N-[2-(4-BROMOCINNAMYLAMINO)ETHYL]-5-ISOQUINOLINE SULFONAMIDE

Identification

Name
N-[2-(4-BROMOCINNAMYLAMINO)ETHYL]-5-ISOQUINOLINE SULFONAMIDE
Accession Number
DB07995
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
M876330O56
CAS number
Not Available
Weight
Average: 446.361
Monoisotopic: 445.045960236
Chemical Formula
C20H20BrN3O2S
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UcAMP-dependent protein kinase catalytic subunit alphaNot AvailableHuman
UcAMP-dependent protein kinase inhibitor alphaNot AvailableHuman
USerine/threonine-protein kinase haspinNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
449241
PubChem Substance
99444466
ChemSpider
395827
BindingDB
15211
ChEBI
47495
ChEMBL
CHEMBL104264
HET
IQB
PDB Entries
1ydt / 3fmd / 3vqh

Clinical Trials

Clinical Trials
Not Available

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
PropertyValueSource
Water Solubility0.00118 mg/mLALOGPS
logP2.7ALOGPS
logP3.23ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)10.04ChemAxon
pKa (Strongest Basic)8.1ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area71.09 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity112.68 m3·mol-1ChemAxon
Polarizability43.91 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9928
Blood Brain Barrier+0.8775
Caco-2 permeable-0.6253
P-glycoprotein substrateSubstrate0.7137
P-glycoprotein inhibitor IInhibitor0.6202
P-glycoprotein inhibitor IINon-inhibitor0.7667
Renal organic cation transporterNon-inhibitor0.6484
CYP450 2C9 substrateNon-substrate0.8031
CYP450 2D6 substrateNon-substrate0.8063
CYP450 3A4 substrateNon-substrate0.5984
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.5483
CYP450 2C19 inhibitorInhibitor0.5421
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8006
Ames testNon AMES toxic0.6574
CarcinogenicityNon-carcinogens0.832
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6331 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.6016
hERG inhibition (predictor II)Inhibitor0.5127
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Isoquinoline / Styrene / Bromobenzene / Halobenzene / Aryl bromide / Aryl halide / Monocyclic benzene moiety / Pyridine / Organosulfonic acid amide / Benzenoid
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:10592235]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:10592235]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:10592235]

Drug created on September 15, 2010 15:27 / Updated on December 01, 2017 15:58