BIRD-PRD_000976: N-acetyl-L-valyl-L-alpha-glutamyl-N-[(2S)-1-carboxy-3-oxopropan-2...

Basic information

• Entry: Database: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000976
• Status: Status: REF ONLY
• Name: N-acetyl-L-valyl-L-alpha-glutamyl-N-[(2S)-1-carboxy-3-oxopropan-2-yl]-L-isoleucinamide

BIRD information

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

Family

aspartate aldehyde containing tetrapeptide inhibitors

N-acetyl-L-leucyl-L-alpha-aspartyl-L-alpha-glutamyl-L-seryl-L-aspartic aldehyde / N-acetyl-L-tryptophyl-L-alpha-glutamyl-N-[(1R)-2-carboxy-1-formylethyl]-3-(1H-imidazol-3-ium-4-yl)-L-alaninamide / N-acetyl-L-alpha-aspartyl-L-asparaginyl-N-[(1R)-2-carboxy-1-formylethyl]-L-leucinamide / AC-DQMD-CHO / INHIBITOR AC-ESMD-CHO / N-acetyl-L-isoleucyl-L-alpha-glutamyl-N-[(1S)-2-carboxy-1-formylethyl]-L-prolinamide / N-(2-oxoethyl)-L-isoleucyl-L-alpha-glutamyl-N-[(1R)-2-carboxy-1-formylethyl]-L-threoninamide / N-acetyl-L-valyl-L-alpha-glutamyl-N-[(2S)-1-carboxy-3-oxopropan-2-yl]-L-isoleucinamide

Chemical information

Composition

Formula: C₂₂H₃₆N₄O₉ / Formula weight: 500.543

• Others: Type: peptide-like

History

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

Details

SMILES

• ACDLabs 12.01: O=C(NC(C=O)CC(=O)O)C(NC(=O)C(NC(=O)C(NC(=O)C)C(C)C)CCC(=O)O)C(C)CC
• CACTVS 3.370: CC[CH](C)[CH](NC(=O)[CH](CCC(O)=O)NC(=O)[CH](NC(C)=O)C(C)C)C(=O)N[CH](CC(O)=O)C=O
• OpenEye OEToolkits 1.7.6: CCC(C)C(C(=O)NC(CC(=O)O)C=O)NC(=O)C(CCC(=O)O)NC(=O)C(C(C)C)NC(=O)C

SMILES CANONICAL

• CACTVS 3.370: CC[C@H](C)[C@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(C)=O)C(C)C)C(=O)N[C@@H](CC(O)=O)C=O
• OpenEye OEToolkits 1.7.6: CC[C@H](C)[C@@H](C(=O)N[C@@H](CC(=O)O)C=O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C(C)C)NC(=O)C

InChI

• InChI 1.03: InChI=1S/C22H36N4O9/c1-6-12(4)19(22(35)24-14(10-27)9-17(31)32)26-20(33)15(7-8-16(29)30)25-21(34)18(11(2)3)23-13(5)28/h10-12,14-15,18-19H,6-9H2,1-5H3,(H,23,28)(H,24,35)(H,25,34)(H,26,33)(H,29,30)(H,31,32)/t12-,14-,15+,18-,19-/m0/s1

InChIKey

• InChI 1.03: KYUFGGNCJRWMDN-DYOXLCOFSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: N-acetyl-L-valyl-L-alpha-glutamyl-N-[(2S)-1-carboxy-3-oxopropan-2-yl]-L-isoleucinamide
• OpenEye OEToolkits 1.7.6: (4S)-4-[[(2S)-2-acetamido-3-methyl-butanoyl]amino]-5-[[(2S,3S)-3-methyl-1-[[(2S)-4-oxidanyl-1,4-bis(oxidanylidene)butan-2-yl]amino]-1-oxidanylidene-pentan-2-yl]amino]-5-oxidanylidene-pentanoic acid

PDB entries

Showing all 3 items

PDB-3od5:
Crystal structure of active caspase-6 bound with Ac-VEID-CHO

PDB-3s70:
Crystal structure of active caspase-6 bound with Ac-VEID-CHO solved by As-SAD

PDB-4zvq:
Caspase-7 Variant 2 (V2) with reprogrammed substrate specificity due to Y230V/W232M/Q276C substitutions bound to VEID inhibitor.