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CHEBI:74858 - GCB

ChEBI IDCHEBI:74858
ChEBI NameGCB
Stars
DefinitionAn organic disulfide that is L-685,458 in which the C-terminal amide group is coupled to a biotin moiety via a long linker containing the disulfide group.
Last Modified5 March 2014
SubmitterMargaret Duesbury
DownloadsMolfile
FormulaC82H130N10O20S3
Net Charge0
Average Mass1672.193
Monoisotopic Mass1670.86250
SMILES[H][C@]12CS[C@@H](CCCCC(=O)NCCSSCCC(=O)NCCCOCCOCCOCCCNC(=O)COCCOCCOCC(=O)NCCCOCCOCCOCCCNC(=O)[C@H](Cc3ccccc3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc3ccccc3)C[C@@H](O)[C@H](Cc3ccccc3)NC(=O)OC(C)(C)C)[C@@]1([H])NC(=O)N2
InChIInChI=1S/C82H130N10O20S3/c1-61(2)53-67(88-77(98)65(54-62-21-9-6-10-22-62)57-70(93)66(55-63-23-11-7-12-24-63)91-81(102)112-82(3,4)5)79(100)89-68(56-64-25-13-8-14-26-64)78(99)87-33-20-38-106-42-46-108-45-41-105-37-19-32-85-75(97)59-111-50-48-109-47-49-110-58-74(96)84-31-18-36-104-40-44-107-43-39-103-35-17-30-83-73(95)29-51-114-115-52-34-86-72(94)28-16-15-27-71-76-69(60-113-71)90-80(101)92-76/h6-14,21-26,61,65-71,76,93H,15-20,27-60H2,1-5H3,(H,83,95)(H,84,96)(H,85,97)(H,86,94)(H,87,99)(H,88,98)(H,89,100)(H,91,102)(H2,90,92,101)/t65-,66+,67+,68+,69+,70-,71+,76+/m1/s1
InChIKeyIMMOTHDSNAXMDK-NLYMJQDSSA-N
Roles Classification
Biological Role:
EC 3.4.23.46 (memapsin 2) inhibitor  An EC 3.4.23.* (aspartic endopeptidase) inhibitor that interferes with the activity of memapsin 2 (EC 3.4.23.46).
ChEBI Ontology
Outgoing Relation(s)
GCB (CHEBI:74858) has functional parent biotin (CHEBI:15956)
GCB (CHEBI:74858) has functional parent L-685,458 (CHEBI:74921)
GCB (CHEBI:74858) has role EC 3.4.23.46 (memapsin 2) inhibitor (CHEBI:74925)
GCB (CHEBI:74858) is a carbamate ester (CHEBI:23003)
GCB (CHEBI:74858) is a monocarboxylic acid amide (CHEBI:29347)
GCB (CHEBI:74858) is a organic disulfide (CHEBI:35489)
GCB (CHEBI:74858) is a polyether (CHEBI:46774)
GCB (CHEBI:74858) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
N-{(2R,4R,5S)-2-benzyl-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenylhexanoyl}-L-leucyl-N-{15,25,41,49-tetraoxo-53-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-4,7,10,17,20,23,30,33,36-nonaoxa-44,45-dithia-14,26,40,48-tetraazatripentacont-1-yl}-L-phenylalaninamide
Citations