BIRD-PRD_000289: BETA-SECRETASE INHIBITOR OM00-3

Basic information

• Entry: Database: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000289
• Status: Status: REF ONLY
• Name: BETA-SECRETASE INHIBITOR OM00-3

BIRD information

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

Synonyms

• (4S)-4-[(2S)-2-[(2R,4S,5S)-5-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-carboxybutanamido]-4-methylpentanamido]-3-carboxypropanamido]-4-hydroxy-2,7-dimethyloctanamido]-3-methylbutanamido]-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl} butanoic acid (PubChem)
• (4S)-4-amino-5-[[(2S)-1-[[(2S)-4-hydroxy-1-[[(4S,5S,7R)-5-hydroxy-8-[[(2S)-1-[[(2S)-5-hydroxy-1-[[(2S)-1-hydroxy-1-oxo-3-phenylpropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-2,7-dimethyl-8-oxooctan-4-yl]amino]-1,4-dioxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-oxopentanoic acid (PubChem)
• L-Phenylalanine, L-alpha-glutamyl-L-leucyl-L-alpha-aspartyl-(2R,4S,5S)-5-amino-4-hydroxy-2,7-dimethyloctanoyl-L-valyl-L-alpha-glutamyl- (Scifinder)
• OM-00-3 (PubChem)
• OM00-3 (PDB)

Annotation

• Function: beta-secretase inhibitor / Info source: PubMed: 12749695

External info

• ChemSpider: 394264
• ChEBI: 200570
• ChEBI: 491857
• PubChem: 44305509
• PubChem: 447068

Family

Leu-hydroxyethylene isostere containing INHIBITOR

BETA-SECRETASE INHIBITOR OM00-3 / BETA-SECRETASE INHIBITOR OM99-2 / BETA-SECRETASE INHIBITOR NVP-AUR200 / BETA-SECRETASE INHIBITOR NVP-AMK640

Chemical information

Composition

Formula: C₄₄H₆₉N₇O₁₅ / Formula weight: 936.057

• Others: Type: peptide-like

History

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

Details

SMILES

• ACDLabs 12.01: O=C(O)CCC(N)C(=O)NC(C(=O)NC(C(=O)NC(CC(C)C)C(O)CC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)O)Cc1ccccc1)CCC(=O)O)C(C)C)C)CC(=O)O)CC(C)C
• CACTVS 3.370: CC(C)C[CH](NC(=O)[CH](CC(O)=O)NC(=O)[CH](CC(C)C)NC(=O)[CH](N)CCC(O)=O)[CH](O)C[CH](C)C(=O)N[CH](C(C)C)C(=O)N[CH](CCC(O)=O)C(=O)N[CH](Cc1ccccc1)C(O)=O
• OpenEye OEToolkits 1.7.6: CC(C)CC(C(CC(C)C(=O)NC(C(C)C)C(=O)NC(CCC(=O)O)C(=O)NC(Cc1ccccc1)C(=O)O)O)NC(=O)C(CC(=O)O)NC(=O)C(CC(C)C)NC(=O)C(CCC(=O)O)N

SMILES CANONICAL

• CACTVS 3.370: CC(C)C[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCC(O)=O)[C@@H](O)C[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](Cc1ccccc1)C(O)=O
• OpenEye OEToolkits 1.7.6: C[C@H](C[C@H]([C@H](CC(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(=O)O)N)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)O

InChI

• InChI 1.03: InChI=1S/C44H69N7O15/c1-22(2)17-29(47-42(63)31(21-36(57)58)49-41(62)30(18-23(3)4)48-39(60)27(45)13-15-34(53)54)33(52)19-25(7)38(59)51-37(24(5)6)43(64)46-28(14-16-35(55)56)40(61)50-32(44(65)66)20-26-11-9-8-10-12-26/h8-12,22-25,27-33,37,52H,13-21,45H2,1-7H3,(H,46,64)(H,47,63)(H,48,60)(H,49,62)(H,50,61)(H,51,59)(H,53,54)(H,55,56)(H,57,58)(H,65,66)/t25-,27-,28?,29-,30-,31+,32?,33+,37?/m0/s1

InChIKey

• InChI 1.03: CFIWWTUUSMMDDA-BQWRNDNKSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: (2R,5R,8S,11S,13R,14S,17R,20S,23S)-23-amino-2-benzyl-5-(2-carboxyethyl)-17-(carboxymethyl)-13-hydroxy-11-methyl-14,20-bis(2-methylpropyl)-4,7,10,16,19,22-hexaoxo-8-(propan-2-yl)-3,6,9,15,18,21-hexaazahexacosane-1,26-dioic acid (non-preferred name)
• OpenEye OEToolkits 1.7.6: (4S)-4-azanyl-5-[[(2S)-1-[[(2S)-1-[[(4S,5R,7R)-2,7-dimethyl-8-[[(2S)-3-methyl-1-[[(2S)-5-oxidanyl-1,5-bis(oxidanylidene)-1-[[(2S)-1-oxidanyl-1-oxidanylidene-3-phenyl-propan-2-yl]amino]pentan-2-yl]amino]-1-oxidanylidene-butan-2-yl]amino]-5-oxidanyl-8-oxidanylidene-octan-4-yl]amino]-4-oxidanyl-1,4-bis(oxidanylidene)butan-2-yl]amino]-4-methyl-1-oxidanylidene-pentan-2-yl]amino]-5-oxidanylidene-pentanoic acid

PDB entries

Showing all 1 items

PDB-1m4h:
Crystal Structure of Beta-secretase complexed with Inhibitor OM00-3