phosphoramidon

Also known as (2S)-2-{[(2S)-2-{[(S)-hydroxy{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}phosphoryl]amino}-4-methylpentanoyl]amino}-3-(1H-indol-3-yl)propanoic acid (non-preferred name), N-(N-(((6-deoxy-alpha-L-mannopyranosyl)oxy)hydroxyphosphinyl)-L-leucyl)-L-tryptophan

Phosphoramidon is a chemical compound derived from cultures of Streptomyces tanashiensis. It is an inhibitor of the enzyme thermolysin, of the membrane metallo-endopeptidase, and of the endothelin converting enzyme. Chemically, phosphoramidon differs from its closely related peptidase inhibitor talopeptin by a single stereocenter.

Chemical data

Formula: C23H34N3O10P
Molecular weight: 543.5 g/mol
IUPAC name: (2S)-2-[[(2S)-2-[[hydroxy-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphosphoryl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid
SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OP(=O)(N[C@@H](CC(C)C)C(=O)N[C@@H](CC2=CNC3=CC=CC=C32)C(=O)O)O)O)O)O
InChIKey: ZPHBZEQOLSRPAK-XLCYBJAPSA-N
XLogP: -0.2
Polar surface area: 211 Å²
H-bond donors: 8
H-bond acceptors: 11
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Mass: 543.198

Show 4 more facts

chemical formula: C₂₃H₃₄N₃O₁₀P
isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OP(=O)(N[C@@H](CC(C)C)C(=O)N[C@@H](CC2=CNC3=CC=CC=C32)C(=O)O)O)O)O)O
canonical SMILES: CC1C(C(C(C(O1)OP(=O)(NC(CC(C)C)C(=O)NC(CC2=CNC3=CC=CC=C32)C(=O)O)O)O)O)O
subject has role: protease inhibitor

Sources (3)

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Encyclopedic overview

2 sections

Contents

References
External links

Because of its enzyme inhibitory properties, phosphoramidon is widely used as a biochemical tool.

Excerpted from Wikipedia’s “phosphoramidon” article, available under the CC BY-SA 4.0 licence.

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