His-Leu-lopinavir   Click here for help

GtoPdb Ligand ID: 9502

Synonyms: His-Leu-LPV | Histidine-Leucine-Lopinavir
Compound class: Synthetic organic
Comment: A histidine based dipeptide prodrug of lopinavir (PubChem CID 92727). Lopinavir is an HIV protease inhibitor used in a fixed-dose combination with ritonavir. It is also an inhibitor of cytochrome P450 CYP3A.
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 13
Hydrogen bond donors 6
Rotatable bonds 29
Topological polar surface area 209.87
Molecular weight 906.54
XLogP 6.03
No. Lipinski's rules broken 4

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC(CC(CC(=O)OC(C(Cc1ccccc1)NC(=O)COc1c(C)cccc1C)CC(NC(=O)C(N1CCCNC1=O)C(C)C)Cc1ccccc1)NC(=O)CC(Cc1c[nH]cn1)N)C
Isomeric SMILES CC(CC(CC(=O)O[C@H]([C@H](Cc1ccccc1)NC(=O)COc1c(C)cccc1C)C[C@@H](NC(=O)[C@@H](N1CCCNC1=O)C(C)C)Cc1ccccc1)NC(=O)CC(Cc1c[nH]cn1)N)C
InChI InChI=1S/C51H70N8O7/c1-33(2)23-40(56-45(60)27-39(52)26-42-30-53-32-55-42)29-47(62)66-44(43(25-38-19-11-8-12-20-38)58-46(61)31-65-49-35(5)15-13-16-36(49)6)28-41(24-37-17-9-7-10-18-37)57-50(63)48(34(3)4)59-22-14-21-54-51(59)64/h7-13,15-20,30,32-34,39-41,43-44,48H,14,21-29,31,52H2,1-6H3,(H,53,55)(H,54,64)(H,56,60)(H,57,63)(H,58,61)/t39?,40?,41-,43-,44-,48-/m0/s1
InChI Key CNRARJITWNMDCM-XGZCXRAPSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Mandal A, Pal D, Mitra AK. (2016)
Circumvention of P-gp and MRP2 mediated efflux of lopinavir by a histidine based dipeptide prodrug.
Int J Pharm, 512 (1): 49-60. [PMID:27543355]