elunonavir   Click here for help

GtoPdb Ligand ID: 11667

Compound class: Synthetic organic
Comment: The chemical structure for elunonavir was obtained from WHO Proposed list 125. The IUPAC>SMILES conversion maps to PubChem CID 135301900. Via SureChEMBL we can trace this compound to a Gilead Sciences patent that claims antiviral compounds for the treatment of HIV [1]. From the patent it would appear that elunonavir is an HIV protease inhibitor.
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 18
Hydrogen bond donors 5
Rotatable bonds 27
Topological polar surface area 217.64
Molecular weight 1155.44
XLogP 8.47
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 COC(=O)N[C@@H](C(C(F)(F)F)(C)C)C(=O)N[C@H]([C@H](CN(Cc1c(F)cc(cc1F)c1ccn(n1)C(F)F)NC(=O)[C@H](C(C(F)(F)F)(C)C)NC(=O)OC)O)Cc1ccc(cc1)C#Cc1cnc(nc1)N1CC2CCC(C1)N2C1COC1
Isomeric SMILES CC(C)([C@@H](C(=O)N[C@@H](Cc1ccc(cc1)C#Cc1cnc(nc1)N1CC2CCC(C1)N2C1COC1)[C@H](CN(Cc1c(cc(cc1F)c1nn(cc1)C(F)F)F)NC(=O)[C@H](C(C)(C)C(F)(F)F)NC(=O)OC)O)NC(=O)OC)C(F)(F)F
InChI InChI=1S/C52H59F10N11O8/c1-49(2,51(57,58)59)41(66-47(77)79-5)43(75)65-39(17-29-10-7-28(8-11-29)9-12-30-20-63-46(64-21-30)70-22-32-13-14-33(23-70)73(32)34-26-81-27-34)40(74)25-71(69-44(76)42(67-48(78)80-6)50(3,4)52(60,61)62)24-35-36(53)18-31(19-37(35)54)38-15-16-72(68-38)45(55)56/h7-8,10-11,15-16,18-21,32-34,39-42,45,74H,13-14,17,22-27H2,1-6H3,(H,65,75)(H,66,77)(H,67,78)(H,69,76)/t32?,33?,39-,40-,41+,42+/m0/s1
InChI Key ZTSLYWLHCOINNI-FTEFBJIISA-N
References
1. Bacon EM, Chin E, Cottell JJ, Katana AA, Kato D, Link JO, Shapiro N, Martin TAT, Yang Z-Y. (2020)
HIV inhibitor compounds.
Patent number: US10752636B2. Assignee: Gilead Sciences Inc. Priority date: 06/02/2017. Publication date: 25/08/2020.