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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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
Classification Click here for help
Compound class Synthetic organic
Is prodrug? Yes
Active form lopinavir
Synonyms Click here for help
His-Leu-LPV | Histidine-Leucine-Lopinavir
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9680829
Reactome Reaction Reactome logo R-HSA-9697043
Other databases
GtoPdb PubChem SID 329968441
PubChem CID 124221655
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