BIRD-PRD_000770: (5S, 8R, 11S)-14-[4-(BENZYLOXY)-4-OXOBUTANOYL]-8-(2-CARBOXYETHYL)...

Basic information

• Entry: Database: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000770
• Status: Status: REF ONLY
• Name: (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

BIRD information

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

Annotation

• Function: aza-peptide Michael acceptor inhibitor of CASPASE-3, EC: 3.4.22.56EC: aza-peptide Michael acceptor inhibitor of CASPASE-3, EC: 3.4.22.56 / Info source: PubMed: 16970398

External info

• ChemSpider: 7828112
• PubChem: 9549190

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: C₃₅H₄₃N₅O₁₄ / Formula weight: 757.741

• Others: Type: peptide-like

History

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

Details

SMILES

• ACDLabs 12.01: O=C(OCc1ccccc1)CCC(=O)N(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)OCc2ccccc2)CC(=O)O)CCC(=O)O)C(C)C)CC(=O)O
• CACTVS 3.370: CC(C)[CH](NC(=O)[CH](CCC(O)=O)NC(=O)[CH](CC(O)=O)NC(=O)OCc1ccccc1)C(=O)NN(CC(O)=O)C(=O)CCC(=O)OCc2ccccc2
• OpenEye OEToolkits 1.7.6: CC(C)C(C(=O)NN(CC(=O)O)C(=O)CCC(=O)OCc1ccccc1)NC(=O)C(CCC(=O)O)NC(=O)C(CC(=O)O)NC(=O)OCc2ccccc2

SMILES CANONICAL

• CACTVS 3.370: CC(C)[C@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)OCc1ccccc1)C(=O)NN(CC(O)=O)C(=O)CCC(=O)OCc2ccccc2
• OpenEye OEToolkits 1.7.6: CC(C)[C@@H](C(=O)NN(CC(=O)O)C(=O)CCC(=O)OCc1ccccc1)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)OCc2ccccc2

InChI

• InChI 1.03: InChI=1S/C35H43N5O14/c1-21(2)31(34(51)39-40(18-29(46)47)26(41)14-16-30(48)53-19-22-9-5-3-6-10-22)38-32(49)24(13-15-27(42)43)36-33(50)25(17-28(44)45)37-35(52)54-20-23-11-7-4-8-12-23/h3-12,21,24-25,31H,13-20H2,1-2H3,(H,36,50)(H,37,52)(H,38,49)(H,39,51)(H,42,43)(H,44,45)(H,46,47)

InChIKey

• InChI 1.03: FQWQWWLJENCPGF-UHFFFAOYSA-N

SYSTEMATIC NAME

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

PDB entries

Showing all 1 items

PDB-2c2m:
Crystal structures of caspase-3 in complex with aza-peptide Michael acceptor inhibitors.