Tipranavir (CHEM019863)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:35:40 UTC
Update Date2016-11-09 01:16:05 UTC
Accession NumberCHEM019863
Identification
Common NameTipranavir
ClassSmall Molecule
DescriptionTipranavir is a sulfonamide-containing dyhydropyrone and a nonpeptidic protease inhibitor that targets the HIV protease. Tipranavir and ritonavir are coadministered to treat HIV.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3'-((1R)-1-((6R)-5,6-Dihydro-4-hydroxy-2-oxo-6-phenethyl-6-propyl-2H-pyran-3-yl)propyl)-5-(trifluoromethyl)-2-pyridinesulfonanilideChEBI
AptivusKegg
3'-((1R)-1-((6R)-5,6-Dihydro-4-hydroxy-2-oxo-6-phenethyl-6-propyl-2H-pyran-3-yl)propyl)-5-(trifluoromethyl)-2-pyridinesulphonanilideGenerator
Tipranavir, (R-(r*,r*))-isomerMeSH
Tipranavir, (S-(r*,r*))-isomerMeSH
Tipranavir, (S-(r*,s*))-isomerMeSH
Chemical FormulaC31H33F3N2O5S
Average Molecular Mass602.664 g/mol
Monoisotopic Mass602.206 g/mol
CAS Registry Number174484-41-4
IUPAC NameN-{3-[(1R)-1-[(6R)-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-5,6-dihydro-2H-pyran-3-yl]propyl]phenyl}-5-(trifluoromethyl)pyridine-2-sulfonamide
Traditional Nametipranavir
SMILES[H][C@@](CC)(C1=CC(NS(=O)(=O)C2=NC=C(C=C2)C(F)(F)F)=CC=C1)C1=C(O)C[C@@](CCC)(CCC2=CC=CC=C2)OC1=O
InChI IdentifierInChI=1S/C31H33F3N2O5S/c1-3-16-30(17-15-21-9-6-5-7-10-21)19-26(37)28(29(38)41-30)25(4-2)22-11-8-12-24(18-22)36-42(39,40)27-14-13-23(20-35-27)31(32,33)34/h5-14,18,20,25,36-37H,3-4,15-17,19H2,1-2H3/t25-,30-/m1/s1
InChI KeySUJUHGSWHZTSEU-FYBSXPHGSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDiarylheptanoids
Sub ClassLinear diarylheptanoids
Direct ParentLinear diarylheptanoids
Alternative Parents
Substituents
  • Linear 1,7-diphenylheptane skeleton
  • Pyridine-2-sulfonamide
  • Sulfanilide
  • Phenylpropane
  • Dihydropyranone
  • Monocyclic benzene moiety
  • Pyran
  • Pyridine
  • Organosulfonic acid amide
  • Benzenoid
  • Heteroaromatic compound
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Vinylogous acid
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Enol
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Azacycle
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Alkyl fluoride
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Organic oxide
  • Alkyl halide
  • 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 Solubility0.0002 g/LALOGPS
logP6.29ALOGPS
logP7.14ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)5.92ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.59 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity154.57 m³·mol⁻¹ChemAxon
Polarizability60.87 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ugl-4518749000-d091860c6bd16b05efe5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-2912000000-b072642a58ca83226a8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9701010000-ca1e6c1b1e2713a691c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0822069000-8e905312861733573a7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0391121000-48726f30b7ab1a53041eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000j-5920000000-84b97d9d9eef7c125e6aSpectrum
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 IDDB00932
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 LinkTipranavir
Chemspider IDNot Available
ChEBI ID63628
PubChem Compound IDNot Available
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=17620375
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20368406
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21041916
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21571982
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21576452
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21825300
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21871444
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22007990
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22096044
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22258921
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=25017682