protein kinase which plays a key role in the innate immune response to viral infection and is also involved in the regulation of signal transduction, apoptosis, cell proliferation and differentiation. Exerts its antiviral activity on a wide range of DNA and RNA viruses including hepatitis C virus (HCV), hepatitis B virus (HBV), measles virus (MV) and herpes simplex virus 1 (HHV-1). Inhibits viral replication via phosphorylation of the alpha subunit of eukaryotic initiation factor 2 (EIF2S1), this phosphorylation impairs the recycling of EIF2S1 between successive rounds of initiation leading to inhibition of translation which eventually results in shutdown of cellular and viral protein synthesis. Also phosphorylates other substrates including p53/TP53, PPP2R5A, DHX9, ILF3, IRS1 and the HHV-1 viral protein US11. In addition to serine/threonine-protein kinase activity, also has tyrosine-protein kinase activity and phosphorylates CDK1 at 'Tyr-4' upon DNA damage, facilitating its ubiquitination and proteosomal degradation. Either as an adapter protein and/or via its kinase activity, can regulate various signaling pathways (p38 MAP kinase, NF-kappa-B and insulin signaling pathways) and transcription factors (JUN, STAT1, STAT3, IRF1, ATF3) involved in the expression of genes encoding proinflammatory cytokines and IFNs. Activates the NF-kappa-B pathway via interaction with IKBKB and TRAF family of proteins and activates the p38 MAP kinase pathway via interaction with MAP2K6. Can act as both a positive and negative regulator of the insulin signaling pathway (ISP). Negatively regulates ISP by inducing the inhibitory phosphorylation of insulin receptor substrate 1 (IRS1) at 'Ser-312' and positively regulates ISP via phosphorylation of PPP2R5A which activates FOXO1, which in turn up-regulates the expression of insulin receptor substrate 2 (IRS2). Can regulate NLRP3 inflammasome assembly and the activation of NLRP3, NLRP1, AIM2 and NLRC4 inflammasomes. Can trigger apoptosis via FADD-mediated activation of CASP8. Plays a role in the regulation of the cytoskeleton by binding to gelsolin (GSN), sequestering the protein in an inactive conformation away from actin.
- Specific Function
- Atp binding
- Gene Name
- EIF2AK2
- Uniprot ID
- P19525
- Uniprot Name
- Interferon-induced, double-stranded RNA-activated protein kinase
- Molecular Weight
- 62093.71 Da
References
- Harrison PK, Connor M, Kelly E: Chronic ethanol promotes the neuronal differentiation of NG108-15 cells independently of toxin-sensitive G-proteins. Environ Toxicol Pharmacol. 1997 Sep;3(4):307-19. doi: 10.1016/s1382-6689(97)00023-9. [Article]
Drug created at September 15, 2010 21:27 / Updated at June 24, 2022 21:36