NAV

2,2,2-TRIFLUORO-1-{5-[(3-PHENYL-5,6-DIHYDROIMIDAZO[1,2-A]PYRAZIN-7(8H)-YL)CARBONYL]THIOPHEN-2-YL}ETHANE-1,1-DIOL

Identification

Generic Name
2,2,2-TRIFLUORO-1-{5-[(3-PHENYL-5,6-DIHYDROIMIDAZO[1,2-A]PYRAZIN-7(8H)-YL)CARBONYL]THIOPHEN-2-YL}ETHANE-1,1-DIOL
DrugBank Accession Number
DB08613
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 423.409
Monoisotopic: 423.086446698
Chemical Formula
C19H16F3N3O3S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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 / Benzene and substituted derivatives / N-substituted imidazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Fluorohydrins / Azacyclic compounds / Hydrocarbon derivatives
show 6 more
Substituents
2,5-disubstituted thiophene / 2-heteroaryl carboxamide / 4-phenylimidazole / 5-phenylimidazole / Alkyl fluoride / Alkyl halide / Aromatic alcohol / Aromatic heteropolycyclic compound / Azacycle / Benzenoid
show 20 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
OFBFUNBBOQCNFX-UHFFFAOYSA-N
InChI
InChI=1S/C19H16F3N3O3S/c20-19(21,22)18(27,28)15-7-6-14(29-15)17(26)24-8-9-25-13(10-23-16(25)11-24)12-4-2-1-3-5-12/h1-7,10,27-28H,8-9,11H2
IUPAC Name
2,2,2-trifluoro-1-(5-{3-phenyl-5H,6H,7H,8H-imidazo[1,2-a]pyrazine-7-carbonyl}thiophen-2-yl)ethane-1,1-diol
SMILES
OC(O)(C1=CC=C(S1)C(=O)N1CCN2C(C1)=NC=C2C1=CC=CC=C1)C(F)(F)F

References

General References
Not Available
PubChem Compound
24836810
PubChem Substance
99445084
ChemSpider
22378314
ZINC
ZINC000016052634
PDBe Ligand
TFG
PDB Entries
2vqj / 2vqo / 2vqq

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 Solubility0.116 mg/mLALOGPS
logP2.62ALOGPS
logP2.49Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)7.11Chemaxon
pKa (Strongest Basic)5.68Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area78.59 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity99.84 m3·mol-1Chemaxon
Polarizability40.36 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.7472
Caco-2 permeable-0.608
P-glycoprotein substrateSubstrate0.7256
P-glycoprotein inhibitor INon-inhibitor0.6789
P-glycoprotein inhibitor IINon-inhibitor0.6928
Renal organic cation transporterNon-inhibitor0.6351
CYP450 2C9 substrateNon-substrate0.7697
CYP450 2D6 substrateNon-substrate0.741
CYP450 3A4 substrateNon-substrate0.5568
CYP450 1A2 substrateNon-inhibitor0.6093
CYP450 2C9 inhibitorInhibitor0.6385
CYP450 2D6 inhibitorNon-inhibitor0.8507
CYP450 2C19 inhibitorInhibitor0.6207
CYP450 3A4 inhibitorNon-inhibitor0.671
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8609
Ames testNon AMES toxic0.713
CarcinogenicityNon-carcinogens0.9146
BiodegradationNot ready biodegradable0.9863
Rat acute toxicity2.7030 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9958
hERG inhibition (predictor II)Inhibitor0.7504
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/MSsplash10-00di-0000900000-bb2a5eb2389b9d239812
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fk9-0001900000-8ffc945b75dbfa433198
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0000900000-9991527446373d3f0cd3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uka-2604900000-e5ea8fb4b2e0fdeb9c2d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05fs-1940100000-0ded1a426ef775cac4a9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-0924000000-81bc5237e816c811bcca
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]-180.72292
predicted
DeepCCS 1.0 (2019)
[M+H]+183.08092
predicted
DeepCCS 1.0 (2019)
[M+Na]+189.33524
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 21:33 / Updated at June 12, 2020 16:52