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CHEBI:46238 - U100313

ChEBI IDCHEBI:46238
ChEBI NameU100313
Stars
DefinitionA pyranone that is 4-hydroxy-3-methyl-2H-pyran-2-one in which two of the hydrogens of the methyl group are replaced by a cycloprop-2-en-1-yl group and a 3-{[N-(tert-butoxycarbonyl)-β-alanyl]amino}phenyl group (S-configuration) and in which the hydrogen at position 6 is replaced by a 1-phenylbutan-2-yl group (R-configuration).
Last Modified11 May 2016
DownloadsMolfile
FormulaC33H38N2O6
Net Charge0
Average Mass558.675
Monoisotopic Mass558.27299
SMILES[H][C@](c1cccc(NC(=O)CCNC(=O)OC(C)(C)C)c1)(c1c(O)cc([C@H](CC)Cc2ccccc2)oc1=O)C1C=C1
InChIInChI=1S/C33H38N2O6/c1-5-22(18-21-10-7-6-8-11-21)27-20-26(36)30(31(38)40-27)29(23-14-15-23)24-12-9-13-25(19-24)35-28(37)16-17-34-32(39)41-33(2,3)4/h6-15,19-20,22-23,29,36H,5,16-18H2,1-4H3,(H,34,39)(H,35,37)/t22-,29+/m1/s1
InChIKeyOORLDLMDGJZAFM-MNNSJKJDSA-N
Roles Classification
Biological Role:
HIV protease inhibitor  An inhibitor of HIV protease, an enzyme required for production of proteins needed for viral assembly.
ChEBI Ontology
Outgoing Relation(s)
U100313 (CHEBI:46238) has role HIV protease inhibitor (CHEBI:35660)
U100313 (CHEBI:46238) is a 2-pyranones (CHEBI:75885)
U100313 (CHEBI:46238) is a anilide (CHEBI:13248)
U100313 (CHEBI:46238) is a carbamate ester (CHEBI:23003)
U100313 (CHEBI:46238) is a cyclopropenes (CHEBI:51455)
U100313 (CHEBI:46238) is a monocarboxylic acid amide (CHEBI:29347)
IUPAC Name 
tert-butyl [3-({3-[(S)-cycloprop-2-en-1-yl{4-hydroxy-2-oxo-6-[(2R)-1-phenylbutan-2-yl]-2H-pyran-3-yl}methyl]phenyl}amino)-3-oxopropyl]carbamate
Synonym  Source
tert-butyl [3-({3-[(S)-{6-[(1R)-1-benzylpropyl]-4-hydroxy-2-oxo-2H-pyran-3-yl}(cycloprop-2-en-1-yl)methyl]phenyl}amino)-3-oxopropyl]carbamateIUPAC
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Citations