NAV

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

Identification

Generic Name
(2E)-N-hydroxy-3-[1-methyl-4-(phenylacetyl)-1H-pyrrol-2-yl]prop-2-enamide
DrugBank Accession Number
DB07350
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 284.3098
Monoisotopic: 284.116092388
Chemical Formula
C16H16N2O3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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

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 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
Aromatic heteromonocyclic compound / Aryl alkyl ketone / Azacycle / Benzenoid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Hydroxamic acid / Monocyclic benzene moiety / N-methylpyrrole
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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

References

General References
Not Available
PubChem Compound
10379137
PubChem Substance
99443821
ChemSpider
8554580
ChEMBL
CHEMBL12760
ZINC
ZINC000013493184
PDBe Ligand
AGE

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 Solubility0.0539 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-MSsplash10-0006-9540000000-11e86bcfc6dd5b93e3c5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f79-0090000000-000c5e6d3050fee52867
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-750165e01116b32e0656
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ue9-1690000000-95a455088183100379a3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w29-2690000000-a236f85346d10cb9c7e9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001l-2930000000-15ea8e4e75aa5583ae56
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-6910000000-0f83bd70a476d53bbb98
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]-164.2415
predicted
DeepCCS 1.0 (2019)
[M+H]+166.5995
predicted
DeepCCS 1.0 (2019)
[M+Na]+172.69264
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Histone deacetylase 8
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. [Article]

Drug created at September 15, 2010 21:20 / Updated at June 12, 2020 16:52