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CHEBI:167663 - MI-1148

ChEBI IDCHEBI:167663
ChEBI NameMI-1148
Stars
DefinitionA tripeptide comprising of L-arginine, 3-methyl-L-valine and L-arginine joined in sequence by peptide linkages and in which the amino terminus is substituted by a [4-(carbamimidamidomethyl)phenyl]acetyl group and the carboxy terminus is substituted by a (4-carbamimidoylbenzyl)amino group. It is a highly potent inhibitor of furin endoprotease (Ki = 5.5 pM) that has anti-infectious activity.
Last Modified24 March 2021
SubmitterR. Stephan
DownloadsMolfile
FormulaC36H57N15O4
Net Charge0
Average Mass763.953
Monoisotopic Mass763.47180
SMILESCC(C)(C)[C@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)Cc1ccc(CNC(=N)N)cc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)NCc1ccc(C(=N)N)cc1
InChIInChI=1S/C36H57N15O4/c1-36(2,3)28(32(55)50-25(6-4-16-45-33(39)40)30(53)47-19-23-12-14-24(15-13-23)29(37)38)51-31(54)26(7-5-17-46-34(41)42)49-27(52)18-21-8-10-22(11-9-21)20-48-35(43)44/h8-15,25-26,28H,4-7,16-20H2,1-3H3,(H3,37,38)(H,47,53)(H,49,52)(H,50,55)(H,51,54)(H4,39,40,45)(H4,41,42,46)(H4,43,44,48)/t25-,26-,28+/m0/s1
InChIKeyHXVPWVPTVOOCMV-UNCTUWKVSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
EC 3.4.21.75 (furin) inhibitor  An EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of furin (EC 3.4.21.75).
antiviral agent  A substance that destroys or inhibits replication of viruses.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
peptidomimetic  A small protein-like chain designed to mimic a peptide.
ChEBI Ontology
Outgoing Relation(s)
MI-1148 (CHEBI:167663) has functional parent L-arginine (CHEBI:16467)
MI-1148 (CHEBI:167663) has role antibacterial agent (CHEBI:33282)
MI-1148 (CHEBI:167663) has role antiviral agent (CHEBI:22587)
MI-1148 (CHEBI:167663) has role EC 3.4.21.75 (furin) inhibitor (CHEBI:156297)
MI-1148 (CHEBI:167663) has role peptidomimetic (CHEBI:63175)
MI-1148 (CHEBI:167663) is a tripeptide (CHEBI:47923)
IUPAC Name 
N2-{[4-(carbamimidamidomethyl)phenyl]acetyl}-L-arginyl-3-methyl-L-valyl-N-(4-carbamimidoylbenzyl)-L-argininamide
Synonyms  Source
MI 1148ChEBI
MI1148ChEBI
N2-{[4-(carbamimidamidomethyl)phenyl]acetyl}-L-arginyl-3-methyl-L-valyl-N-[(4-carbamimidoylphenyl)methyl]-L-argininamideIUPAC
(2S)-5-carbamimidamido-2-{[(2S)-2-{[(2S)-5-carbamimidamido-2-{2-[4-(carbamimidamidomethyl)phenyl]acetamido}pentanoyl]amino}-3,3-dimethylbutanoyl]amino}-N-(4-carbamimidoylbenzyl)pentanamideIUPAC
4-(guanidinomethyl)phenylacetyl-Arg-Tle-Arg-4-amidinobenzylamideChEBI
4-guanidinomethyl-phenylacteyl-Arg-Tle-Arg-4-amidinobenzylamideChEBI
Manual XrefsDatabases
35033268ChemSpider
Citations