NAV

4-{(1E)-3-OXO-3-[(2-PHENYLETHYL)AMINO]PROP-1-EN-1-YL}-1,2-PHENYLENE DIACETATE

Identification

Generic Name
4-{(1E)-3-OXO-3-[(2-PHENYLETHYL)AMINO]PROP-1-EN-1-YL}-1,2-PHENYLENE DIACETATE
DrugBank Accession Number
DB08753
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 367.3951
Monoisotopic: 367.141972787
Chemical Formula
C21H21NO5
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
UPeptide deformylaseNot AvailableHelicobacter pylori
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 cinnamic acid amides. These are amides of cinnamic acids. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Cinnamic acids and derivatives
Sub Class
Cinnamic acid amides
Direct Parent
Cinnamic acid amides
Alternative Parents
Phenol esters / Styrenes / Phenoxy compounds / Dicarboxylic acids and derivatives / Secondary carboxylic acid amides / Carboxylic acid esters / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Carboxylic acid ester / Cinnamic acid amide / Dicarboxylic acid or derivatives / Hydrocarbon derivative / Monocyclic benzene moiety
show 10 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
GARHCDOTUULBOQ-PKNBQFBNSA-N
InChI
InChI=1S/C21H21NO5/c1-15(23)26-19-10-8-18(14-20(19)27-16(2)24)9-11-21(25)22-13-12-17-6-4-3-5-7-17/h3-11,14H,12-13H2,1-2H3,(H,22,25)/b11-9+
IUPAC Name
2-(acetyloxy)-5-[(1E)-2-[(2-phenylethyl)carbamoyl]eth-1-en-1-yl]phenyl acetate
SMILES
CC(=O)OC1=CC=C(\C=C\C(=O)NCCC2=CC=CC=C2)C=C1OC(C)=O

References

General References
Not Available
PubChem Compound
11957394
PubChem Substance
99445224
ChemSpider
10131649
ZINC
ZINC000016051983
PDBe Ligand
Y12
PDB Entries
2ew5

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 Solubility0.000717 mg/mLALOGPS
logP3.53ALOGPS
logP2.78Chemaxon
logS-5.7ALOGPS
pKa (Strongest Acidic)15.17Chemaxon
pKa (Strongest Basic)-0.39Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area81.7 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity101.41 m3·mol-1Chemaxon
Polarizability39.39 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9918
Blood Brain Barrier+0.9322
Caco-2 permeable+0.6298
P-glycoprotein substrateNon-substrate0.5226
P-glycoprotein inhibitor INon-inhibitor0.5375
P-glycoprotein inhibitor IINon-inhibitor0.6619
Renal organic cation transporterNon-inhibitor0.7822
CYP450 2C9 substrateNon-substrate0.7332
CYP450 2D6 substrateNon-substrate0.7589
CYP450 3A4 substrateSubstrate0.6608
CYP450 1A2 substrateNon-inhibitor0.5688
CYP450 2C9 inhibitorInhibitor0.5532
CYP450 2D6 inhibitorNon-inhibitor0.9006
CYP450 2C19 inhibitorInhibitor0.6248
CYP450 3A4 inhibitorNon-inhibitor0.6749
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5933
Ames testNon AMES toxic0.7095
CarcinogenicityNon-carcinogens0.8641
BiodegradationNot ready biodegradable0.5321
Rat acute toxicity2.0392 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9698
hERG inhibition (predictor II)Non-inhibitor0.6466
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/MSsplash10-066r-2219000000-56204a66626c3f7301fb
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ab9-3139000000-9f60015e18e4e06bee37
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0560-0695000000-b30ad53140c0bbefcf81
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9010000000-675bb4f40fb2b692debd
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004l-6960000000-77f194c25a21d0481bd3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9020000000-dadb4cb17cdb2aeb733a
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]-177.87492
predicted
DeepCCS 1.0 (2019)
[M+H]+180.23291
predicted
DeepCCS 1.0 (2019)
[M+Na]+187.21443
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Peptide deformylase
Kind
Protein
Organism
Helicobacter pylori
Pharmacological action
Unknown
General Function
Peptide deformylase activity
Specific Function
Removes the formyl group from the N-terminal Met of newly synthesized proteins. Requires at least a dipeptide for an efficient rate of reaction. N-terminal L-methionine is a prerequisite for activi...
Gene Name
def
Uniprot ID
Q672W7
Uniprot Name
Peptide deformylase
Molecular Weight
20038.335 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 21:34 / Updated at June 12, 2020 16:52