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

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
Accession Number
DB08613
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: 423.409
Monoisotopic: 423.086446698
Chemical Formula
C19H16F3N3O3S
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

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
24836810
PubChem Substance
99445084
ChemSpider
22378314
HET
TFG
PDB Entries
2vqj / 2vqo / 2vqq

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 Solubility0.116 mg/mLALOGPS
logP2.62ALOGPS
logP2.49ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)7.11ChemAxon
pKa (Strongest Basic)5.68ChemAxon
Physiological Charge0ChemAxon
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/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 / Benzene and substituted derivatives / N-substituted imidazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Fluorohydrins / Azacyclic compounds / Hydrocarbon derivatives
show 6 more
Substituents
5-phenylimidazole / 4-phenylimidazole / 2-heteroaryl carboxamide / Thiophene carboxamide / Thiophene carboxylic acid or derivatives / 2,5-disubstituted thiophene / Monocyclic benzene moiety / N-substituted imidazole / Benzenoid / Tertiary carboxylic acid amide
show 20 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 15:33 / Updated on December 01, 2017 16:07