BIRD-PRD_000336: Cbz-Leu-Glu-Thr-AAsp-CHCH-CON-tetrahydroquinoline

Basic information

• Entry: Database: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000336
• Status: Status: REF ONLY
• Name: Cbz-Leu-Glu-Thr-AAsp-CHCH-CON-tetrahydroquinoline

BIRD information

• Type: Peptide-like / Inhibitor
• Downloads: Molecular definition / Chemical definition / Family definition

Annotation

• Function: aza-peptide Michael acceptor inhibitor of CASPASE-8, EC: 3.4.22.61EC: aza-peptide Michael acceptor inhibitor of CASPASE-8, EC: 3.4.22.61 / Info source: PubMed: 16970398

External info

• ChemSpider: 7828114
• PubChem: 9549192

Family

AZA-PEPTIDE MICHAEL ACCEPTOR INHIBITORS

(5S,8R,11S)-8-(2-carboxyethyl)-5-(carboxymethyl)-14-(4-ethoxy-4-oxobutanoyl)-11-(1-methylethyl)-3,6,9,12-tetraoxo-1-phe nyl-2-oxa-4,7,10,13,14-pentaazahexadecan-16-oic acid / Cbz-Asp-Glu-Val-AAsp-CHCH-CON(CH3)CH2Ph / Cbz-Leu-Glu-Thr-AAsp-CHCH-CON-tetrahydroquinoline / (5S, 8R, 11S)-14-[4-(BENZYLOXY)-4-OXOBUTANOYL]-8-(2-CARBOXYETHYL)-5-(CARBOXYMETHYL)-11- (1-METHYLETHYL)-3,6,9,12-TETRAOXO-1-PHENYL-2-OXA-4,7,10,13,14-PENTAAZAHEXADECAN-16-OIC ACID

Chemical information

Composition

Formula: C₃₈H₅₀N₆O₁₂ / Formula weight: 782.837

• Others: Type: peptide-like

History

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

Details

SMILES

• ACDLabs 12.01: O=C(OCc1ccccc1)NC(C(=O)NC(C(=O)NC(C(=O)NN(C(=O)CCC(=O)N3c2ccccc2CCC3)CC(=O)O)C(O)C)CCC(=O)O)CC(C)C
• CACTVS 3.370: CC(C)C[CH](NC(=O)OCc1ccccc1)C(=O)N[CH](CCC(O)=O)C(=O)N[CH]([CH](C)O)C(=O)NN(CC(O)=O)C(=O)CCC(=O)N2CCCc3ccccc23
• OpenEye OEToolkits 1.7.6: CC(C)CC(C(=O)NC(CCC(=O)O)C(=O)NC(C(C)O)C(=O)NN(CC(=O)O)C(=O)CCC(=O)N1CCCc2c1cccc2)NC(=O)OCc3ccccc3

SMILES CANONICAL

• CACTVS 3.370: CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NN(CC(O)=O)C(=O)CCC(=O)N2CCCc3ccccc23
• OpenEye OEToolkits 1.7.6: C[C@H]([C@@H](C(=O)NN(CC(=O)O)C(=O)CCC(=O)N1CCCc2c1cccc2)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)OCc3ccccc3)O

InChI

• InChI 1.03: InChI=1S/C38H50N6O12/c1-23(2)20-28(40-38(55)56-22-25-10-5-4-6-11-25)36(53)39-27(15-18-32(48)49)35(52)41-34(24(3)45)37(54)42-44(21-33(50)51)31(47)17-16-30(46)43-19-9-13-26-12-7-8-14-29(26)43/h4-8,10-12,14,23-24,27-28,34,45H,9,13,15-22H2,1-3H3,(H,39,53)(H,40,55)(H,41,52)(H,42,54)(H,48,49)(H,50,51)

InChIKey

• InChI 1.03: FRKMBEAEOZPCDQ-UHFFFAOYSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: (5S,8R,11S)-8-(2-carboxyethyl)-14-[4-(3,4-dihydroquinolin-1(2H)-yl)-4-oxobutanoyl]-11-[(1R)-1-hydroxyethyl]-5-(2-methylpropyl)-3,6,9,12-tetraoxo-1-phenyl-2-oxa-4,7,10,13,14-pentaazahexadecan-16-oic acid (non-preferred name)
• OpenEye OEToolkits 1.7.6: (4S)-5-[[(2S,3R)-1-[2-[4-(3,4-dihydro-2H-quinolin-1-yl)-4-oxidanylidene-butanoyl]-2-(2-hydroxy-2-oxoethyl)hydrazinyl]-3-oxidanyl-1-oxidanylidene-butan-2-yl]amino]-4-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]-5-oxidanylidene-pentanoic acid

PDB entries

Showing all 1 items

PDB-2c2z:
Crystal structure of caspase-8 in complex with aza-peptide Michael acceptor inhibitor