N-[(1R,2R)-1,3-Dihydroxy-1-(4-nitrophenyl)-2-propanyl]acetamide

Identification

Generic Name
N-[(1R,2R)-1,3-Dihydroxy-1-(4-nitrophenyl)-2-propanyl]acetamide
DrugBank Accession Number
DB02608
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 254.2393
Monoisotopic: 254.090271568
Chemical Formula
C11H14N2O5
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UChloramphenicol 3-O phosphotransferaseNot AvailableStreptomyces venezuelae (strain ATCC 10712 / CBS 650.69 / DSM 40230 / JCM 4526 / NBRC 13096 / PD 04745)
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
Adverseeffects
Improve decision support & research outcomes
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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 nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Nitrobenzenes
Direct Parent
Nitrobenzenes
Alternative Parents
Nitroaromatic compounds / Acetamides / Secondary carboxylic acid amides / Secondary alcohols / Propargyl-type 1,3-dipolar organic compounds / Organic oxoazanium compounds / Primary alcohols / Organopnictogen compounds / Organonitrogen compounds / Organic zwitterions
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Substituents
Acetamide / Alcohol / Allyl-type 1,3-dipolar organic compound / Aromatic alcohol / Aromatic homomonocyclic compound / C-nitro compound / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Hydrocarbon derivative
show 16 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
4423-58-9
InChI Key
PIVQDUYOEIAFDM-GHMZBOCLSA-N
InChI
InChI=1S/C11H14N2O5/c1-7(15)12-10(6-14)11(16)8-2-4-9(5-3-8)13(17)18/h2-5,10-11,14,16H,6H2,1H3,(H,12,15)/t10-,11-/m1/s1
IUPAC Name
N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
SMILES
[H]N([C@H](CO)[C@H](O)C1=CC=C(C=C1)[N+]([O-])=O)C(C)=O

References

General References
Not Available
PubChem Compound
247978
PubChem Substance
46507211
ChemSpider
217100
ZINC
ZINC000000174039
PDBe Ligand
CLC
PDB Entries
1grr

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 Solubility2.97 mg/mLALOGPS
logP0.13ALOGPS
logP-0.4ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)12.56ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area112.7 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity62.22 m3·mol-1ChemAxon
Polarizability24.23 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8312
Blood Brain Barrier+0.8221
Caco-2 permeable+0.5665
P-glycoprotein substrateNon-substrate0.6144
P-glycoprotein inhibitor INon-inhibitor0.9169
P-glycoprotein inhibitor IINon-inhibitor0.8614
Renal organic cation transporterNon-inhibitor0.9509
CYP450 2C9 substrateNon-substrate0.7523
CYP450 2D6 substrateNon-substrate0.8627
CYP450 3A4 substrateNon-substrate0.5884
CYP450 1A2 substrateNon-inhibitor0.899
CYP450 2C9 inhibitorNon-inhibitor0.7972
CYP450 2D6 inhibitorNon-inhibitor0.9338
CYP450 2C19 inhibitorInhibitor0.6362
CYP450 3A4 inhibitorNon-inhibitor0.8627
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9066
Ames testNon AMES toxic0.6399
CarcinogenicityNon-carcinogens0.6448
BiodegradationReady biodegradable0.7559
Rat acute toxicity2.1882 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9488
hERG inhibition (predictor II)Non-inhibitor0.8711
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

Targets

Drugtargets2
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Kind
Protein
Organism
Streptomyces venezuelae (strain ATCC 10712 / CBS 650.69 / DSM 40230 / JCM 4526 / NBRC 13096 / PD 04745)
Pharmacological action
Unknown
General Function
Kinase activity
Specific Function
Inactivates chloramphenicol by catalyzing the transfer of the gamma-phosphate of ATP to the antibiotic's C-3' hydroxyl group.
Gene Name
Not Available
Uniprot ID
Q56148
Uniprot Name
Chloramphenicol 3-O phosphotransferase
Molecular Weight
18816.255 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at August 01, 2020 13:44