BIRD-PRD_001076: N-[(benzyloxy)carbonyl]-L-valyl-N~5~-[amino(iminio)methyl]-L-orni...

Basic information

• Entry: Database: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_001076
• Status: Status: REF ONLY
• Name: N-[(benzyloxy)carbonyl]-L-valyl-N~5~-[amino(iminio)methyl]-L-ornithyl-N-[(3R)-6-{[amino(iminio)methyl]amino}-1-fluoro-2-oxohexan-3-yl]-L-prolinamide

BIRD information

• Type: Oligopeptide / Inhibitor
• Downloads: Molecular definition / Chemical definition / Family definition

Synonyms

• MALT1 inhibitor (enzolifesciences.com)
• Z VRPR FMK (enzolifesciences.com)
• Z-Val-Arg-Pro-DL-Arg-FMK (enzolifesciences.com)
• z-VRPR-fmk (PDB)

Annotation

• Function: Inhibitor of Mucosa-associated lymphoid tissue lymphoma translocation protein 1, EC: 3.4.22.-EC: Inhibitor of Mucosa-associated lymphoid tissue lymphoma translocation protein 1, EC: 3.4.22.- / Info source: PubMed: 22158899
• Mechanism of action: The proteolytic activity of the paracaspase MALT1 is key to NF-kB and T cell activation. Z-VRPR-FMK is a selective MALT1 inhibitor of such proteolytic activity. / Info source: enzolifesciences.com

Family

VRPR-fluoromethyl ketone

N-[(benzyloxy)carbonyl]-L-valyl-N~5~-[amino(iminio)methyl]-L-ornithyl-N-[(3R)-6-{[amino(iminio)methyl]amino}-1-fluoro-2-oxohexan-3-yl]-L-prolinamide

Chemical information

Composition

Formula: C₃₁H₅₁FN₁₀O₆ / Formula weight: 678.798

• Others: Type: peptide-like

History

• External links: UniChem / ChemSpider / Wikipedia search / Google search

Details

SMILES

• ACDLabs 12.01: O=C(NC(C(=O)CF)CCCNC(=[NH2+])/N)C2N(C(=O)C(NC(=O)C(NC(=O)OCc1ccccc1)C(C)C)CCCNC(=[NH2+])\N)CCC2
• CACTVS 3.370: CC(C)[CH](NC(=O)OCc1ccccc1)C(=O)N[CH](CCCNC(N)=[NH2+])C(=O)N2CCC[CH]2C(=O)N[CH](CCCNC(N)=[NH2+])C(=O)CF
• OpenEye OEToolkits 1.7.6: CC(C)C(C(=O)NC(CCCNC(=[NH2+])N)C(=O)N1CCCC1C(=O)NC(CCCNC(=[NH2+])N)C(=O)CF)NC(=O)OCc2ccccc2

SMILES CANONICAL

• CACTVS 3.370: CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](CCCNC(N)=[NH2+])C(=O)N2CCC[C@H]2C(=O)N[C@@H](CCCNC(N)=[NH2+])C(=O)CF
• OpenEye OEToolkits 1.7.6: CC(C)[C@@H](C(=O)N[C@@H](CCCNC(=[NH2+])N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(=[NH2+])N)C(=O)CF)NC(=O)OCc2ccccc2

InChI

• InChI 1.03: InChI=1S/C31H49FN10O6/c1-19(2)25(41-31(47)48-18-20-9-4-3-5-10-20)27(45)40-22(12-7-15-38-30(35)36)28(46)42-16-8-13-23(42)26(44)39-21(24(43)17-32)11-6-14-37-29(33)34/h3-5,9-10,19,21-23,25H,6-8,11-18H2,1-2H3,(H,39,44)(H,40,45)(H,41,47)(H4,33,34,37)(H4,35,36,38)/p+2

InChIKey

• InChI 1.03: DYQKGOBRZWMAHV-UHFFFAOYSA-P

SYSTEMATIC NAME

• ACDLabs 12.01: N-[(benzyloxy)carbonyl]-L-valyl-N~5~-[amino(iminio)methyl]-L-ornithyl-N-[(3R)-6-{[amino(iminio)methyl]amino}-1-fluoro-2-oxohexan-3-yl]-L-prolinamide
• OpenEye OEToolkits 1.7.6: [[[(4S)-5-[(2S)-2-[[(3S)-6-[[azaniumylidene(azanyl)methyl]amino]-1-fluoranyl-2-oxidanylidene-hexan-3-yl]carbamoyl]pyrrolidin-1-yl]-4-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]-5-oxidanylidene-pentyl]amino]-azanyl-methylidene]azanium

PDB entries

Showing all 5 items

PDB-3uo8:
Crystal structure of the MALT1 paracaspase (P1 form)

PDB-3uoa:
Crystal structure of the MALT1 paracaspase (P21 form)

PDB-3v4l:
Mouse MALT1(caspase-IG3 domains) in complex with a irreversible peptidic inhibitor

PDB-3v4o:
Human MALT1 (caspase domain) in complex with an irreversible peptidic inhibitor

PDB-8v4x:
Structure of MALT1 in complex with an allosteric inhibitor