(2E)-N-hydroxy-3-[1-methyl-4-(phenylacetyl)-1H-pyrrol-2-yl]prop-2-enamide

Identification

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Name
(2E)-N-hydroxy-3-[1-methyl-4-(phenylacetyl)-1H-pyrrol-2-yl]prop-2-enamide
Accession Number
DB07350
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: 284.3098
Monoisotopic: 284.116092388
Chemical Formula
C16H16N2O3
InChI Key
UFQOXIMRSMFQRI-BQYQJAHWSA-N
InChI
InChI=1S/C16H16N2O3/c1-18-11-13(10-14(18)7-8-16(20)17-21)15(19)9-12-5-3-2-4-6-12/h2-8,10-11,21H,9H2,1H3,(H,17,20)/b8-7+
IUPAC Name
(2E)-N-hydroxy-3-[1-methyl-4-(2-phenylacetyl)-1H-pyrrol-2-yl]prop-2-enamide
SMILES
CN1C=C(C=C1\C=C\C(=O)NO)C(=O)CC1=CC=CC=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UHistone deacetylase 8Not 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
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
10379137
PubChem Substance
99443821
ChemSpider
8554580
ChEMBL
CHEMBL12760
HET
AGE
PDB Entries
3f07

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 Solubility0.0539 mg/mLALOGPS
logP1.89ALOGPS
logP1.94ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.52ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area71.33 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity81.3 m3·mol-1ChemAxon
Polarizability30.18 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9761
Blood Brain Barrier+0.9612
Caco-2 permeable-0.5499
P-glycoprotein substrateNon-substrate0.7868
P-glycoprotein inhibitor INon-inhibitor0.8363
P-glycoprotein inhibitor IINon-inhibitor0.7896
Renal organic cation transporterNon-inhibitor0.8835
CYP450 2C9 substrateNon-substrate0.7686
CYP450 2D6 substrateNon-substrate0.8363
CYP450 3A4 substrateNon-substrate0.5865
CYP450 1A2 substrateNon-inhibitor0.7922
CYP450 2C9 inhibitorNon-inhibitor0.759
CYP450 2D6 inhibitorNon-inhibitor0.8849
CYP450 2C19 inhibitorNon-inhibitor0.6594
CYP450 3A4 inhibitorNon-inhibitor0.7922
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8112
Ames testNon AMES toxic0.5427
CarcinogenicityNon-carcinogens0.71
BiodegradationNot ready biodegradable0.9596
Rat acute toxicity2.4375 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9737
hERG inhibition (predictor II)Non-inhibitor0.8464
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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 aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbonyl compounds
Direct Parent
Aryl alkyl ketones
Alternative Parents
N-methylpyrroles / Benzene and substituted derivatives / Vinylogous amides / Heteroaromatic compounds / Hydroxamic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Aryl alkyl ketone / Monocyclic benzene moiety / N-methylpyrrole / Substituted pyrrole / Benzenoid / Vinylogous amide / Pyrrole / Heteroaromatic compound / Hydroxamic acid / Azacycle
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcription factor 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
HDAC8
Uniprot ID
Q9BY41
Uniprot Name
Histone deacetylase 8
Molecular Weight
41757.29 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 15:20 / Updated on June 04, 2019 06:39