NAV

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

Identification

Generic Name
N-hydroxy-5-[(3-phenyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)carbonyl]thiophene-2-carboxamide
DrugBank Accession Number
DB07879
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 368.41
Monoisotopic: 368.094311088
Chemical Formula
C18H16N4O3S
Synonyms
Not Available
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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
TargetActionsOrganism
UHistone deacetylase 4Not AvailableHumans
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
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
Not Available
Chemical TaxonomyProvided by Classyfire
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
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Substituents
2,5-disubstituted thiophene / 2-heteroaryl carboxamide / 4-phenylimidazole / 5-phenylimidazole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carboxamide group / Carboxylic acid derivative / Heteroaromatic compound
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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

References

General References
Not Available
PubChem Compound
24836811
PubChem Substance
99444350
ChemSpider
22377325
ZINC
ZINC000016052633
PDBe Ligand
HA3
PDB Entries
2vqm / 2vqv

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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)8.38Chemaxon
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/MSsplash10-014r-0009000000-fbfc7854a3dac6ca6de5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-066r-0009000000-01c39289719d69188815
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-d9d7850b896958d36358
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00ls-2409000000-1d9f4c906f2f5e948610
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ku-0669000000-40cec82d2e6e5f180df3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-053s-6922000000-2ea1c02aed85f716f84a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-175.36531
predicted
DeepCCS 1.0 (2019)
[M+H]+177.81688
predicted
DeepCCS 1.0 (2019)
[M+Na]+185.52986
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Histone deacetylase 4
Kind
Protein
Organism
Humans
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. [Article]

Drug created at September 15, 2010 21:26 / Updated at June 12, 2020 16:52