N-hydroxy-5-[(3-phenyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)carbonyl]thiophene-2-carboxamide

Identification

Name
N-hydroxy-5-[(3-phenyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)carbonyl]thiophene-2-carboxamide
Accession Number
DB07879
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 368.41
Monoisotopic: 368.094311088
Chemical Formula
C18H16N4O3S
InChI Key
SMSIXMLQOONOQQ-UHFFFAOYSA-N
InChI
InChI=1S/C18H16N4O3S/c23-17(20-25)14-6-7-15(26-14)18(24)21-8-9-22-13(10-19-16(22)11-21)12-4-2-1-3-5-12/h1-7,10,25H,8-9,11H2,(H,20,23)
IUPAC Name
N-hydroxy-5-{3-phenyl-5H,6H,7H,8H-imidazo[1,2-a]pyrazine-7-carbonyl}thiophene-2-carboxamide
SMILES
ONC(=O)C1=CC=C(S1)C(=O)N1CCN2C(C1)=NC=C2C1=CC=CC=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UHistone deacetylase 4Not 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
24836811
PubChem Substance
99444350
ChemSpider
22377325
HET
HA3
PDB Entries
2vqm / 2vqv

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 Solubility0.346 mg/mLALOGPS
logP1.72ALOGPS
logP1.46ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)8.93ChemAxon
pKa (Strongest Basic)5.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area87.46 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity97.28 m3·mol-1ChemAxon
Polarizability38.73 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9967
Blood Brain Barrier+0.9106
Caco-2 permeable-0.7022
P-glycoprotein substrateSubstrate0.7234
P-glycoprotein inhibitor INon-inhibitor0.7827
P-glycoprotein inhibitor IINon-inhibitor0.9083
Renal organic cation transporterNon-inhibitor0.6892
CYP450 2C9 substrateNon-substrate0.8311
CYP450 2D6 substrateNon-substrate0.7245
CYP450 3A4 substrateNon-substrate0.5653
CYP450 1A2 substrateNon-inhibitor0.6148
CYP450 2C9 inhibitorInhibitor0.5621
CYP450 2D6 inhibitorNon-inhibitor0.8311
CYP450 2C19 inhibitorInhibitor0.5569
CYP450 3A4 inhibitorNon-inhibitor0.655
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8441
Ames testNon AMES toxic0.5234
CarcinogenicityNon-carcinogens0.8188
BiodegradationNot ready biodegradable0.975
Rat acute toxicity2.4885 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9801
hERG inhibition (predictor II)Inhibitor0.611
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 phenylimidazoles. These are polycyclic aromatic compounds containing a benzene ring linked to an imidazole ring through a CC or CN bond.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Imidazoles
Direct Parent
Phenylimidazoles
Alternative Parents
Thiophene carboxamides / 2-heteroaryl carboxamides / 2,5-disubstituted thiophenes / N-substituted imidazoles / Benzene and substituted derivatives / Tertiary carboxylic acid amides / Heteroaromatic compounds / Hydroxamic acids / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
4-phenylimidazole / 5-phenylimidazole / 2-heteroaryl carboxamide / Thiophene carboxylic acid or derivatives / Thiophene carboxamide / 2,5-disubstituted thiophene / Monocyclic benzene moiety / N-substituted imidazole / Benzenoid / Heteroaromatic compound
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an impo...
Gene Name
HDAC4
Uniprot ID
P56524
Uniprot Name
Histone deacetylase 4
Molecular Weight
119038.875 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 15:26 / Updated on December 01, 2017 15:57