H-89

Identification

Generic Name

H-89

DrugBank Accession Number

DB07995

Background

Not Available

Type

Small Molecule

Groups

Experimental

Structure

Similar Structures

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

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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings

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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	inhibitor	Humans

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

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Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">: 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

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 / 3vqh

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0002-0100900000-b6cd4078edacce449425
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-0001900000-a77ac625e748afd696b4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0007-0940400000-e7228d3e9698a9fa03c1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-002f-5650900000-29c104b69ad4147fbd9f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0159-0900000000-f317e45cbfbdcc44dabb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004i-2900000000-df58cc0da774699651af
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	188.22646	predicted	DeepCCS 1.0 (2019)
[M+H]+	190.58444	predicted	DeepCCS 1.0 (2019)
[M+Na]+	197.42982	predicted	DeepCCS 1.0 (2019)

Targets

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Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	48	N/A	30	A30972

Details1. cAMP-dependent protein kinase catalytic subunit alpha

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]

Details2. cAMP-dependent protein kinase inhibitor alpha

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]

Details3. Serine/threonine-protein kinase haspin

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]

Details4. Interferon-induced, double-stranded RNA-activated protein kinase

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

H-89

Identification

Structure for H-89 (DB07995)

Pharmacology

Interactions

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

References

References