ChemFOnt: Showing chemical card for Tipranavir (CFc000009374)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:29 UTC

Chemfont ID

CFc000009374

Molecule Identification

Common Name

Tipranavir

Definition

Tipranavir is only found in individuals that have used or taken this drug. It is a sulfonamide-containing dyhydropyrone and a nonpeptidic protease inhibitor that targets the HIV protease. It is administered with ritonavir in combination therapy to treat HIV infections.Tipranavir inhibits the processing of the viral Gag and Gag-Pol polyproteins in HIV-1 infected cells, thus preventing formation of mature virions. Two mechanisms are suggested in regards to the potency of tipranavir: 1. Tipravanir may bind to the active site of the protease enzyme with fewer hydrogen bonds than peptidic protease inhibitors, which results in increased flexibility, allowing it to fit into the active site of the enzyme in viruses that have become resistance to other protease inhibitors. This also enables tipranavir to adjust to amino acid substitutions at the active site. 2. Tipranavir's strong hydrogen bonding interaction with the amide backbone of the protease active site Asp30 may lead to its activity against resistant viruses.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
TPV	HMDB
N-{3-[(1R)-1-[(2R)-6-hydroxy-4-oxo-2-(2-phenylethyl)-2-propyl-3,4-dihydro-2H-pyran-5-yl]propyl]phenyl}-5-(trifluoromethyl)pyridine-2-sulphonamide	Generator

Chemical Formula

C₃₁H₃₃F₃N₂O₅S

Average Molecular Weight

602.664

Monoisotopic Molecular Weight

602.206227481

IUPAC Name

N-{3-[(1R)-1-[(2R)-6-hydroxy-4-oxo-2-(2-phenylethyl)-2-propyl-3,4-dihydro-2H-pyran-5-yl]propyl]phenyl}-5-(trifluoromethyl)pyridine-2-sulfonamide

Traditional Name

aptivus

CAS Registry Number

174484-41-4

SMILES

CCC[C@@]1(CCC2=CC=CC=C2)CC(=O)C([C@H](CC)C2=CC(NS(=O)(=O)C3=NC=C(C=C3)C(F)(F)F)=CC=C2)=C(O)O1

InChI Identifier

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/h5-14,18,20,25,36,38H,3-4,15-17,19H2,1-2H3/t25-,30-/m1/s1

InChI Key

NZPXPXAGXYTROM-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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Linear diarylheptanoids

Alternative Parents

Substituents

Linear 1,7-diphenylheptane skeleton
Sulfanilide
Pyridine-2-sulfonamide
Phenylpropane
Dihydropyranone
Monocyclic benzene moiety
Organosulfonic acid amide
Benzenoid
Pyridine
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Vinylogous ester
Vinylogous acid
Heteroaromatic compound
Aminosulfonyl compound
Ketene acetal or derivatives
Ketone
Cyclic ketone
Oxacycle
Azacycle
Organoheterocyclic compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Alkyl fluoride
Alkyl halide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015067)
Membrane (HMDB: HMDB0015067)

Source

Exogenous

Exogenous (HMDB: HMDB0015067)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00021 g/L	ALOGPS
logP	5.71	ALOGPS
logP	7.81	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Acidic)	5.96	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.59 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	163.56 m³·mol⁻¹	ChemAxon
Polarizability	61.31 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0015067

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58539

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tipranavir

METLIN ID

Not Available

PubChem Compound

65027

PDB ID

Not Available

ChEBI ID

404696

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Tipranavir (CFc000009374)

MOL for CFc000009374 (Tipranavir)

3D MOL for CFc000009374 (Tipranavir)

3D SDF for CFc000009374 (Tipranavir)

3D-SDF for CFc000009374 (Tipranavir)

PDB for CFc000009374 (Tipranavir)

3D PDB for CFc000009374 (Tipranavir)

SMILES for CFc000009374 (Tipranavir)

INCHI for CFc000009374 (Tipranavir)

Structure for CFc000009374 (Tipranavir)

3D Structure for CFc000009374 (Tipranavir)