CHEBI:167663 - MI-1148

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name MI-1148
ChEBI ID CHEBI:167663
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter R. Stephan
Supplier Information
Download Molfile XML SDF
Formula C36H57N15O4
Net Charge 0
Average Mass 763.953
Monoisotopic Mass 763.47180
InChI InChI=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
InChIKey HXVPWVPTVOOCMV-UNCTUWKVSA-N
SMILES CC(C)(C)[C@H](NC(=O)[C@H](CCCNC(N)=N)NC(=O)CC1=CC=C(CNC(N)=N)C=C1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC1=CC=C(C=C1)C(N)=N
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): peptidomimetic
A small protein-like chain designed to mimic a peptide.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
(2S)-5-carbamimidamido-2-{[(2S)-2-{[(2S)-5-carbamimidamido-2-{2-[4-(carbamimidamidomethyl)phenyl]acetamido}pentanoyl]amino}-3,3-dimethylbutanoyl]amino}-N-(4-carbamimidoylbenzyl)pentanamide IUPAC
4-(guanidinomethyl)phenylacetyl-Arg-Tle-Arg-4-amidinobenzylamide ChEBI
4-guanidinomethyl-Phac-Arg-Tle-Arg-4-amba ChEBI
4-guanidinomethyl-phenylacteyl-Arg-Tle-Arg-4-amidinobenzylamide ChEBI
MI 1148 ChEBI
MI1148 ChEBI
N2-{[4-(carbamimidamidomethyl)phenyl]acetyl}-L-arginyl-3-methyl-L-valyl-N-[(4-carbamimidoylphenyl)methyl]-L-argininamide IUPAC
Manual Xref Database
35033268 ChemSpider
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Citations Waiting for Citations Types Sources
21757345 PubMed citation Europe PMC
22539349 PubMed citation Europe PMC
25974265 PubMed citation SUBMITTER
29059503 PubMed citation Europe PMC
Last Modified
24 March 2021