etravirine (CHEM044233)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:54:16 UTC
Update Date2016-11-09 01:23:05 UTC
Accession NumberCHEM044233
Identification
Common Nameetravirine
ClassSmall Molecule
DescriptionAn aminopyrimidine that consists of 2,6-diaminopyrimidine bearing a bromo substituent at position 5, a 4-cyano-2,6-dimethylphenoxy substituent at position 4 and having a 4-cyanophenyl substituent attached to the 2-amino group. NNRTI of HIV-1, binds directly to RT and blocks RNA-dependent and DNA-dependent DNA polymerase activities
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
IntelenceKegg
TMC-125MeSH
TMC 125MeSH
TMC125 CPDMeSH
4-((6-Amino-5-bromo-2-((4-cyanophenyl)amino)-4-pyrimidinyl)oxy)-3,5-dimethyl-benzonitrileMeSH
Chemical FormulaC20H15BrN6O
Average Molecular Mass435.277 g/mol
Monoisotopic Mass434.049 g/mol
CAS Registry Number269055-15-4
IUPAC Name4-({6-amino-5-bromo-2-[(4-cyanophenyl)amino]pyrimidin-4-yl}oxy)-3,5-dimethylbenzonitrile
Traditional Nameetravirine
SMILESCC1=CC(=CC(C)=C1OC1=C(Br)C(N)=NC(NC2=CC=C(C=C2)C#N)=N1)C#N
InChI IdentifierInChI=1S/C20H15BrN6O/c1-11-7-14(10-23)8-12(2)17(11)28-19-16(21)18(24)26-20(27-19)25-15-5-3-13(9-22)4-6-15/h3-8H,1-2H3,(H3,24,25,26,27)
InChI KeyPYGWGZALEOIKDF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentDiarylethers
Alternative Parents
Substituents
  • Diaryl ether
  • Phenoxy compound
  • M-xylene
  • Xylene
  • Aniline or substituted anilines
  • Benzonitrile
  • Phenol ether
  • Aminopyrimidine
  • Halopyrimidine
  • Aryl bromide
  • Aryl halide
  • Monocyclic benzene moiety
  • Imidolactam
  • Benzenoid
  • Pyrimidine
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Carbonitrile
  • Nitrile
  • Primary amine
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organohalogen compound
  • Organobromide
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP3.67ALOGPS
logP5.54ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)12.49ChemAxon
pKa (Strongest Basic)4.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area120.64 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity111.87 m³·mol⁻¹ChemAxon
Polarizability41.09 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-0911200000-26b25d818a5bc993076dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udj-0910000000-f7b2a59bcc1e1195bf1fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udj-0910000000-f7b2a59bcc1e1195bf1fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0101900000-33e354fd9e3dbad9ddb6Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4r-0100900000-da01bbb7f5f5d708476eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0200900000-6a47ddb2c0af0c13958bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-0920700000-204b4b935ade39e75488Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9210000000-c33a116eb4da6922eb33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0200900000-e41efbdc46d53beb49d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0910200000-bfe072d13f41d5e47c4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-029y-1920000000-46573f23be5d4f069730Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB06414
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEtravirine
Chemspider IDNot Available
ChEBI ID63589
PubChem Compound ID193962
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21114458
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21142266
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21173188
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21189339
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21383098
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21464253
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21557669
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21600016
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21637112
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21881478
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22011983
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22089378
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22190606
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=25017682