amprenavir   Click here for help

GtoPdb Ligand ID: 12681

Synonyms: Agenerase® | AMV | Prozei® | VX-478 | VX478
Approved drug PDB Ligand
amprenavir is an approved drug (FDA (1999))
Compound class: Synthetic organic
Comment: Amprenavir 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 9
Hydrogen bond donors 3
Rotatable bonds 13
Topological polar surface area 139.57
Molecular weight 505.63
XLogP 1.15
No. Lipinski's rules broken 2
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 CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CCOC2)O)S(=O)(=O)C3=CC=C(C=C3)N
Isomeric SMILES CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CCOC2)O)S(=O)(=O)C3=CC=C(C=C3)N
InChI InChI=1S/C25H35N3O6S/c1-18(2)15-28(35(31,32)22-10-8-20(26)9-11-22)16-24(29)23(14-19-6-4-3-5-7-19)27-25(30)34-21-12-13-33-17-21/h3-11,18,21,23-24,29H,12-17,26H2,1-2H3,(H,27,30)/t21-,23-,24+/m0/s1
InChI Key YMARZQAQMVYCKC-OEMFJLHTSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1999))
Withdrawn drug? Yes
Prodrug fosamprenavir
IUPAC Name Click here for help
[(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
International Nonproprietary Names Click here for help
INN number INN
7751 amprenavir
Synonyms Click here for help
Agenerase® | AMV | Prozei® | VX-478 | VX478
Database Links Click here for help
BindingDB Ligand 50215393
ChEBI CHEBI:40050
ChEMBL Ligand CHEMBL116
DrugBank Ligand DB00701
GtoPdb PubChem SID 483123229
PubChem CID 65016
RCSB PDB Ligand 478
Search Google for chemical match using the InChIKey YMARZQAQMVYCKC-OEMFJLHTSA-N
Search Google for chemicals with the same backbone YMARZQAQMVYCKC
Search PubMed clinical trials amprenavir
Search PubMed titles amprenavir
Search PubMed titles/abstracts amprenavir
UniChem Compound Search for chemical match using the InChIKey YMARZQAQMVYCKC-OEMFJLHTSA-N
UniChem Connectivity Search for chemical match using the InChIKey YMARZQAQMVYCKC-OEMFJLHTSA-N