tipranavir   Click here for help

GtoPdb Ligand ID: 12685

Synonyms: Aptivus® | PNU-140690 | TPV | U-140690
Approved drug PDB Ligand
tipranavir is an approved drug (FDA & EMA (2005))
Compound class: Synthetic organic
Comment: Tipranavir is an anti-HIV-1 agent. It inhibits the viral protease.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 12
Topological polar surface area 113.44
Molecular weight 602.67
XLogP 5.13
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCC[C@@]1(CCC2=CC=CC=C2)CC(=C([C@H](CC)C3=CC=CC(=C3)NS(=O)(=O)C4=CC=C(C=N4)C(F)(F)F)C(=O)O1)O
Isomeric SMILES CCC[C@]1(CC(=C(C(=O)O1)[C@H](CC)C2=CC(=CC=C2)NS(=O)(=O)C3=NC=C(C=C3)C(F)(F)F)O)CCC4=CC=CC=C4
InChI InChI=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 Key SUJUHGSWHZTSEU-FYBSXPHGSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA & EMA (2005))
IUPAC Name Click here for help
N-[3-[(1R)-1-[(2R)-4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3H-pyran-5-yl]propyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide
International Nonproprietary Names Click here for help
INN number INN
7774 tipranavir
Synonyms Click here for help
Aptivus® | PNU-140690 | TPV | U-140690
Database Links Click here for help
BindingDB Ligand 50479982
CAS Registry No. 174484-41-4 (source: WHO INN record)
ChEBI CHEBI:63628
ChEMBL Ligand CHEMBL222559
DrugBank Ligand DB00932
GtoPdb PubChem SID 483123233
PubChem CID 54682461
RCSB PDB Ligand TPV
Search Google for chemical match using the InChIKey SUJUHGSWHZTSEU-FYBSXPHGSA-N
Search Google for chemicals with the same backbone SUJUHGSWHZTSEU
Search PubMed clinical trials tipranavir
Search PubMed titles tipranavir
Search PubMed titles/abstracts tipranavir
UniChem Compound Search for chemical match using the InChIKey SUJUHGSWHZTSEU-FYBSXPHGSA-N
UniChem Connectivity Search for chemical match using the InChIKey SUJUHGSWHZTSEU-FYBSXPHGSA-N