BIRD-PRD_000400: SUCCINYL-ALA-PRO-ALA-P-NITROANILIDE

Basic information

• Entry: Database: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000400
• Status: Status: REF ONLY
• Name: SUCCINYL-ALA-PRO-ALA-P-NITROANILIDE

BIRD information

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

Synonyms

• L-Alaninamide, N-(3-carboxy-1-oxopropyl)-L-alanyl-L-prolyl-N-(4-nitrophenyl)-(9CI) (Scifinder)
• N-((S)-1-Methyl-2-{(S)-2-[(S)-1-(4-nitro-phenylcarbamoyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-succinamic acid (Beilstein)
• Succinyl-Ala-Pro-Ala-p-nitroanilide (Scifinder)
• suc-Ala-Pro-Ala-pNA (Beilstein)

Annotation

• Function: Inhibitor of CYCLOPHILIN B, EC: 5.2.1.8EC: Inhibitor of CYCLOPHILIN B, EC: 5.2.1.8 / Info source: PubMed: 15355356

External info

• ChemSpider: 4484002
• PubChem: 5326631

Family

SUCCINYL peptide tetrahedral intermediate forming peptide inhibitors

BIRD: PRD_000350 / BIRD: PRD_000351 / N-(3-carboxypropanoyl)-L-alanyl-L-alanyl-L-prolyl-6-ammonio-N-(4-nitrophenyl)-L-norleucinamide / BIRD: PRD_000354 / SUCCINYL-ALA-PRO-ALA-P-NITROANILIDE

Chemical information

Composition

Formula: C₂₁H₂₇N₅O₈ / Formula weight: 477.468

• Others: Type: peptide-like

History

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

Details

SMILES

• ACDLabs 12.01: O=C(NC(C(=O)Nc1ccc([N+]([O-])=O)cc1)C)C2N(C(=O)C(NC(=O)CCC(=O)O)C)CCC2
• CACTVS 3.370: C[CH](NC(=O)[CH]1CCCN1C(=O)[CH](C)NC(=O)CCC(O)=O)C(=O)Nc2ccc(cc2)[N+]([O-])=O
• OpenEye OEToolkits 1.7.6: CC(C(=O)Nc1ccc(cc1)[N+](=O)[O-])NC(=O)C2CCCN2C(=O)C(C)NC(=O)CCC(=O)O

SMILES CANONICAL

• CACTVS 3.370: C[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H](C)NC(=O)CCC(O)=O)C(=O)Nc2ccc(cc2)[N+]([O-])=O
• OpenEye OEToolkits 1.7.6: C[C@@H](C(=O)Nc1ccc(cc1)[N+](=O)[O-])NC(=O)[C@@H]2CCCN2C(=O)[C@H](C)NC(=O)CCC(=O)O

InChI

• InChI 1.03: InChI=1S/C21H27N5O8/c1-12(19(30)24-14-5-7-15(8-6-14)26(33)34)23-20(31)16-4-3-11-25(16)21(32)13(2)22-17(27)9-10-18(28)29/h5-8,12-13,16H,3-4,9-11H2,1-2H3,(H,22,27)(H,23,31)(H,24,30)(H,28,29)/t12-,13-,16-/m0/s1

InChIKey

• InChI 1.03: NRPFSJAQJJYJLT-XEZPLFJOSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: N-(3-carboxypropanoyl)-L-alanyl-L-prolyl-N-(4-nitrophenyl)-L-alaninamide
• OpenEye OEToolkits 1.7.6: 4-[[(2S)-1-[(2S)-2-[[(2S)-1-[(4-nitrophenyl)amino]-1-oxidanylidene-propan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxidanylidene-propan-2-yl]amino]-4-oxidanylidene-butanoic acid

PDB entries

Showing all 2 items

PDB-1lop:
CYCLOPHILIN A COMPLEXED WITH SUCCINYL-ALA-PRO-ALA-P-NITROANILIDE

PDB-1v9t:
Structure of E. coli cyclophilin B K163T mutant bound to succinyl-ALA-PRO-ALA-P-nitroanilide